v2.2.5

Upgrade the `@react-email/render` package to handle
suspense during renders.

We could have just swapped to `renderAsync` for the 0.0.x
version of the package but it's better to upgrade as part
of this change.

CI has been run locally and emails have been verified to
work and render as expected in our local mail trap.

.env.example

@@ -147,6 +147,15 @@ NEXT_PUBLIC_USE_INTERNAL_URL_BROWSERLESS=false
 # We only collect: app version, installation ID, and node ID. No personal data is collected.
 DOCUMENSO_DISABLE_TELEMETRY=
 
+# [[AI]]
+# OPTIONAL: Google Cloud Project ID for Vertex AI.
+GOOGLE_VERTEX_PROJECT_ID=""
+# OPTIONAL: Google Cloud region for Vertex AI. Defaults to "global".
+GOOGLE_VERTEX_LOCATION="global"
+# OPTIONAL: API key for Google Vertex AI (Gemini). Get your key from:
+# https://console.cloud.google.com/vertex-ai/studio/settings/api-keys
+GOOGLE_VERTEX_API_KEY=""
+
 # [[E2E Tests]]
 E2E_TEST_AUTHENTICATE_USERNAME="Test User"
 E2E_TEST_AUTHENTICATE_USER_EMAIL="testuser@mail.com"
@@ -157,4 +166,4 @@ E2E_TEST_AUTHENTICATE_USER_PASSWORD="test_Password123"
 NEXT_PRIVATE_LOGGER_FILE_PATH=
 
 # [[PLAIN SUPPORT]]
-NEXT_PRIVATE_PLAIN_API_KEY=
+NEXT_PRIVATE_PLAIN_API_KEY=

.github/workflows/e2e-tests.yml

@@ -1,14 +1,19 @@
 name: Playwright Tests
 on:
   push:
-    branches: ['main', 'feat/rr7']
+    branches: ['main']
   pull_request:
     branches: ['main']
+
+concurrency:
+  group: ci-${{ github.workflow }}-${{ github.ref }}
+  cancel-in-progress: true
+
 jobs:
   e2e_tests:
     name: 'E2E Tests'
     timeout-minutes: 60
-    runs-on: warp-ubuntu-2204-x64-16x
+    runs-on: warp-ubuntu-2204-x64-8x
     steps:
       - uses: actions/checkout@v4
 
@@ -28,9 +33,6 @@ jobs:
       - name: Seed the database
         run: npm run prisma:seed
 
-      - name: Build app
-        run: npm run build
-
       - name: Install playwright browsers
         run: npx playwright install --with-deps
 
@@ -45,7 +47,7 @@ jobs:
         with:
           name: test-results
           path: 'packages/app-tests/**/test-results/*'
-          retention-days: 30
+          retention-days: 7
     env:
       TURBO_TOKEN: ${{ secrets.TURBO_TOKEN }}
       TURBO_TEAM: ${{ vars.TURBO_TEAM }}

.github/workflows/translations-upload.yml

@@ -17,6 +17,7 @@ jobs:
     environment: Translations
     permissions:
       contents: write
+      pull-requests: write
     steps:
       - name: Checkout
         uses: actions/checkout@v4
@@ -26,12 +27,54 @@ jobs:
       - name: Extract translations
         run: npm run translate:extract
 
-      - name: Check and commit any files created
+      - name: Commit changes and push to reserved branch
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
         run: |
+          set -euo pipefail
+
+          BRANCH="chore/extract-translations"
+
           git config --global user.name 'github-actions'
           git config --global user.email 'github-actions@documenso.com'
+
+          git fetch origin
+
+          # Create branch locally (always reset to main)
+          git checkout -B "$BRANCH" origin/main
+
+          # Stage translation output
           git add packages/lib/translations
-          git diff --staged --quiet --exit-code || (git commit -m "chore: extract translations" && git push)
+
+          # If no changes, exit early
+          if git diff --staged --quiet; then
+            echo "No translation changes found."
+            exit 0
+          fi
+
+          # Commit fresh snapshot
+          git commit -m "chore: extract translations"
+
+          # Force push reserved branch
+          git push origin "$BRANCH" --force
+
+          # Does a PR already exist?
+          EXISTING_PR=$(gh pr list \
+            --state open \
+            --head "$BRANCH" \
+            --json number \
+            --jq '.[0].number // empty')
+
+          if [ -z "$EXISTING_PR" ]; then
+            echo "No existing PR — creating new one."
+            gh pr create \
+              --title "chore: extract translations" \
+              --body "Automated translation extraction" \
+              --base main \
+              --head "$BRANCH"
+          else
+            echo "PR #$EXISTING_PR already exists — not creating a new one."
+          fi
 
       - name: Compile translations
         id: compile_translations

.gitignore

@@ -60,3 +60,6 @@ CLAUDE.md
 
 # agents
 .specs
+
+# scripts
+scripts/output*

README.md

@@ -1,6 +1,3 @@
-> 🚨 🚨 🚨
-> Documenso 2.0.0 is live on Product Hunt 🎉 <a href="https://documen.so/launch" target="_blank" rel="noopener noreferrer" style="text-decoration: underline;">Join us to celebrate the best Documenso yet 🪩</a>
-
 <img src="https://github.com/documenso/documenso/assets/13398220/a643571f-0239-46a6-a73e-6bef38d1228b" alt="Documenso Logo">
 
 <p align="center" style="margin-top: 20px">
@@ -174,9 +171,11 @@ git clone https://github.com/<your-username>/documenso
 
 5. Create the database schema by running `npm run prisma:migrate-dev`
 
-6. Run `npm run dev` in the root directory to start
+6. Run `npm run translate:compile` in the root directory to compile lingui
 
-7. Register a new user at http://localhost:3000/signup
+7. Run `npm run dev` in the root directory to start
+
+8. Register a new user at http://localhost:3000/signup
 
 ---
 

apps/documentation/package.json

@@ -15,7 +15,7 @@
     "@documenso/tailwind-config": "*",
     "@documenso/trpc": "*",
     "@documenso/ui": "*",
-    "next": "^15",
+    "next": "^15.5.7",
     "next-plausible": "^3.12.5",
     "nextra": "^3",
     "nextra-theme-docs": "^3",

apps/documentation/pages/developers/self-hosting/_meta.js

@@ -4,4 +4,5 @@ export default {
   'how-to': 'How To',
   'setting-up-oauth-providers': 'Setting up OAuth Providers',
   telemetry: 'Telemetry',
+  'ai-features': 'AI Recipient & Field Detection',
 };

apps/documentation/pages/developers/self-hosting/ai-features.mdx

@@ -0,0 +1,72 @@
+---
+title: AI Recipient & Field Detection (Self-hosting)
+description: Configure Google Vertex AI so Documenso can detect recipients and fields automatically.
+---
+
+import { Callout, Steps } from 'nextra/components';
+
+# AI Recipient & Field Detection (Self-hosting)
+
+This guide covers how to enable the AI recipient and field detection features when you self-host Documenso.
+
+## What this enables
+
+- Detect recipients from uploaded PDFs (roles, names, emails when present).
+- Detect and place fields (signature, initials, name, email, date, text, number, radio, checkbox) onto draft envelopes.
+- Built-in rate limits (3 requests per minute per IP) to prevent abuse.
+
+## Prerequisites
+
+- A Google Cloud project with the **Vertex AI API** enabled and billing active.
+- A **Vertex AI Express API key** with access to Gemini models (create via the [Vertex AI Express flow](https://cloud.google.com/vertex-ai/generative-ai/docs/start/express-mode/overview) and manage keys in [API keys](https://cloud.google.com/vertex-ai/generative-ai/docs/start/api-keys)).
+- Documenso version that includes the AI detection feature and the corresponding database migration.
+
+## Configure environment variables
+
+Add these variables to your deployment `.env` (or secret manager):
+
+```
+GOOGLE_VERTEX_PROJECT_ID="<your-gcp-project-id>"
+GOOGLE_VERTEX_API_KEY="<your-vertex-api-key>"
+# Optional, defaults to "global"
+GOOGLE_VERTEX_LOCATION="global"
+```
+
+<Callout type="info">
+  Use a region close to your users if you need data residency considerations (e.g. `europe-west1`).
+  If you omit the location, Documenso uses `global`. Not all models are available in every region;
+  if a model is unavailable, switch to a supported region.
+</Callout>
+
+## Deploy with the published container
+
+- Use the official Documenso image (DockerHub or GHCR) and supply the Vertex env vars above.
+- Ensure migrations run on startup (the container runs `prisma migrate deploy` in production mode).
+- Restart the container after adding or changing Vertex env vars.
+
+## Enable the feature in Documenso
+
+Once the service is running with the Vertex env vars:
+
+<Steps>
+### Organisation settings
+
+Go to **Settings → Document Preferences → AI Features** and set to **Enabled**. Teams that inherit organisation defaults will pick this up.
+
+### Team settings
+
+If a team overrides organisation defaults, go to **Team Settings → Document Preferences → AI Features** and choose **Enabled** (or **Inherit** to follow the organisation).
+
+### Verify in the editor
+
+Open a draft envelope. In **Recipients**, you should see the sparkle button for AI detection. In **Fields**, you should see **Detect with AI** available.
+
+</Steps>
+
+## Troubleshooting
+
+- **Too many requests**: Wait a minute or two and retry (rate limit is 3/min per IP).
+- **AI options hidden**: Ensure the env vars are set, the server was restarted after setting them, and `aiFeaturesEnabled` is enabled at organisation/team level.
+- **Detection fails immediately**: Confirm the Vertex API key is valid and the project has Vertex AI enabled. Check server logs for status codes from Vertex.
+
+If issues persist, recheck env vars, restart the service, and confirm the Prisma migration was applied.

apps/documentation/pages/developers/self-hosting/how-to.mdx

@@ -119,6 +119,8 @@ NEXT_PRIVATE_SMTP_USERNAME="<your-username>"
 NEXT_PRIVATE_SMTP_PASSWORD="<your-password>"
 ```
 
+For full AI setup details (including model availability notes), see the [AI Recipient & Field Detection (Self-hosting)](./ai-features) page.
+
 ### Set Up Your Signing Certificate
 
 <Callout type="warning">
@@ -267,58 +269,63 @@ You can access the Documenso application by visiting the URL you provided for th
 
 The environment variables listed above are a subset of those available for configuring Documenso. The table below provides a complete list of environment variables and their descriptions.
 
-| Variable                                     | Description                                                                                         |
-| -------------------------------------------- | --------------------------------------------------------------------------------------------------- |
-| `PORT`                                       | The port on which the Documenso application runs. It defaults to `3000`.                            |
-| `NEXTAUTH_SECRET`                            | The secret key used by NextAuth.js for encryption and signing.                                      |
-| `NEXT_PRIVATE_ENCRYPTION_KEY`                | The primary encryption key for symmetric encryption and decryption (at least 32 characters).        |
-| `NEXT_PRIVATE_ENCRYPTION_SECONDARY_KEY`      | The secondary encryption key for symmetric encryption and decryption (at least 32 characters).      |
-| `NEXT_PRIVATE_GOOGLE_CLIENT_ID`              | The Google client ID for Google authentication (optional).                                          |
-| `NEXT_PRIVATE_GOOGLE_CLIENT_SECRET`          | The Google client secret for Google authentication (optional).                                      |
-| `NEXT_PRIVATE_MICROSOFT_CLIENT_ID`           | The Microsoft client ID for Microsoft authentication (optional).                                    |
-| `NEXT_PRIVATE_MICROSOFT_CLIENT_SECRET`       | The Microsoft client secret for Microsoft authentication (optional).                                |
-| `NEXT_PRIVATE_OIDC_CLIENT_ID`                | The OIDC client ID for OIDC authentication (optional).                                              |
-| `NEXT_PRIVATE_OIDC_CLIENT_SECRET`            | The OIDC client secret for OIDC authentication (optional).                                          |
-| `NEXT_PRIVATE_OIDC_WELL_KNOWN`               | The well-known URL for the OIDC provider (optional).                                                |
-| `NEXT_PRIVATE_OIDC_PROVIDER_LABEL`           | The label to display for the OIDC provider button (optional).                                       |
-| `NEXT_PRIVATE_OIDC_SKIP_VERIFY`              | Whether to skip email verification for OIDC accounts (optional, default `false`).                   |
-| `NEXT_PUBLIC_WEBAPP_URL`                     | The URL for the web application.                                                                    |
-| `NEXT_PUBLIC_SUPPORT_EMAIL`                  | The support email address displayed to users (default `support@documenso.com`).                     |
-| `NEXT_PRIVATE_DATABASE_URL`                  | The URL for the primary database connection (with connection pooling).                              |
-| `NEXT_PRIVATE_DIRECT_DATABASE_URL`           | The URL for the direct database connection (without connection pooling).                            |
-| `NEXT_PRIVATE_SIGNING_TRANSPORT`             | The signing transport to use. Available options: local (default)                                    |
-| `NEXT_PRIVATE_SIGNING_PASSPHRASE`            | The passphrase for the key file.                                                                    |
-| `NEXT_PRIVATE_SIGNING_LOCAL_FILE_CONTENTS`   | The base64-encoded contents of the key file will be used instead of the file path.                  |
-| `NEXT_PRIVATE_SIGNING_LOCAL_FILE_PATH`       | The path to the key file, default `/opt/documenso/cert.p12`.                                        |
-| `NEXT_PUBLIC_UPLOAD_TRANSPORT`               | The transport for file uploads (database or s3).                                                    |
-| `NEXT_PRIVATE_UPLOAD_ENDPOINT`               | The endpoint for the S3 storage transport (for third-party S3-compatible providers).                |
-| `NEXT_PRIVATE_UPLOAD_FORCE_PATH_STYLE`       | Whether to force path-style URLs for the S3 storage transport.                                      |
-| `NEXT_PRIVATE_UPLOAD_REGION`                 | The region for the S3 storage transport (defaults to us-east-1).                                    |
-| `NEXT_PRIVATE_UPLOAD_BUCKET`                 | The bucket to use for the S3 storage transport.                                                     |
-| `NEXT_PRIVATE_UPLOAD_ACCESS_KEY_ID`          | The access key ID for the S3 storage transport.                                                     |
-| `NEXT_PRIVATE_UPLOAD_SECRET_ACCESS_KEY`      | The secret access key for the S3 storage transport.                                                 |
-| `NEXT_PRIVATE_SMTP_TRANSPORT`                | The transport to send emails (smtp-auth, smtp-api, resend, or mailchannels).                        |
-| `NEXT_PRIVATE_SMTP_HOST`                     | The host for the SMTP server for SMTP transports.                                                   |
-| `NEXT_PRIVATE_SMTP_PORT`                     | The port for the SMTP server for SMTP transports.                                                   |
-| `NEXT_PRIVATE_SMTP_USERNAME`                 | The username for the SMTP server for the `smtp-auth` transport.                                     |
-| `NEXT_PRIVATE_SMTP_PASSWORD`                 | The password for the SMTP server for the `smtp-auth` transport.                                     |
-| `NEXT_PRIVATE_SMTP_APIKEY_USER`              | The API key user for the SMTP server for the `smtp-api` transport.                                  |
-| `NEXT_PRIVATE_SMTP_APIKEY`                   | The API key for the SMTP server for the `smtp-api` transport.                                       |
-| `NEXT_PRIVATE_SMTP_SECURE`                   | Whether to force the use of TLS for the SMTP server for SMTP transports.                            |
-| `NEXT_PRIVATE_SMTP_UNSAFE_IGNORE_TLS`        | Whether to ignore TLS errors for the SMTP server (useful for self-signed certificates).             |
-| `NEXT_PRIVATE_SMTP_FROM_ADDRESS`             | The email address for the "from" address.                                                           |
-| `NEXT_PRIVATE_SMTP_FROM_NAME`                | The sender name for the "from" address.                                                             |
-| `NEXT_PRIVATE_RESEND_API_KEY`                | The API key for Resend.com for the `resend` transport.                                              |
-| `NEXT_PRIVATE_MAILCHANNELS_API_KEY`          | The optional API key for MailChannels (if using a proxy) for the `mailchannels` transport.          |
-| `NEXT_PRIVATE_MAILCHANNELS_ENDPOINT`         | The optional endpoint for the MailChannels API (if using a proxy) for the `mailchannels` transport. |
-| `NEXT_PRIVATE_MAILCHANNELS_DKIM_DOMAIN`      | The domain for DKIM signing with MailChannels for the `mailchannels` transport.                     |
-| `NEXT_PRIVATE_MAILCHANNELS_DKIM_SELECTOR`    | The selector for DKIM signing with MailChannels for the `mailchannels` transport.                   |
-| `NEXT_PRIVATE_MAILCHANNELS_DKIM_PRIVATE_KEY` | The private key for DKIM signing with MailChannels for the `mailchannels` transport.                |
-| `NEXT_PUBLIC_DOCUMENT_SIZE_UPLOAD_LIMIT`     | The maximum document upload limit displayed to the user (in MB).                                    |
-| `NEXT_PUBLIC_POSTHOG_KEY`                    | The optional PostHog key for analytics and feature flags.                                           |
-| `NEXT_PUBLIC_DISABLE_SIGNUP`                 | Whether to disable user signups through the /signup page.                                           |
-| `NEXT_PRIVATE_BROWSERLESS_URL`               | The URL for a Browserless.io instance to generate PDFs (optional).                                  |
-| `DOCUMENSO_DISABLE_TELEMETRY`                | Set to `true` to disable anonymous telemetry (see [Telemetry](#telemetry) section below).           |
+For AI setup specifics, see the [AI Recipient & Field Detection (Self-hosting)](./ai-features) page.
+
+| Variable                                     | Description                                                                                                                                             |
+| -------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------- |
+| `PORT`                                       | The port on which the Documenso application runs. It defaults to `3000`.                                                                                |
+| `NEXTAUTH_SECRET`                            | The secret key used by NextAuth.js for encryption and signing.                                                                                          |
+| `NEXT_PRIVATE_ENCRYPTION_KEY`                | The primary encryption key for symmetric encryption and decryption (at least 32 characters).                                                            |
+| `NEXT_PRIVATE_ENCRYPTION_SECONDARY_KEY`      | The secondary encryption key for symmetric encryption and decryption (at least 32 characters).                                                          |
+| `NEXT_PRIVATE_GOOGLE_CLIENT_ID`              | The Google client ID for Google authentication (optional).                                                                                              |
+| `NEXT_PRIVATE_GOOGLE_CLIENT_SECRET`          | The Google client secret for Google authentication (optional).                                                                                          |
+| `NEXT_PRIVATE_MICROSOFT_CLIENT_ID`           | The Microsoft client ID for Microsoft authentication (optional).                                                                                        |
+| `NEXT_PRIVATE_MICROSOFT_CLIENT_SECRET`       | The Microsoft client secret for Microsoft authentication (optional).                                                                                    |
+| `NEXT_PRIVATE_OIDC_CLIENT_ID`                | The OIDC client ID for OIDC authentication (optional).                                                                                                  |
+| `NEXT_PRIVATE_OIDC_CLIENT_SECRET`            | The OIDC client secret for OIDC authentication (optional).                                                                                              |
+| `NEXT_PRIVATE_OIDC_WELL_KNOWN`               | The well-known URL for the OIDC provider (optional).                                                                                                    |
+| `NEXT_PRIVATE_OIDC_PROVIDER_LABEL`           | The label to display for the OIDC provider button (optional).                                                                                           |
+| `NEXT_PRIVATE_OIDC_SKIP_VERIFY`              | Whether to skip email verification for OIDC accounts (optional, default `false`).                                                                       |
+| `NEXT_PUBLIC_WEBAPP_URL`                     | The URL for the web application.                                                                                                                        |
+| `NEXT_PUBLIC_SUPPORT_EMAIL`                  | The support email address displayed to users (default `support@documenso.com`).                                                                         |
+| `NEXT_PRIVATE_DATABASE_URL`                  | The URL for the primary database connection (with connection pooling).                                                                                  |
+| `NEXT_PRIVATE_DIRECT_DATABASE_URL`           | The URL for the direct database connection (without connection pooling).                                                                                |
+| `NEXT_PRIVATE_SIGNING_TRANSPORT`             | The signing transport to use. Available options: local (default)                                                                                        |
+| `NEXT_PRIVATE_SIGNING_PASSPHRASE`            | The passphrase for the key file.                                                                                                                        |
+| `NEXT_PRIVATE_SIGNING_LOCAL_FILE_CONTENTS`   | The base64-encoded contents of the key file will be used instead of the file path.                                                                      |
+| `NEXT_PRIVATE_SIGNING_LOCAL_FILE_PATH`       | The path to the key file, default `/opt/documenso/cert.p12`.                                                                                            |
+| `NEXT_PUBLIC_UPLOAD_TRANSPORT`               | The transport for file uploads (database or s3).                                                                                                        |
+| `NEXT_PRIVATE_UPLOAD_ENDPOINT`               | The endpoint for the S3 storage transport (for third-party S3-compatible providers).                                                                    |
+| `NEXT_PRIVATE_UPLOAD_FORCE_PATH_STYLE`       | Whether to force path-style URLs for the S3 storage transport.                                                                                          |
+| `NEXT_PRIVATE_UPLOAD_REGION`                 | The region for the S3 storage transport (defaults to us-east-1).                                                                                        |
+| `NEXT_PRIVATE_UPLOAD_BUCKET`                 | The bucket to use for the S3 storage transport.                                                                                                         |
+| `NEXT_PRIVATE_UPLOAD_ACCESS_KEY_ID`          | The access key ID for the S3 storage transport.                                                                                                         |
+| `NEXT_PRIVATE_UPLOAD_SECRET_ACCESS_KEY`      | The secret access key for the S3 storage transport.                                                                                                     |
+| `NEXT_PRIVATE_SMTP_TRANSPORT`                | The transport to send emails (smtp-auth, smtp-api, resend, or mailchannels).                                                                            |
+| `NEXT_PRIVATE_SMTP_HOST`                     | The host for the SMTP server for SMTP transports.                                                                                                       |
+| `NEXT_PRIVATE_SMTP_PORT`                     | The port for the SMTP server for SMTP transports.                                                                                                       |
+| `NEXT_PRIVATE_SMTP_USERNAME`                 | The username for the SMTP server for the `smtp-auth` transport.                                                                                         |
+| `NEXT_PRIVATE_SMTP_PASSWORD`                 | The password for the SMTP server for the `smtp-auth` transport.                                                                                         |
+| `NEXT_PRIVATE_SMTP_APIKEY_USER`              | The API key user for the SMTP server for the `smtp-api` transport.                                                                                      |
+| `NEXT_PRIVATE_SMTP_APIKEY`                   | The API key for the SMTP server for the `smtp-api` transport.                                                                                           |
+| `NEXT_PRIVATE_SMTP_SECURE`                   | Whether to force the use of TLS for the SMTP server for SMTP transports.                                                                                |
+| `NEXT_PRIVATE_SMTP_UNSAFE_IGNORE_TLS`        | Whether to ignore TLS errors for the SMTP server (useful for self-signed certificates).                                                                 |
+| `NEXT_PRIVATE_SMTP_FROM_ADDRESS`             | The email address for the "from" address.                                                                                                               |
+| `NEXT_PRIVATE_SMTP_FROM_NAME`                | The sender name for the "from" address.                                                                                                                 |
+| `NEXT_PRIVATE_RESEND_API_KEY`                | The API key for Resend.com for the `resend` transport.                                                                                                  |
+| `NEXT_PRIVATE_MAILCHANNELS_API_KEY`          | The optional API key for MailChannels (if using a proxy) for the `mailchannels` transport.                                                              |
+| `NEXT_PRIVATE_MAILCHANNELS_ENDPOINT`         | The optional endpoint for the MailChannels API (if using a proxy) for the `mailchannels` transport.                                                     |
+| `NEXT_PRIVATE_MAILCHANNELS_DKIM_DOMAIN`      | The domain for DKIM signing with MailChannels for the `mailchannels` transport.                                                                         |
+| `NEXT_PRIVATE_MAILCHANNELS_DKIM_SELECTOR`    | The selector for DKIM signing with MailChannels for the `mailchannels` transport.                                                                       |
+| `NEXT_PRIVATE_MAILCHANNELS_DKIM_PRIVATE_KEY` | The private key for DKIM signing with MailChannels for the `mailchannels` transport.                                                                    |
+| `NEXT_PUBLIC_DOCUMENT_SIZE_UPLOAD_LIMIT`     | The maximum document upload limit displayed to the user (in MB).                                                                                        |
+| `NEXT_PUBLIC_POSTHOG_KEY`                    | The optional PostHog key for analytics and feature flags.                                                                                               |
+| `NEXT_PUBLIC_DISABLE_SIGNUP`                 | Whether to disable user signups through the /signup page.                                                                                               |
+| `NEXT_PRIVATE_BROWSERLESS_URL`               | The URL for a Browserless.io instance to generate PDFs (optional).                                                                                      |
+| `DOCUMENSO_DISABLE_TELEMETRY`                | Set to `true` to disable anonymous telemetry (see [Telemetry](#telemetry) section below).                                                               |
+| `GOOGLE_VERTEX_PROJECT_ID`                   | Google Cloud project ID used for Vertex AI (required for AI detection).                                                                                 |
+| `GOOGLE_VERTEX_API_KEY`                      | Vertex AI Express API key with access to Gemini models (required for AI detection). See [AI Recipient & Field Detectionfor](./ai-features) for details. |
+| `GOOGLE_VERTEX_LOCATION`                     | Optional Vertex region, defaults to `global`. Not all models are available in every region.                                                             |
 
 ## Telemetry
 

apps/documentation/pages/users/documents/_meta.js

@@ -4,4 +4,5 @@ export default {
   'document-visibility': 'Document Visibility',
   fields: 'Document Fields',
   'email-preferences': 'Email Preferences',
+  'ai-detection': 'AI Recipient & Field Detection',
 };

apps/documentation/pages/users/documents/ai-detection.mdx

@@ -0,0 +1,68 @@
+---
+title: AI Recipient & Field Detection
+description: Use Documenso’s AI helpers to detect recipients and fields in draft documents.
+---
+
+# AI Recipient & Field Detection
+
+Documenso can suggest recipients and place fields automatically using Google Vertex AI (Gemini). The feature is optional and only available when your organisation or team has **AI Features** enabled. Documents are processed securely and providers do not retain your data for training.
+
+## Requirements
+
+- AI Features must be enabled in **Document Preferences** for your organisation or team.
+- The envelope must be in **Draft** status.
+- Helpful rate limits are in place (up to 3 detection requests per minute per IP) to prevent abuse. If you see a “too many requests” message, wait a minute or two and try again.
+
+### Enable AI features
+
+1. **Organisation settings**:
+
+Settings → Document Preferences → **AI Features** → Enabled.
+
+_This applies to teams that inherit organisation defaults._
+
+2. **Team settings**:
+
+Team Settings → Document Preferences → **AI Features** → choose Enabled, Disabled, or Inherit.
+
+## Detect recipients
+
+Use this to identify who needs to sign or approve.
+
+1. Open a draft document/template and go to the **Recipients** panel.
+2. Select the **sparkle** button to start detection. If AI is enabled, uploads launched from the dashboard will open the detector automatically.
+
+![Detect recipients with AI button in the Recipients panel](/document-signing/ai-recipient-detect-button.webp)
+
+3. Wait for progress to finish, then review the suggested recipients.
+4. Remove any incorrect entries, then **Add recipients** to apply them. Existing recipients and duplicates are preserved.
+
+Notes:
+
+- Detection is unavailable once an envelope is completed.
+- You can re-run detection if you update the document; each run counts toward the rate limit.
+
+## Detect fields
+
+Use this to auto-place fields on the pages of a draft.
+
+1. Open the envelope editor and switch to the **Fields** tab.
+2. Select **Detect with AI**. Provide optional context (e.g., “Alice is the tenant, Bob is the landlord”) to improve recipient assignment.
+
+![AI field detection dialog with context input](/document-signing/ai-field-detection-button.webp)
+![AI field detection dialog with context input](/document-signing/ai-field-detection-dialog.webp)
+
+3. Watch the progress indicators; they update per page and total fields found.
+4. Review the summary and choose **Add fields** to place them in the editor.
+
+Notes:
+
+- Works only for draft envelopes and teams with AI features enabled.
+- Existing fields are masked during detection to avoid duplicates.
+- Fields are assigned to recipients based on nearby labels and your context message; you can edit them after adding.
+
+## Best practices
+
+- Keep labels near the intended fields (e.g., “Tenant signature”, “Buyer email”).
+- Provide short context when roles are ambiguous.
+- Always review suggestions before sending; AI assists but does not replace final checks.

apps/openpage-api/package.json

@@ -12,7 +12,7 @@
   "dependencies": {
     "@documenso/prisma": "*",
     "luxon": "^3.7.2",
-    "next": "^15"
+    "next": "^15.5.7"
   },
   "devDependencies": {
     "@types/node": "^20",

apps/remix/app/components/dialogs/admin-document-delete-dialog.tsx

@@ -45,7 +45,7 @@ export const AdminDocumentDeleteDialog = ({ envelopeId }: AdminDocumentDeleteDia
 
       toast({
         title: _(msg`Document deleted`),
-        description: 'The Document has been deleted successfully.',
+        description: _(msg`The Document has been deleted successfully.`),
         duration: 5000,
       });
 
@@ -54,8 +54,9 @@ export const AdminDocumentDeleteDialog = ({ envelopeId }: AdminDocumentDeleteDia
       toast({
         title: _(msg`An unknown error occurred`),
         variant: 'destructive',
-        description:
-          'We encountered an unknown error while attempting to delete your document. Please try again later.',
+        description: _(
+          msg`We encountered an unknown error while attempting to delete your document. Please try again later.`,
+        ),
       });
     }
   };

apps/remix/app/components/dialogs/ai-field-detection-dialog.tsx

@@ -0,0 +1,368 @@
+import { useCallback, useEffect, useMemo, useState } from 'react';
+
+import type { MessageDescriptor } from '@lingui/core';
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
+import { CheckIcon, FormInputIcon, ShieldCheckIcon } from 'lucide-react';
+
+import type { NormalizedFieldWithContext } from '@documenso/lib/server-only/ai/envelope/detect-fields/types';
+import { Alert, AlertDescription } from '@documenso/ui/primitives/alert';
+import { Button } from '@documenso/ui/primitives/button';
+import {
+  Dialog,
+  DialogContent,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '@documenso/ui/primitives/dialog';
+import { Label } from '@documenso/ui/primitives/label';
+import { Textarea } from '@documenso/ui/primitives/textarea';
+
+import {
+  AiApiError,
+  type DetectFieldsProgressEvent,
+  detectFields,
+} from '../../../server/api/ai/detect-fields.client';
+import { AnimatedDocumentScanner } from '../general/animated-document-scanner';
+
+type DialogState = 'PROMPT' | 'PROCESSING' | 'REVIEW' | 'ERROR' | 'RATE_LIMITED';
+
+type AiFieldDetectionDialogProps = {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+  onComplete: (fields: NormalizedFieldWithContext[]) => void;
+  envelopeId: string;
+  teamId: number;
+};
+
+const PROCESSING_MESSAGES = [
+  msg`Reading your document`,
+  msg`Analyzing page layout`,
+  msg`Looking for form fields`,
+  msg`Detecting signature areas`,
+  msg`Identifying input fields`,
+  msg`Mapping fields to recipients`,
+  msg`Almost done`,
+] as const;
+
+const FIELD_TYPE_LABELS: Record<string, MessageDescriptor> = {
+  SIGNATURE: msg`Signature`,
+  INITIALS: msg`Initials`,
+  NAME: msg`Name`,
+  EMAIL: msg`Email`,
+  DATE: msg`Date`,
+  TEXT: msg`Text`,
+  NUMBER: msg`Number`,
+  CHECKBOX: msg`Checkbox`,
+  RADIO: msg`Radio`,
+};
+
+export const AiFieldDetectionDialog = ({
+  open,
+  onOpenChange,
+  onComplete,
+  envelopeId,
+  teamId,
+}: AiFieldDetectionDialogProps) => {
+  const { _ } = useLingui();
+
+  const [state, setState] = useState<DialogState>('PROMPT');
+  const [messageIndex, setMessageIndex] = useState(0);
+  const [detectedFields, setDetectedFields] = useState<NormalizedFieldWithContext[]>([]);
+  const [error, setError] = useState<string | null>(null);
+  const [context, setContext] = useState('');
+  const [progress, setProgress] = useState<DetectFieldsProgressEvent | null>(null);
+
+  const onDetectClick = useCallback(async () => {
+    setState('PROCESSING');
+    setMessageIndex(0);
+    setError(null);
+    setProgress(null);
+
+    try {
+      await detectFields({
+        request: {
+          envelopeId,
+          teamId,
+          context: context || undefined,
+        },
+        onProgress: (progressEvent) => {
+          setProgress(progressEvent);
+        },
+        onComplete: (event) => {
+          setDetectedFields(event.fields);
+          setState('REVIEW');
+        },
+        onError: (err) => {
+          console.error('Detection failed:', err);
+
+          if (err.status === 429) {
+            setState('RATE_LIMITED');
+            return;
+          }
+
+          setError(err.message);
+          setState('ERROR');
+        },
+      });
+    } catch (err) {
+      console.error('Detection failed:', err);
+
+      if (err instanceof AiApiError && err.status === 429) {
+        setState('RATE_LIMITED');
+        return;
+      }
+
+      setError(err instanceof Error ? err.message : 'Failed to detect fields');
+      setState('ERROR');
+    }
+  }, [envelopeId, teamId, context]);
+
+  const onAddFields = () => {
+    onComplete(detectedFields);
+    onOpenChange(false);
+    setState('PROMPT');
+    setDetectedFields([]);
+    setContext('');
+  };
+
+  const onClose = () => {
+    onOpenChange(false);
+    setState('PROMPT');
+    setDetectedFields([]);
+    setError(null);
+    setContext('');
+    setProgress(null);
+  };
+
+  // Group fields by type for summary display
+  const fieldCountsByType = useMemo(() => {
+    const counts: Record<string, number> = {};
+
+    for (const field of detectedFields) {
+      counts[field.type] = (counts[field.type] || 0) + 1;
+    }
+
+    return Object.entries(counts).sort(([, a], [, b]) => b - a);
+  }, [detectedFields]);
+
+  useEffect(() => {
+    if (state !== 'PROCESSING') {
+      return;
+    }
+
+    const interval = setInterval(() => {
+      setMessageIndex((prev) => (prev + 1) % PROCESSING_MESSAGES.length);
+    }, 4000);
+
+    return () => clearInterval(interval);
+  }, [state]);
+
+  return (
+    <Dialog open={open}>
+      <DialogContent className="sm:max-w-lg" hideClose={true}>
+        {state === 'PROMPT' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detect fields</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="space-y-4">
+              <p className="text-sm text-muted-foreground">
+                <Trans>
+                  We'll scan your document to find form fields like signature lines, text inputs,
+                  checkboxes, and more. Detected fields will be suggested for you to review.
+                </Trans>
+              </p>
+
+              <Alert className="flex items-center gap-2 space-y-0" variant="neutral">
+                <ShieldCheckIcon className="h-5 w-5 stroke-green-600" />
+                <AlertDescription className="mt-0">
+                  <Trans>
+                    Your document is processed securely using AI services that don't retain your
+                    data.
+                  </Trans>
+                </AlertDescription>
+              </Alert>
+
+              <div className="space-y-1.5">
+                <Label htmlFor="context">
+                  <Trans>Context</Trans>
+                </Label>
+                <Textarea
+                  id="context"
+                  placeholder={_(msg`David is the Employee, Lucas is the Manager`)}
+                  value={context}
+                  onChange={(e) => setContext(e.target.value)}
+                  rows={2}
+                  className="resize-none"
+                />
+                <p className="text-xs text-muted-foreground">
+                  <Trans>Help the AI assign fields to the right recipients.</Trans>
+                </p>
+              </div>
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Skip</Trans>
+              </Button>
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Detect</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'PROCESSING' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detecting fields</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="flex flex-col items-center py-8">
+              <AnimatedDocumentScanner />
+
+              <p className="mt-8 text-muted-foreground">{_(PROCESSING_MESSAGES[messageIndex])}</p>
+
+              {progress && (
+                <p className="mt-2 text-xs text-muted-foreground/60">
+                  <Trans>
+                    Page {progress.pagesProcessed} of {progress.totalPages} -{' '}
+                    {progress.fieldsDetected} field(s) found
+                  </Trans>
+                </p>
+              )}
+
+              <p className="mt-2 max-w-[40ch] text-center text-xs text-muted-foreground/60">
+                <Trans>This can take a minute or two depending on the size of your document.</Trans>
+              </p>
+
+              <div className="mt-4 flex gap-1">
+                {PROCESSING_MESSAGES.map((_, index) => (
+                  <div
+                    key={index}
+                    className={`h-1.5 w-1.5 rounded-full transition-all duration-300 ${
+                      index === messageIndex ? 'w-4 bg-primary' : 'bg-muted-foreground/30'
+                    }`}
+                  />
+                ))}
+              </div>
+            </div>
+          </>
+        )}
+
+        {state === 'REVIEW' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detected fields</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="max-h-[400px] overflow-y-auto">
+              {detectedFields.length === 0 ? (
+                <div className="flex flex-col items-center py-8">
+                  <FormInputIcon className="h-12 w-12 text-muted-foreground/50" />
+                  <p className="mt-4 text-center text-sm text-muted-foreground">
+                    <Trans>No fields were detected in your document.</Trans>
+                  </p>
+                  <p className="mt-1 text-center text-xs text-muted-foreground/70">
+                    <Trans>You can add fields manually in the editor.</Trans>
+                  </p>
+                </div>
+              ) : (
+                <>
+                  <p className="text-sm text-muted-foreground">
+                    <Trans>We found {detectedFields.length} field(s) in your document.</Trans>
+                  </p>
+
+                  <ul className="mt-4 divide-y rounded-lg border">
+                    {fieldCountsByType.map(([type, count]) => (
+                      <li key={type} className="flex items-center justify-between px-4 py-3">
+                        <span className="text-sm">{_(FIELD_TYPE_LABELS[type]) || type}</span>
+                        <span className="text-sm font-medium text-muted-foreground">{count}</span>
+                      </li>
+                    ))}
+                  </ul>
+                </>
+              )}
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Cancel</Trans>
+              </Button>
+
+              {detectedFields.length > 0 && (
+                <Button type="button" onClick={onAddFields}>
+                  <CheckIcon className="-ml-1 mr-2 h-4 w-4" />
+                  <Trans>Add fields</Trans>
+                </Button>
+              )}
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'ERROR' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detection failed</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="py-4">
+              <p className="text-sm text-muted-foreground">
+                <Trans>Something went wrong while detecting fields.</Trans>
+              </p>
+
+              {error && <p className="mt-2 text-sm text-destructive">{error}</p>}
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Close</Trans>
+              </Button>
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Try again</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'RATE_LIMITED' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Too many requests</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="py-4">
+              <p className="text-sm text-muted-foreground">
+                <Trans>
+                  You've made too many detection requests. Please wait a minute before trying again.
+                </Trans>
+              </p>
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Close</Trans>
+              </Button>
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Try again</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+      </DialogContent>
+    </Dialog>
+  );
+};

apps/remix/app/components/dialogs/ai-recipient-detection-dialog.tsx

@@ -0,0 +1,361 @@
+import { useCallback, useEffect, useState } from 'react';
+
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
+import { CheckIcon, ShieldCheckIcon, UserIcon, XIcon } from 'lucide-react';
+
+import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
+import type { TDetectedRecipientSchema } from '@documenso/lib/server-only/ai/envelope/detect-recipients/schema';
+import { Alert, AlertDescription } from '@documenso/ui/primitives/alert';
+import { AvatarWithText } from '@documenso/ui/primitives/avatar';
+import { Button } from '@documenso/ui/primitives/button';
+import {
+  Dialog,
+  DialogContent,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '@documenso/ui/primitives/dialog';
+
+import {
+  AiApiError,
+  type DetectRecipientsProgressEvent,
+  detectRecipients,
+} from '../../../server/api/ai/detect-recipients.client';
+import { AnimatedDocumentScanner } from '../general/animated-document-scanner';
+
+type DialogState = 'PROMPT' | 'PROCESSING' | 'REVIEW' | 'ERROR' | 'RATE_LIMITED';
+
+type AiRecipientDetectionDialogProps = {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+  onComplete: (recipients: TDetectedRecipientSchema[]) => void;
+  envelopeId: string;
+  teamId: number;
+};
+
+const PROCESSING_MESSAGES = [
+  msg`Reading your document`,
+  msg`Analyzing pages`,
+  msg`Looking for signature fields`,
+  msg`Identifying recipients`,
+  msg`Extracting contact details`,
+  msg`Almost done`,
+] as const;
+
+export const AiRecipientDetectionDialog = ({
+  open,
+  onOpenChange,
+  onComplete,
+  envelopeId,
+  teamId,
+}: AiRecipientDetectionDialogProps) => {
+  const { _ } = useLingui();
+
+  const [state, setState] = useState<DialogState>('PROMPT');
+  const [messageIndex, setMessageIndex] = useState(0);
+  const [detectedRecipients, setDetectedRecipients] = useState<TDetectedRecipientSchema[]>([]);
+  const [error, setError] = useState<string | null>(null);
+  const [progress, setProgress] = useState<DetectRecipientsProgressEvent | null>(null);
+
+  const onDetectClick = useCallback(async () => {
+    setState('PROCESSING');
+    setMessageIndex(0);
+    setError(null);
+    setProgress(null);
+
+    try {
+      await detectRecipients({
+        request: {
+          envelopeId,
+          teamId,
+        },
+        onProgress: (progressEvent) => {
+          setProgress(progressEvent);
+        },
+        onComplete: (event) => {
+          setDetectedRecipients(event.recipients);
+          setState('REVIEW');
+        },
+        onError: (err) => {
+          console.error('Detection failed:', err);
+
+          if (err.status === 429) {
+            setState('RATE_LIMITED');
+            return;
+          }
+
+          setError(err.message);
+          setState('ERROR');
+        },
+      });
+    } catch (err) {
+      console.error('Detection failed:', err);
+
+      if (err instanceof AiApiError && err.status === 429) {
+        setState('RATE_LIMITED');
+        return;
+      }
+
+      setError(err instanceof Error ? err.message : 'Failed to detect recipients');
+      setState('ERROR');
+    }
+  }, [envelopeId, teamId]);
+
+  const handleRemoveRecipient = (index: number) => {
+    setDetectedRecipients((prev) => prev.filter((_, i) => i !== index));
+  };
+
+  const onAddRecipients = () => {
+    onComplete(detectedRecipients);
+    onOpenChange(false);
+    setState('PROMPT');
+    setDetectedRecipients([]);
+  };
+
+  const onClose = () => {
+    onOpenChange(false);
+    setState('PROMPT');
+    setDetectedRecipients([]);
+    setError(null);
+    setProgress(null);
+  };
+
+  useEffect(() => {
+    if (state !== 'PROCESSING') {
+      return;
+    }
+
+    const interval = setInterval(() => {
+      setMessageIndex((prev) => (prev + 1) % PROCESSING_MESSAGES.length);
+    }, 4000);
+
+    return () => clearInterval(interval);
+  }, [state]);
+
+  return (
+    <Dialog open={open}>
+      <DialogContent className="sm:max-w-lg" hideClose={true}>
+        {state === 'PROMPT' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detect recipients</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div>
+              <p className="text-sm text-muted-foreground">
+                <Trans>
+                  We'll scan your document to find signature fields and identify who needs to sign.
+                  Detected recipients will be suggested for you to review.
+                </Trans>
+              </p>
+
+              <Alert className="mt-4 flex items-center gap-2 space-y-0" variant="neutral">
+                <ShieldCheckIcon className="h-5 w-5 stroke-green-600" />
+                <AlertDescription className="mt-0">
+                  <Trans>
+                    Your document is processed securely using AI services that don't retain your
+                    data.
+                  </Trans>
+                </AlertDescription>
+              </Alert>
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Skip</Trans>
+              </Button>
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Detect</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'PROCESSING' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detecting recipients</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="flex flex-col items-center py-8">
+              <AnimatedDocumentScanner />
+
+              <p className="mt-8 text-muted-foreground">{_(PROCESSING_MESSAGES[messageIndex])}</p>
+
+              {progress && (
+                <p className="mt-2 text-xs text-muted-foreground/60">
+                  <Trans>
+                    Page {progress.pagesProcessed} of {progress.totalPages} -{' '}
+                    {progress.recipientsDetected} recipient(s) found
+                  </Trans>
+                </p>
+              )}
+
+              <p className="mt-2 max-w-[40ch] text-center text-xs text-muted-foreground/60">
+                <Trans>This can take a minute or two depending on the size of your document.</Trans>
+              </p>
+
+              <div className="mt-4 flex gap-1">
+                {PROCESSING_MESSAGES.map((_, index) => (
+                  <div
+                    key={index}
+                    className={`h-1.5 w-1.5 rounded-full transition-all duration-300 ${
+                      index === messageIndex ? 'w-4 bg-primary' : 'bg-muted-foreground/30'
+                    }`}
+                  />
+                ))}
+              </div>
+            </div>
+          </>
+        )}
+
+        {state === 'REVIEW' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detected recipients</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="max-h-[400px] overflow-y-auto">
+              {detectedRecipients.length === 0 ? (
+                <div className="flex flex-col items-center py-8">
+                  <UserIcon className="h-12 w-12 text-muted-foreground/50" />
+                  <p className="mt-4 text-center text-sm text-muted-foreground">
+                    <Trans>No recipients were detected in your document.</Trans>
+                  </p>
+                  <p className="mt-1 text-center text-xs text-muted-foreground/70">
+                    <Trans>You can add recipients manually in the editor.</Trans>
+                  </p>
+                </div>
+              ) : (
+                <>
+                  <p className="text-sm text-muted-foreground">
+                    <Trans>
+                      We found {detectedRecipients.length} recipient(s) in your document.
+                    </Trans>
+                  </p>
+
+                  <ul className="mt-4 divide-y rounded-lg border">
+                    {detectedRecipients.map((recipient, index) => (
+                      <li key={index} className="flex items-center justify-between px-4 py-3">
+                        <AvatarWithText
+                          avatarFallback={
+                            recipient.name
+                              ? recipient.name.slice(0, 1).toUpperCase()
+                              : recipient.email
+                                ? recipient.email.slice(0, 1).toUpperCase()
+                                : '?'
+                          }
+                          primaryText={
+                            <p className="text-sm font-medium text-foreground">
+                              {recipient.name || _(msg`Unknown name`)}
+                            </p>
+                          }
+                          secondaryText={
+                            <div className="text-xs text-muted-foreground">
+                              <p className="italic text-muted-foreground/70">
+                                {recipient.email || _(msg`No email detected`)}
+                              </p>
+                              <p>{_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}</p>
+                            </div>
+                          }
+                        />
+
+                        <button
+                          type="button"
+                          className="h-8 w-8 p-0 text-muted-foreground/80 hover:text-destructive focus-visible:border-destructive focus-visible:ring-destructive"
+                          onClick={() => handleRemoveRecipient(index)}
+                        >
+                          <span className="sr-only">
+                            <Trans>Remove recipient</Trans>
+                          </span>
+
+                          <XIcon className="h-4 w-4" aria-hidden="true" />
+                        </button>
+                      </li>
+                    ))}
+                  </ul>
+                </>
+              )}
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Cancel</Trans>
+              </Button>
+
+              {detectedRecipients.length > 0 && (
+                <Button type="button" onClick={onAddRecipients}>
+                  <CheckIcon className="-ml-1 mr-2 h-4 w-4" />
+                  <Trans>Add recipients</Trans>
+                </Button>
+              )}
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'ERROR' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Detection failed</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="py-4">
+              <p className="text-sm text-muted-foreground">
+                <Trans>Something went wrong while detecting recipients.</Trans>
+              </p>
+
+              {error && <p className="mt-2 text-sm text-destructive">{error}</p>}
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Close</Trans>
+              </Button>
+
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Try again</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+
+        {state === 'RATE_LIMITED' && (
+          <>
+            <DialogHeader>
+              <DialogTitle>
+                <Trans>Too many requests</Trans>
+              </DialogTitle>
+            </DialogHeader>
+
+            <div className="py-4">
+              <p className="text-sm text-muted-foreground">
+                <Trans>
+                  You've made too many detection requests. Please wait a minute before trying again.
+                </Trans>
+              </p>
+            </div>
+
+            <DialogFooter>
+              <Button type="button" variant="ghost" onClick={onClose}>
+                <Trans>Close</Trans>
+              </Button>
+              <Button type="button" onClick={onDetectClick}>
+                <Trans>Try again</Trans>
+              </Button>
+            </DialogFooter>
+          </>
+        )}
+      </DialogContent>
+    </Dialog>
+  );
+};

apps/remix/app/components/dialogs/envelope-distribute-dialog.tsx

@@ -1,4 +1,4 @@
-import { useMemo, useState } from 'react';
+import { useEffect, useMemo, useState } from 'react';
 
 import { zodResolver } from '@hookform/resolvers/zod';
 import { useLingui } from '@lingui/react/macro';
@@ -7,9 +7,7 @@ import {
   DocumentDistributionMethod,
   DocumentStatus,
   EnvelopeType,
-  type Field,
   FieldType,
-  type Recipient,
   RecipientRole,
 } from '@prisma/client';
 import { AnimatePresence, motion } from 'framer-motion';
@@ -19,8 +17,9 @@ import { useNavigate } from 'react-router';
 import { match } from 'ts-pattern';
 import * as z from 'zod';
 
+import { useCurrentEnvelopeEditor } from '@documenso/lib/client-only/providers/envelope-editor-provider';
 import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/organisation';
-import type { TEnvelope } from '@documenso/lib/types/envelope';
+import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
 import { trpc, trpc as trpcReact } from '@documenso/trpc/react';
 import { DocumentSendEmailMessageHelper } from '@documenso/ui/components/document/document-send-email-message-helper';
 import { cn } from '@documenso/ui/lib/utils';
@@ -52,16 +51,13 @@ import {
   SelectTrigger,
   SelectValue,
 } from '@documenso/ui/primitives/select';
+import { SpinnerBox } from '@documenso/ui/primitives/spinner';
 import { Tabs, TabsList, TabsTrigger } from '@documenso/ui/primitives/tabs';
 import { Textarea } from '@documenso/ui/primitives/textarea';
 import { Tooltip, TooltipContent, TooltipTrigger } from '@documenso/ui/primitives/tooltip';
 import { useToast } from '@documenso/ui/primitives/use-toast';
 
 export type EnvelopeDistributeDialogProps = {
-  envelope: Pick<TEnvelope, 'id' | 'userId' | 'teamId' | 'status' | 'type' | 'documentMeta'> & {
-    recipients: Recipient[];
-    fields: Pick<Field, 'type' | 'recipientId'>[];
-  };
   onDistribute?: () => Promise<void>;
   documentRootPath: string;
   trigger?: React.ReactNode;
@@ -86,20 +82,20 @@ export const ZEnvelopeDistributeFormSchema = z.object({
 export type TEnvelopeDistributeFormSchema = z.infer<typeof ZEnvelopeDistributeFormSchema>;
 
 export const EnvelopeDistributeDialog = ({
-  envelope,
   trigger,
   documentRootPath,
   onDistribute,
 }: EnvelopeDistributeDialogProps) => {
   const organisation = useCurrentOrganisation();
 
-  const recipients = envelope.recipients;
+  const { envelope, syncEnvelope, isAutosaving, autosaveError } = useCurrentEnvelopeEditor();
 
   const { toast } = useToast();
   const { t } = useLingui();
   const navigate = useNavigate();
 
   const [isOpen, setIsOpen] = useState(false);
+  const [isSyncing, setIsSyncing] = useState(false);
 
   const { mutateAsync: distributeEnvelope } = trpcReact.envelope.distribute.useMutation();
 
@@ -134,18 +130,43 @@ export const EnvelopeDistributeDialog = ({
 
   const distributionMethod = watch('meta.distributionMethod');
 
+  const recipientsWithIndex = useMemo(
+    () =>
+      envelope.recipients.map((recipient, index) => ({
+        ...recipient,
+        index,
+      })),
+    [envelope.recipients],
+  );
+
   const recipientsMissingSignatureFields = useMemo(
     () =>
-      envelope.recipients.filter(
+      recipientsWithIndex.filter(
         (recipient) =>
           recipient.role === RecipientRole.SIGNER &&
           !envelope.fields.some(
             (field) => field.type === FieldType.SIGNATURE && field.recipientId === recipient.id,
           ),
       ),
-    [envelope.recipients, envelope.fields],
+    [recipientsWithIndex, envelope.fields],
   );
 
+  /**
+   * List of recipients who must have an email due to having auth enabled.
+   */
+  const recipientsMissingRequiredEmail = useMemo(() => {
+    return recipientsWithIndex.filter((recipient) => {
+      const auth = extractDocumentAuthMethods({
+        documentAuth: envelope.authOptions,
+        recipientAuth: recipient.authOptions,
+      });
+
+      return (
+        (auth.recipientAccessAuthRequired || auth.recipientActionAuthRequired) && !recipient.email
+      );
+    });
+  }, [recipientsWithIndex, envelope.authOptions]);
+
   const invalidEnvelopeCode = useMemo(() => {
     if (recipientsMissingSignatureFields.length > 0) {
       return 'MISSING_SIGNATURES';
@@ -155,8 +176,12 @@ export const EnvelopeDistributeDialog = ({
       return 'MISSING_RECIPIENTS';
     }
 
+    if (recipientsMissingRequiredEmail.length > 0) {
+      return 'MISSING_REQUIRED_EMAIL';
+    }
+
     return null;
-  }, [envelope.recipients, envelope.fields, recipientsMissingSignatureFields]);
+  }, [envelope.recipients, recipientsMissingRequiredEmail, recipientsMissingSignatureFields]);
 
   const onFormSubmit = async ({ meta }: TEnvelopeDistributeFormSchema) => {
     try {
@@ -189,6 +214,29 @@ export const EnvelopeDistributeDialog = ({
     }
   };
 
+  const handleSync = async () => {
+    if (isSyncing) {
+      return;
+    }
+
+    setIsSyncing(true);
+
+    try {
+      await syncEnvelope();
+    } catch (err) {
+      console.error(err);
+    }
+
+    setIsSyncing(false);
+  };
+
+  useEffect(() => {
+    // Resync the whole envelope if the envelope is mid saving.
+    if (isOpen && (isAutosaving || autosaveError)) {
+      void handleSync();
+    }
+  }, [isOpen]);
+
   if (envelope.status !== DocumentStatus.DRAFT || envelope.type !== EnvelopeType.DOCUMENT) {
     return null;
   }
@@ -208,7 +256,7 @@ export const EnvelopeDistributeDialog = ({
           </DialogDescription>
         </DialogHeader>
 
-        {!invalidEnvelopeCode ? (
+        {!invalidEnvelopeCode || isSyncing ? (
           <Form {...form}>
             <form onSubmit={handleSubmit(onFormSubmit)}>
               <fieldset disabled={isSubmitting}>
@@ -236,7 +284,16 @@ export const EnvelopeDistributeDialog = ({
                   })}
                 >
                   <AnimatePresence initial={false} mode="wait">
-                    {distributionMethod === DocumentDistributionMethod.EMAIL && (
+                    {isSyncing ? (
+                      <motion.div
+                        key={'Flushing'}
+                        initial={{ opacity: 0, y: 5 }}
+                        animate={{ opacity: 1, y: 0, transition: { duration: 0.3 } }}
+                        exit={{ opacity: 0, transition: { duration: 0.15 } }}
+                      >
+                        <SpinnerBox spinnerProps={{ size: 'sm' }} className="h-72" />
+                      </motion.div>
+                    ) : distributionMethod === DocumentDistributionMethod.EMAIL ? (
                       <motion.div
                         key={'Emails'}
                         initial={{ opacity: 0, y: 5 }}
@@ -339,7 +396,7 @@ export const EnvelopeDistributeDialog = ({
                                       <TooltipTrigger type="button">
                                         <InfoIcon className="mx-2 h-4 w-4" />
                                       </TooltipTrigger>
-                                      <TooltipContent className="text-muted-foreground p-4">
+                                      <TooltipContent className="p-4 text-muted-foreground">
                                         <DocumentSendEmailMessageHelper />
                                       </TooltipContent>
                                     </Tooltip>
@@ -347,7 +404,7 @@ export const EnvelopeDistributeDialog = ({
 
                                   <FormControl>
                                     <Textarea
-                                      className="bg-background mt-2 h-16 resize-none"
+                                      className="mt-2 h-16 resize-none bg-background"
                                       {...field}
                                       maxLength={5000}
                                     />
@@ -359,9 +416,7 @@ export const EnvelopeDistributeDialog = ({
                           </fieldset>
                         </Form>
                       </motion.div>
-                    )}
-
-                    {distributionMethod === DocumentDistributionMethod.NONE && (
+                    ) : distributionMethod === DocumentDistributionMethod.NONE ? (
                       <motion.div
                         key={'Links'}
                         initial={{ opacity: 0, y: 5 }}
@@ -369,7 +424,7 @@ export const EnvelopeDistributeDialog = ({
                         exit={{ opacity: 0, transition: { duration: 0.15 } }}
                         className="min-h-60 rounded-lg border"
                       >
-                        <div className="text-muted-foreground py-24 text-center text-sm">
+                        <div className="py-24 text-center text-sm text-muted-foreground">
                           <p>
                             <Trans>We won't send anything to notify recipients.</Trans>
                           </p>
@@ -382,7 +437,7 @@ export const EnvelopeDistributeDialog = ({
                           </p>
                         </div>
                       </motion.div>
-                    )}
+                    ) : null}
                   </AnimatePresence>
                 </div>
 
@@ -393,7 +448,7 @@ export const EnvelopeDistributeDialog = ({
                     </Button>
                   </DialogClose>
 
-                  <Button loading={isSubmitting} type="submit">
+                  <Button loading={isSubmitting} disabled={isSyncing} type="submit">
                     {distributionMethod === DocumentDistributionMethod.EMAIL ? (
                       <Trans>Send</Trans>
                     ) : (
@@ -419,7 +474,22 @@ export const EnvelopeDistributeDialog = ({
 
                     <ul className="ml-2 mt-1 list-inside list-disc">
                       {recipientsMissingSignatureFields.map((recipient) => (
-                        <li key={recipient.id}>{recipient.email}</li>
+                        <li key={recipient.id}>
+                          {recipient.email || recipient.name || t`Recipient ${recipient.index + 1}`}
+                        </li>
+                      ))}
+                    </ul>
+                  </AlertDescription>
+                ))
+                .with('MISSING_REQUIRED_EMAIL', () => (
+                  <AlertDescription>
+                    <Trans>The following recipients require an email address:</Trans>
+
+                    <ul className="ml-2 mt-1 list-inside list-disc">
+                      {recipientsMissingRequiredEmail.map((recipient) => (
+                        <li key={recipient.id}>
+                          {recipient.email || recipient.name || t`Recipient ${recipient.index + 1}`}
+                        </li>
                       ))}
                     </ul>
                   </AlertDescription>

apps/remix/app/components/dialogs/organisation-create-dialog.tsx

@@ -367,7 +367,7 @@ const BillingPlanForm = ({
           <div className="w-full text-left">
             <div className="flex items-center justify-between">
               <p className="text-medium">
-                <Trans>Free</Trans>
+                <Trans context="Plan price">Free</Trans>
               </p>
 
               <Badge size="small" variant="neutral" className="ml-1.5">

apps/remix/app/components/dialogs/sign-field-email-dialog.tsx

@@ -24,7 +24,10 @@ import {
 import { Input } from '@documenso/ui/primitives/input';
 
 const ZSignFieldEmailFormSchema = z.object({
-  email: z.string().min(1, { message: msg`Email is required`.id }),
+  email: z
+    .string()
+    .email()
+    .min(1, { message: msg`Email is required`.id }),
 });
 
 type TSignFieldEmailFormSchema = z.infer<typeof ZSignFieldEmailFormSchema>;

apps/remix/app/components/dialogs/template-bulk-send-dialog.tsx

@@ -103,8 +103,8 @@ export const TemplateBulkSendDialog = ({
       console.error(err);
 
       toast({
-        title: 'Error',
-        description: 'Failed to upload CSV. Please check the file format and try again.',
+        title: _(msg`Error`),
+        description: _(msg`Failed to upload CSV. Please check the file format and try again.`),
         variant: 'destructive',
       });
     }

apps/remix/app/components/dialogs/template-use-dialog.tsx

@@ -21,6 +21,7 @@ import {
   SKIP_QUERY_BATCH_META,
 } from '@documenso/lib/constants/trpc';
 import { AppError } from '@documenso/lib/errors/app-error';
+import { ZRecipientEmailSchema } from '@documenso/lib/types/recipient';
 import { putPdfFile } from '@documenso/lib/universal/upload/put-file';
 import { trpc } from '@documenso/trpc/react';
 import { cn } from '@documenso/ui/lib/utils';
@@ -65,7 +66,7 @@ const ZAddRecipientsForNewDocumentSchema = z.object({
   recipients: z.array(
     z.object({
       id: z.number(),
-      email: z.string().email(),
+      email: ZRecipientEmailSchema,
       name: z.string(),
       signingOrder: z.number().optional(),
     }),
@@ -100,12 +101,29 @@ export function TemplateUseDialog({
 
   const [open, setOpen] = useState(false);
 
-  const form = useForm<TAddRecipientsForNewDocumentSchema>({
-    resolver: zodResolver(ZAddRecipientsForNewDocumentSchema),
-    defaultValues: {
+  const { data: response, isLoading: isLoadingEnvelopeItems } = trpc.envelope.item.getMany.useQuery(
+    {
+      envelopeId,
+    },
+    {
+      placeholderData: (previousData) => previousData,
+      ...SKIP_QUERY_BATCH_META,
+      ...DO_NOT_INVALIDATE_QUERY_ON_MUTATION,
+      enabled: open,
+    },
+  );
+
+  const envelopeItems = response?.data ?? [];
+
+  const generateDefaultFormValues = () => {
+    return {
       distributeDocument: false,
       useCustomDocument: false,
-      customDocumentData: [],
+      customDocumentData: envelopeItems.map((item) => ({
+        title: item.title,
+        data: undefined,
+        envelopeItemId: item.id,
+      })),
       recipients: recipients
         .sort((a, b) => (a.signingOrder || 0) - (b.signingOrder || 0))
         .map((recipient) => {
@@ -124,7 +142,12 @@ export function TemplateUseDialog({
             signingOrder: recipient.signingOrder ?? undefined,
           };
         }),
-    },
+    };
+  };
+
+  const form = useForm<TAddRecipientsForNewDocumentSchema>({
+    resolver: zodResolver(ZAddRecipientsForNewDocumentSchema),
+    defaultValues: generateDefaultFormValues(),
   });
 
   const { replace, fields: localCustomDocumentData } = useFieldArray({
@@ -132,19 +155,6 @@ export function TemplateUseDialog({
     name: 'customDocumentData',
   });
 
-  const { data: response, isLoading: isLoadingEnvelopeItems } = trpc.envelope.item.getMany.useQuery(
-    {
-      envelopeId,
-    },
-    {
-      placeholderData: (previousData) => previousData,
-      ...SKIP_QUERY_BATCH_META,
-      ...DO_NOT_INVALIDATE_QUERY_ON_MUTATION,
-    },
-  );
-
-  const envelopeItems = response?.data ?? [];
-
   const { mutateAsync: createDocumentFromTemplate } =
     trpc.template.createDocumentFromTemplate.useMutation();
 
@@ -214,8 +224,8 @@ export function TemplateUseDialog({
   });
 
   useEffect(() => {
-    if (!open) {
-      form.reset();
+    if (open) {
+      form.reset(generateDefaultFormValues());
     }
   }, [open, form]);
 
@@ -322,7 +332,7 @@ export function TemplateUseDialog({
                             <Input
                               {...field}
                               aria-label="Name"
-                              placeholder={recipients[index].name || _(msg`Name`)}
+                              placeholder={recipients[index].name || _(msg`Recipient ${index + 1}`)}
                             />
                           </FormControl>
                           <FormMessage />
@@ -349,7 +359,7 @@ export function TemplateUseDialog({
 
                             {documentDistributionMethod === DocumentDistributionMethod.EMAIL && (
                               <label
-                                className="text-muted-foreground ml-2 flex items-center text-sm"
+                                className="ml-2 flex items-center text-sm text-muted-foreground"
                                 htmlFor="distributeDocument"
                               >
                                 <Trans>Send document</Trans>
@@ -358,7 +368,7 @@ export function TemplateUseDialog({
                                     <InfoIcon className="mx-1 h-4 w-4" />
                                   </TooltipTrigger>
 
-                                  <TooltipContent className="text-muted-foreground z-[99999] max-w-md space-y-2 p-4">
+                                  <TooltipContent className="z-[99999] max-w-md space-y-2 p-4 text-muted-foreground">
                                     <p>
                                       <Trans>
                                         The document will be immediately sent to recipients if this
@@ -378,7 +388,7 @@ export function TemplateUseDialog({
 
                             {documentDistributionMethod === DocumentDistributionMethod.NONE && (
                               <label
-                                className="text-muted-foreground ml-2 flex items-center text-sm"
+                                className="ml-2 flex items-center text-sm text-muted-foreground"
                                 htmlFor="distributeDocument"
                               >
                                 <Trans>Create as pending</Trans>
@@ -386,7 +396,7 @@ export function TemplateUseDialog({
                                   <TooltipTrigger type="button">
                                     <InfoIcon className="mx-1 h-4 w-4" />
                                   </TooltipTrigger>
-                                  <TooltipContent className="text-muted-foreground z-[99999] max-w-md space-y-2 p-4">
+                                  <TooltipContent className="z-[99999] max-w-md space-y-2 p-4 text-muted-foreground">
                                     <p>
                                       <Trans>
                                         Create the document as pending and ready to sign.
@@ -432,7 +442,7 @@ export function TemplateUseDialog({
                           }}
                         />
                         <label
-                          className="text-muted-foreground ml-2 flex items-center text-sm"
+                          className="ml-2 flex items-center text-sm text-muted-foreground"
                           htmlFor="useCustomDocument"
                         >
                           <Trans>Upload custom document</Trans>
@@ -440,7 +450,7 @@ export function TemplateUseDialog({
                             <TooltipTrigger type="button">
                               <InfoIcon className="mx-1 h-4 w-4" />
                             </TooltipTrigger>
-                            <TooltipContent className="text-muted-foreground z-[99999] max-w-md space-y-2 p-4">
+                            <TooltipContent className="z-[99999] max-w-md space-y-2 p-4 text-muted-foreground">
                               <p>
                                 <Trans>
                                   Upload a custom document to use instead of the template's default
@@ -470,19 +480,19 @@ export function TemplateUseDialog({
                               <FormControl>
                                 <div
                                   key={item.id}
-                                  className="border-border bg-card hover:bg-accent/10 flex items-center gap-4 rounded-lg border p-4 transition-colors"
+                                  className="flex items-center gap-4 rounded-lg border border-border bg-card p-4 transition-colors hover:bg-accent/10"
                                 >
                                   <div className="flex-shrink-0">
-                                    <div className="bg-primary/10 flex h-10 w-10 items-center justify-center rounded-lg">
-                                      <FileTextIcon className="text-primary h-5 w-5" />
+                                    <div className="flex h-10 w-10 items-center justify-center rounded-lg bg-primary/10">
+                                      <FileTextIcon className="h-5 w-5 text-primary" />
                                     </div>
                                   </div>
 
                                   <div className="min-w-0 flex-1">
-                                    <h4 className="text-foreground truncate text-sm font-medium">
+                                    <h4 className="truncate text-sm font-medium text-foreground">
                                       {item.title}
                                     </h4>
-                                    <p className="text-muted-foreground mt-0.5 text-xs">
+                                    <p className="mt-0.5 text-xs text-muted-foreground">
                                       {field.value ? (
                                         <div>
                                           <Trans>

apps/remix/app/components/embed/authoring/configure-document-view.types.ts

@@ -5,6 +5,7 @@ import {
   ZDocumentMetaDateFormatSchema,
   ZDocumentMetaLanguageSchema,
 } from '@documenso/lib/types/document-meta';
+import { ZRecipientEmailSchema } from '@documenso/lib/types/recipient';
 import { DocumentDistributionMethod } from '@documenso/prisma/generated/types';
 
 // Define the schema for configuration
@@ -55,7 +56,7 @@ export const ZConfigureTemplateEmbedFormSchema = ZConfigureEmbedFormSchema.exten
       nativeId: z.number().optional(),
       formId: z.string(),
       name: z.string(),
-      email: z.union([z.string().length(0), z.string().email('Invalid email address')]),
+      email: ZRecipientEmailSchema,
       role: z.enum(['SIGNER', 'CC', 'APPROVER', 'VIEWER', 'ASSISTANT']),
       signingOrder: z.number().optional(),
       disabled: z.boolean().optional(),

apps/remix/app/components/embed/authoring/configure-fields-view.tsx

@@ -1,5 +1,6 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 
+import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
 import type { EnvelopeItem, FieldType } from '@prisma/client';
@@ -229,8 +230,8 @@ export const ConfigureFieldsView = ({
         setFieldClipboard(lastActiveField);
 
         toast({
-          title: 'Copied field',
-          description: 'Copied field to clipboard',
+          title: _(msg`Copied field`),
+          description: _(msg`Copied field to clipboard`),
         });
       }
     },

apps/remix/app/components/embed/multisign/multi-sign-document-signing-view.tsx

@@ -150,8 +150,8 @@ export const MultiSignDocumentSigningView = ({
       onDocumentError?.();
 
       toast({
-        title: 'Error',
-        description: 'Failed to complete the document. Please try again.',
+        title: _(msg`Error`),
+        description: _(msg`Failed to complete the document. Please try again.`),
         variant: 'destructive',
       });
     } finally {

apps/remix/app/components/forms/document-preferences-form.tsx

@@ -58,6 +58,7 @@ export type TDocumentPreferencesFormSchema = {
   includeSigningCertificate: boolean | null;
   includeAuditLog: boolean | null;
   signatureTypes: DocumentSignatureType[];
+  aiFeaturesEnabled: boolean | null;
 };
 
 type SettingsSubset = Pick<
@@ -72,11 +73,13 @@ type SettingsSubset = Pick<
   | 'typedSignatureEnabled'
   | 'uploadSignatureEnabled'
   | 'drawSignatureEnabled'
+  | 'aiFeaturesEnabled'
 >;
 
 export type DocumentPreferencesFormProps = {
   settings: SettingsSubset;
   canInherit: boolean;
+  isAiFeaturesConfigured?: boolean;
   onFormSubmit: (data: TDocumentPreferencesFormSchema) => Promise<void>;
 };
 
@@ -84,6 +87,7 @@ export const DocumentPreferencesForm = ({
   settings,
   onFormSubmit,
   canInherit,
+  isAiFeaturesConfigured = false,
 }: DocumentPreferencesFormProps) => {
   const { t } = useLingui();
   const { user, organisations } = useSession();
@@ -105,6 +109,7 @@ export const DocumentPreferencesForm = ({
     signatureTypes: z.array(z.nativeEnum(DocumentSignatureType)).min(canInherit ? 0 : 1, {
       message: msg`At least one signature type must be enabled`.id,
     }),
+    aiFeaturesEnabled: z.boolean().nullable(),
   });
 
   const form = useForm<TDocumentPreferencesFormSchema>({
@@ -120,6 +125,7 @@ export const DocumentPreferencesForm = ({
       includeSigningCertificate: settings.includeSigningCertificate,
       includeAuditLog: settings.includeAuditLog,
       signatureTypes: extractTeamSignatureSettings({ ...settings }),
+      aiFeaturesEnabled: settings.aiFeaturesEnabled,
     },
     resolver: zodResolver(ZDocumentPreferencesFormSchema),
   });
@@ -312,7 +318,7 @@ export const DocumentPreferencesForm = ({
                     }))}
                     selectedValues={field.value}
                     onChange={field.onChange}
-                    className="bg-background w-full"
+                    className="w-full bg-background"
                     enableSearch={false}
                     emptySelectionPlaceholder={
                       canInherit ? t`Inherit from organisation` : t`Select signature types`
@@ -378,7 +384,7 @@ export const DocumentPreferencesForm = ({
                   </FormControl>
 
                   <div className="pt-2">
-                    <div className="text-muted-foreground text-xs font-medium">
+                    <div className="text-xs font-medium text-muted-foreground">
                       <Trans>Preview</Trans>
                     </div>
 
@@ -509,6 +515,59 @@ export const DocumentPreferencesForm = ({
             )}
           />
 
+          {isAiFeaturesConfigured && (
+            <FormField
+              control={form.control}
+              name="aiFeaturesEnabled"
+              render={({ field }) => (
+                <FormItem className="flex-1">
+                  <FormLabel>
+                    <Trans>AI Features</Trans>
+                  </FormLabel>
+
+                  <FormControl>
+                    <Select
+                      {...field}
+                      value={field.value === null ? '-1' : field.value.toString()}
+                      onValueChange={(value) =>
+                        field.onChange(value === 'true' ? true : value === 'false' ? false : null)
+                      }
+                    >
+                      <SelectTrigger className="bg-background text-muted-foreground">
+                        <SelectValue />
+                      </SelectTrigger>
+
+                      <SelectContent>
+                        <SelectItem value="true">
+                          <Trans>Enabled</Trans>
+                        </SelectItem>
+
+                        <SelectItem value="false">
+                          <Trans>Disabled</Trans>
+                        </SelectItem>
+
+                        {canInherit && (
+                          <SelectItem value={'-1'}>
+                            <Trans>Inherit from organisation</Trans>
+                          </SelectItem>
+                        )}
+                      </SelectContent>
+                    </Select>
+                  </FormControl>
+
+                  <FormDescription>
+                    <Trans>
+                      Enable AI-powered features such as automatic recipient detection. When
+                      enabled, document content will be sent to AI providers. We only use providers
+                      that do not retain data for training and prefer European regions where
+                      available.
+                    </Trans>
+                  </FormDescription>
+                </FormItem>
+              )}
+            />
+          )}
+
           <div className="flex flex-row justify-end space-x-4">
             <Button type="submit" loading={form.formState.isSubmitting}>
               <Trans>Update</Trans>

apps/remix/app/components/forms/signin.tsx

@@ -201,7 +201,7 @@ export const SignInForm = ({
         .otherwise(() => handleFallbackErrorMessages(error.code));
 
       toast({
-        title: 'Something went wrong',
+        title: _(msg`Something went wrong`),
         description: _(errorMessage),
         duration: 10000,
         variant: 'destructive',

apps/remix/app/components/general/animated-document-scanner.tsx

@@ -0,0 +1,78 @@
+import { useEffect, useState } from 'react';
+
+import { SearchIcon } from 'lucide-react';
+
+import { cn } from '@documenso/ui/lib/utils';
+
+export type AnimatedDocumentScannerProps = {
+  className?: string;
+  interval?: number;
+};
+
+export const AnimatedDocumentScanner = ({
+  className,
+  interval = 2500,
+}: AnimatedDocumentScannerProps) => {
+  const [magPosition, setMagPosition] = useState({ x: 0, y: 0, page: 0 });
+
+  useEffect(() => {
+    const moveInterval = setInterval(() => {
+      setMagPosition({
+        x: Math.random() * 60 - 30,
+        y: Math.random() * 50 - 25,
+        page: Math.random() > 0.5 ? 1 : 0,
+      });
+    }, interval);
+
+    return () => clearInterval(moveInterval);
+  }, [interval]);
+
+  return (
+    <div className={cn('relative mx-auto h-36 w-56', className)}>
+      {/* Magnifying glass */}
+      <div
+        className="pointer-events-none absolute z-50 transition-all duration-1000 ease-in-out"
+        style={{
+          left: magPosition.page === 0 ? '25%' : '75%',
+          top: '50%',
+          transform: `translate(calc(-50% + ${magPosition.x}px), calc(-50% + ${magPosition.y}px))`,
+        }}
+      >
+        <SearchIcon className="h-8 w-8 text-foreground" />
+      </div>
+
+      {/* Book container */}
+      <div className="relative h-full w-full animate-pulse" style={{ perspective: '800px' }}>
+        <div className="relative h-full w-full" style={{ transformStyle: 'preserve-3d' }}>
+          {/* Left page */}
+          <div
+            className="absolute left-0 top-0 h-full w-[calc(50%)] origin-right overflow-hidden rounded-l-md border border-border bg-card shadow-md"
+            style={{ transform: 'rotateY(15deg) skewY(-1deg)' }}
+          >
+            <div className="absolute inset-3 space-y-2">
+              <div className="h-1.5 w-3/4 rounded-sm bg-muted" />
+              <div className="h-1.5 w-full rounded-sm bg-muted" />
+              <div className="h-1.5 w-5/6 rounded-sm bg-muted" />
+              <div className="h-1.5 w-2/3 rounded-sm bg-muted" />
+              <div className="mt-3 h-6 w-3/4 rounded border border-dashed border-primary" />
+            </div>
+          </div>
+
+          {/* Right page */}
+          <div
+            className="absolute right-0 top-0 h-full w-[calc(50%)] origin-left overflow-hidden rounded-r-md border border-border bg-card shadow-md"
+            style={{ transform: 'rotateY(-15deg) skewY(1deg)' }}
+          >
+            <div className="absolute inset-3 space-y-2">
+              <div className="h-1.5 w-full rounded-sm bg-muted" />
+              <div className="h-1.5 w-4/5 rounded-sm bg-muted" />
+              <div className="h-1.5 w-full rounded-sm bg-muted" />
+              <div className="h-1.5 w-3/5 rounded-sm bg-muted" />
+              <div className="mt-3 h-6 w-2/3 rounded border border-dashed border-primary" />
+            </div>
+          </div>
+        </div>
+      </div>
+    </div>
+  );
+};

apps/remix/app/components/general/avatar-with-recipient.tsx

@@ -56,13 +56,13 @@ export function AvatarWithRecipient({ recipient, documentStatus }: AvatarWithRec
       />
 
       <div
-        className="text-muted-foreground text-sm"
+        className="text-sm text-muted-foreground"
         title={
           signingToken ? _(msg`Click to copy signing link for sending to recipient`) : undefined
         }
       >
-        <p>{recipient.email}</p>
-        <p className="text-muted-foreground/70 text-xs">
+        <p>{recipient.email || recipient.name}</p>
+        <p className="text-xs text-muted-foreground/70">
           {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
         </p>
       </div>

apps/remix/app/components/general/document-signing/document-signing-complete-dialog.tsx

@@ -57,12 +57,13 @@ export type DocumentSigningCompleteDialogProps = {
     name: string;
     email: string;
   };
-  directTemplatePayload?: {
+  recipientPayload?: {
     name: string;
     email: string;
   };
   buttonSize?: 'sm' | 'lg';
   position?: 'start' | 'end' | 'center';
+  disableNameInput?: boolean;
 };
 
 const ZNextSignerFormSchema = z.object({
@@ -89,10 +90,11 @@ export const DocumentSigningCompleteDialog = ({
   recipient,
   disabled = false,
   allowDictateNextSigner = false,
-  directTemplatePayload,
+  recipientPayload,
   defaultNextSigner,
   buttonSize = 'lg',
   position,
+  disableNameInput = false,
 }: DocumentSigningCompleteDialogProps) => {
   const { t } = useLingui();
 
@@ -113,11 +115,11 @@ export const DocumentSigningCompleteDialog = ({
     },
   });
 
-  const directRecipientForm = useForm<TDirectRecipientFormSchema>({
+  const recipientForm = useForm<TDirectRecipientFormSchema>({
     resolver: zodResolver(ZDirectRecipientFormSchema),
     defaultValues: {
-      name: directTemplatePayload?.name ?? '',
-      email: directTemplatePayload?.email ?? '',
+      name: recipientPayload?.name ?? '',
+      email: recipientPayload?.email ?? '',
     },
   });
 
@@ -145,16 +147,16 @@ export const DocumentSigningCompleteDialog = ({
 
   const onFormSubmit = async (data: TNextSignerFormSchema) => {
     try {
-      let directRecipient: { name: string; email: string } | undefined;
+      let recipientOverridePayload: { name: string; email: string } | undefined;
 
-      if (directTemplatePayload && !directTemplatePayload.email) {
-        const isFormValid = await directRecipientForm.trigger();
+      if (recipientPayload && !recipientPayload.email) {
+        const isFormValid = await recipientForm.trigger();
 
         if (!isFormValid) {
           return;
         }
 
-        directRecipient = directRecipientForm.getValues();
+        recipientOverridePayload = recipientForm.getValues();
       }
 
       // Check if 2FA is required
@@ -168,7 +170,7 @@ export const DocumentSigningCompleteDialog = ({
           ? { name: data.name, email: data.email }
           : undefined;
 
-      await onSignatureComplete(nextSigner, data.accessAuthOptions, directRecipient);
+      await onSignatureComplete(nextSigner, data.accessAuthOptions, recipientOverridePayload);
     } catch (error) {
       const err = AppError.parseError(error);
 
@@ -222,7 +224,7 @@ export const DocumentSigningCompleteDialog = ({
             <Trans>Are you sure?</Trans>
           </DialogTitle>
           <DialogDescription>
-            <div className="text-muted-foreground max-w-[50ch]">
+            <div className="max-w-[50ch] text-muted-foreground">
               {match(recipient.role)
                 .with(RecipientRole.VIEWER, () => (
                   <span className="inline-flex flex-wrap">
@@ -250,19 +252,19 @@ export const DocumentSigningCompleteDialog = ({
           </DialogDescription>
         </DialogHeader>
 
-        <div className="border-border bg-muted/50 rounded-lg border p-4 text-center">
-          <p className="text-muted-foreground text-sm font-medium">{documentTitle}</p>
+        <div className="rounded-lg border border-border bg-muted/50 p-4 text-center">
+          <p className="text-sm font-medium text-muted-foreground">{documentTitle}</p>
         </div>
 
         {!showTwoFactorForm && (
           <>
             <fieldset disabled={form.formState.isSubmitting} className="border-none p-0">
-              {directTemplatePayload && !directTemplatePayload.email && (
-                <Form {...directRecipientForm}>
+              {recipientPayload && !recipientPayload.email && (
+                <Form {...recipientForm}>
                   <div className="mb-4 flex flex-col gap-4">
                     <div className="flex flex-col gap-4 md:flex-row">
                       <FormField
-                        control={directRecipientForm.control}
+                        control={recipientForm.control}
                         name="name"
                         render={({ field }) => (
                           <FormItem className="flex-1">
@@ -274,7 +276,7 @@ export const DocumentSigningCompleteDialog = ({
                                 {...field}
                                 className="mt-2"
                                 placeholder={t`Enter your name`}
-                                disabled={isNameLocked}
+                                disabled={isNameLocked || disableNameInput}
                               />
                             </FormControl>
 
@@ -284,7 +286,7 @@ export const DocumentSigningCompleteDialog = ({
                       />
 
                       <FormField
-                        control={directRecipientForm.control}
+                        control={recipientForm.control}
                         name="email"
                         render={({ field }) => (
                           <FormItem className="flex-1">

apps/remix/app/components/general/document-signing/document-signing-form.tsx

@@ -108,8 +108,8 @@ export const DocumentSigningForm = ({
       await completeDocument({ nextSigner });
     } catch (err) {
       toast({
-        title: 'Error',
-        description: 'An error occurred while completing the document. Please try again.',
+        title: _(msg`Error`),
+        description: _(msg`An error occurred while completing the document. Please try again.`),
         variant: 'destructive',
       });
 

apps/remix/app/components/general/document-signing/document-signing-page-view-v1.tsx

@@ -187,45 +187,74 @@ export const DocumentSigningPageViewV1 = ({
 
         <div className="mt-1.5 flex flex-wrap items-center justify-between gap-y-2 sm:mt-2.5 sm:gap-y-0">
           <div className="max-w-[50ch]">
-            <span className="truncate text-muted-foreground" title={senderName}>
-              {senderName} {senderEmail}
-            </span>{' '}
             <span className="text-muted-foreground">
               {match(recipient.role)
                 .with(RecipientRole.VIEWER, () =>
                   includeSenderDetails ? (
                     <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
                       on behalf of "{document.team?.name}" has invited you to view this document
                     </Trans>
                   ) : (
-                    <Trans>has invited you to view this document</Trans>
+                    <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
+                      has invited you to view this document
+                    </Trans>
                   ),
                 )
                 .with(RecipientRole.SIGNER, () =>
                   includeSenderDetails ? (
                     <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
                       on behalf of "{document.team?.name}" has invited you to sign this document
                     </Trans>
                   ) : (
-                    <Trans>has invited you to sign this document</Trans>
+                    <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
+                      has invited you to sign this document
+                    </Trans>
                   ),
                 )
                 .with(RecipientRole.APPROVER, () =>
                   includeSenderDetails ? (
                     <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
                       on behalf of "{document.team?.name}" has invited you to approve this document
                     </Trans>
                   ) : (
-                    <Trans>has invited you to approve this document</Trans>
+                    <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
+                      has invited you to approve this document
+                    </Trans>
                   ),
                 )
                 .with(RecipientRole.ASSISTANT, () =>
                   includeSenderDetails ? (
                     <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
                       on behalf of "{document.team?.name}" has invited you to assist this document
                     </Trans>
                   ) : (
-                    <Trans>has invited you to assist this document</Trans>
+                    <Trans>
+                      <span className="truncate" title={senderName}>
+                        {senderName} {senderEmail}
+                      </span>{' '}
+                      has invited you to assist this document
+                    </Trans>
                   ),
                 )
                 .otherwise(() => null)}

apps/remix/app/components/general/document-signing/document-signing-reject-dialog.tsx

@@ -74,8 +74,8 @@ export function DocumentSigningRejectDialog({
       });
 
       toast({
-        title: 'Document rejected',
-        description: 'The document has been successfully rejected.',
+        title: t`Document rejected`,
+        description: t`The document has been successfully rejected.`,
         duration: 5000,
       });
 
@@ -88,8 +88,8 @@ export function DocumentSigningRejectDialog({
       }
     } catch (err) {
       toast({
-        title: 'Error',
-        description: 'An error occurred while rejecting the document. Please try again.',
+        title: t`Error`,
+        description: t`An error occurred while rejecting the document. Please try again.`,
         variant: 'destructive',
         duration: 5000,
       });

apps/remix/app/components/general/envelope-editor/envelope-editor-fields-page.tsx

@@ -1,28 +1,31 @@
-import { lazy, useEffect, useMemo } from 'react';
+import { lazy, useEffect, useMemo, useState } from 'react';
 
 import type { MessageDescriptor } from '@lingui/core';
 import { msg } from '@lingui/core/macro';
-import { Trans, useLingui } from '@lingui/react/macro';
-import { FieldType, RecipientRole } from '@prisma/client';
-import { FileTextIcon } from 'lucide-react';
+import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
+import { DocumentStatus, FieldType, RecipientRole } from '@prisma/client';
+import { FileTextIcon, SparklesIcon } from 'lucide-react';
 import { Link, useSearchParams } from 'react-router';
 import { isDeepEqual } from 'remeda';
 import { match } from 'ts-pattern';
 
 import { useCurrentEnvelopeEditor } from '@documenso/lib/client-only/providers/envelope-editor-provider';
 import { useCurrentEnvelopeRender } from '@documenso/lib/client-only/providers/envelope-render-provider';
-import type {
-  TCheckboxFieldMeta,
-  TDateFieldMeta,
-  TDropdownFieldMeta,
-  TEmailFieldMeta,
-  TFieldMetaSchema,
-  TInitialsFieldMeta,
-  TNameFieldMeta,
-  TNumberFieldMeta,
-  TRadioFieldMeta,
-  TSignatureFieldMeta,
-  TTextFieldMeta,
+import type { NormalizedFieldWithContext } from '@documenso/lib/server-only/ai/envelope/detect-fields/types';
+import {
+  FIELD_META_DEFAULT_VALUES,
+  type TCheckboxFieldMeta,
+  type TDateFieldMeta,
+  type TDropdownFieldMeta,
+  type TEmailFieldMeta,
+  type TFieldMetaSchema,
+  type TInitialsFieldMeta,
+  type TNameFieldMeta,
+  type TNumberFieldMeta,
+  type TRadioFieldMeta,
+  type TSignatureFieldMeta,
+  type TTextFieldMeta,
 } from '@documenso/lib/types/field-meta';
 import { canRecipientFieldsBeModified } from '@documenso/lib/utils/recipients';
 import { AnimateGenericFadeInOut } from '@documenso/ui/components/animate/animate-generic-fade-in-out';
@@ -31,6 +34,7 @@ import { Alert, AlertDescription, AlertTitle } from '@documenso/ui/primitives/al
 import { Button } from '@documenso/ui/primitives/button';
 import { Separator } from '@documenso/ui/primitives/separator';
 
+import { AiFieldDetectionDialog } from '~/components/dialogs/ai-field-detection-dialog';
 import { EditorFieldCheckboxForm } from '~/components/forms/editor/editor-field-checkbox-form';
 import { EditorFieldDateForm } from '~/components/forms/editor/editor-field-date-form';
 import { EditorFieldDropdownForm } from '~/components/forms/editor/editor-field-dropdown-form';
@@ -41,6 +45,7 @@ import { EditorFieldNumberForm } from '~/components/forms/editor/editor-field-nu
 import { EditorFieldRadioForm } from '~/components/forms/editor/editor-field-radio-form';
 import { EditorFieldSignatureForm } from '~/components/forms/editor/editor-field-signature-form';
 import { EditorFieldTextForm } from '~/components/forms/editor/editor-field-text-form';
+import { useCurrentTeam } from '~/providers/team';
 
 import { EnvelopeEditorFieldDragDrop } from './envelope-editor-fields-drag-drop';
 import { EnvelopeRendererFileSelector } from './envelope-file-selector';
@@ -67,11 +72,15 @@ const FieldSettingsTypeTranslations: Record<FieldType, MessageDescriptor> = {
 export const EnvelopeEditorFieldsPage = () => {
   const [searchParams] = useSearchParams();
 
+  const team = useCurrentTeam();
+
   const { envelope, editorFields, relativePath } = useCurrentEnvelopeEditor();
 
   const { currentEnvelopeItem } = useCurrentEnvelopeRender();
 
-  const { t } = useLingui();
+  const { _ } = useLingui();
+
+  const [isAiFieldDialogOpen, setIsAiFieldDialogOpen] = useState(false);
 
   const selectedField = useMemo(
     () => structuredClone(editorFields.selectedField),
@@ -96,6 +105,24 @@ export const EnvelopeEditorFieldsPage = () => {
     }
   };
 
+  const onFieldDetectionComplete = (fields: NormalizedFieldWithContext[]) => {
+    for (const field of fields) {
+      editorFields.addField({
+        height: field.height,
+        width: field.width,
+        positionX: field.positionX,
+        positionY: field.positionY,
+        type: field.type,
+        envelopeItemId: field.envelopeItemId,
+        recipientId: field.recipientId,
+        page: field.pageNumber,
+        fieldMeta: structuredClone(FIELD_META_DEFAULT_VALUES[field.type]),
+      });
+    }
+
+    setIsAiFieldDialogOpen(false);
+  };
+
   /**
    * Set the selected recipient to the first recipient in the envelope.
    */
@@ -202,6 +229,35 @@ export const EnvelopeEditorFieldsPage = () => {
               selectedRecipientId={editorFields.selectedRecipient?.id ?? null}
               selectedEnvelopeItemId={currentEnvelopeItem?.id ?? null}
             />
+
+            {team.preferences.aiFeaturesEnabled && (
+              <>
+                <Button
+                  type="button"
+                  variant="outline"
+                  size="sm"
+                  className="mt-4 w-full"
+                  onClick={() => setIsAiFieldDialogOpen(true)}
+                  disabled={envelope.status !== DocumentStatus.DRAFT}
+                  title={
+                    envelope.status !== DocumentStatus.DRAFT
+                      ? _(msg`You can only detect fields in draft envelopes`)
+                      : undefined
+                  }
+                >
+                  <SparklesIcon className="-ml-1 mr-2 h-4 w-4" />
+                  <Trans>Detect with AI</Trans>
+                </Button>
+
+                <AiFieldDetectionDialog
+                  open={isAiFieldDialogOpen}
+                  onOpenChange={setIsAiFieldDialogOpen}
+                  onComplete={onFieldDetectionComplete}
+                  envelopeId={envelope.id}
+                  teamId={envelope.teamId}
+                />
+              </>
+            )}
           </section>
 
           {/* Field details section. */}
@@ -243,7 +299,7 @@ export const EnvelopeEditorFieldsPage = () => {
 
                 <div className="px-4 [&_label]:text-xs [&_label]:text-foreground/70">
                   <h3 className="text-sm font-semibold">
-                    {t(FieldSettingsTypeTranslations[selectedField.type])}
+                    {_(FieldSettingsTypeTranslations[selectedField.type])}
                   </h3>
 
                   {match(selectedField.type)

apps/remix/app/components/general/envelope-editor/envelope-editor-header.tsx

@@ -30,18 +30,11 @@ import { EnvelopeItemTitleInput } from './envelope-editor-title-input';
 export default function EnvelopeEditorHeader() {
   const { t } = useLingui();
 
-  const {
-    envelope,
-    isDocument,
-    isTemplate,
-    updateEnvelope,
-    autosaveError,
-    relativePath,
-    editorFields,
-  } = useCurrentEnvelopeEditor();
+  const { envelope, isDocument, isTemplate, updateEnvelope, autosaveError, relativePath } =
+    useCurrentEnvelopeEditor();
 
   return (
-    <nav className="bg-background border-border w-full border-b px-4 py-3 md:px-6">
+    <nav className="w-full border-b border-border bg-background px-4 py-3 md:px-6">
       <div className="flex items-center justify-between">
         <div className="flex items-center space-x-4">
           <Link to="/">
@@ -147,10 +140,6 @@ export default function EnvelopeEditorHeader() {
           {isDocument && (
             <>
               <EnvelopeDistributeDialog
-                envelope={{
-                  ...envelope,
-                  fields: editorFields.localFields,
-                }}
                 documentRootPath={relativePath.documentRootPath}
                 trigger={
                   <Button size="sm">

apps/remix/app/components/general/envelope-editor/envelope-editor-recipient-form.tsx

@@ -8,12 +8,12 @@ import {
   type SensorAPI,
 } from '@hello-pangea/dnd';
 import { zodResolver } from '@hookform/resolvers/zod';
-import { msg } from '@lingui/core/macro';
 import { Trans, useLingui } from '@lingui/react/macro';
 import { DocumentSigningOrder, EnvelopeType, RecipientRole, SendStatus } from '@prisma/client';
 import { motion } from 'framer-motion';
-import { GripVerticalIcon, HelpCircleIcon, PlusIcon, TrashIcon } from 'lucide-react';
+import { GripVerticalIcon, HelpCircleIcon, PlusIcon, SparklesIcon, TrashIcon } from 'lucide-react';
 import { useFieldArray, useForm, useWatch } from 'react-hook-form';
+import { useSearchParams } from 'react-router';
 import { isDeepEqual, prop, sortBy } from 'remeda';
 import { z } from 'zod';
 
@@ -22,10 +22,12 @@ import { useDebouncedValue } from '@documenso/lib/client-only/hooks/use-debounce
 import { useCurrentEnvelopeEditor } from '@documenso/lib/client-only/providers/envelope-editor-provider';
 import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/organisation';
 import { useSession } from '@documenso/lib/client-only/providers/session';
+import type { TDetectedRecipientSchema } from '@documenso/lib/server-only/ai/envelope/detect-recipients/schema';
 import {
   ZRecipientActionAuthTypesSchema,
   ZRecipientAuthOptionsSchema,
 } from '@documenso/lib/types/document-auth';
+import { ZRecipientEmailSchema } from '@documenso/lib/types/recipient';
 import { nanoid } from '@documenso/lib/universal/id';
 import { canRecipientBeModified as utilCanRecipientBeModified } from '@documenso/lib/utils/recipients';
 import { trpc } from '@documenso/trpc/react';
@@ -60,15 +62,15 @@ import { Input } from '@documenso/ui/primitives/input';
 import { Tooltip, TooltipContent, TooltipTrigger } from '@documenso/ui/primitives/tooltip';
 import { useToast } from '@documenso/ui/primitives/use-toast';
 
+import { AiRecipientDetectionDialog } from '~/components/dialogs/ai-recipient-detection-dialog';
+import { useCurrentTeam } from '~/providers/team';
+
 const ZEnvelopeRecipientsForm = z.object({
   signers: z.array(
     z.object({
       formId: z.string().min(1),
       id: z.number().optional(),
-      email: z
-        .string()
-        .email({ message: msg`Invalid email`.id })
-        .min(1),
+      email: ZRecipientEmailSchema,
       name: z.string(),
       role: z.nativeEnum(RecipientRole),
       signingOrder: z.number().optional(),
@@ -85,14 +87,36 @@ export const EnvelopeEditorRecipientForm = () => {
   const { envelope, setRecipientsDebounced, updateEnvelope } = useCurrentEnvelopeEditor();
 
   const organisation = useCurrentOrganisation();
+  const team = useCurrentTeam();
 
   const { t } = useLingui();
   const { toast } = useToast();
   const { remaining } = useLimits();
   const { user } = useSession();
 
+  const [searchParams, setSearchParams] = useSearchParams();
   const [recipientSearchQuery, setRecipientSearchQuery] = useState('');
 
+  // AI recipient detection dialog state
+  const [isAiDialogOpen, setIsAiDialogOpen] = useState(() => searchParams.get('ai') === 'true');
+
+  const onAiDialogOpenChange = (open: boolean) => {
+    setIsAiDialogOpen(open);
+
+    if (!open && searchParams.get('ai') === 'true') {
+      setSearchParams(
+        (prev) => {
+          const newParams = new URLSearchParams(prev);
+
+          newParams.delete('ai');
+
+          return newParams;
+        },
+        { replace: true },
+      );
+    }
+  };
+
   const debouncedRecipientSearchQuery = useDebouncedValue(recipientSearchQuery, 500);
 
   const initialId = useId();
@@ -201,12 +225,13 @@ export const EnvelopeEditorRecipientForm = () => {
     keyName: 'nativeId',
   });
 
-  const emptySigners = useCallback(
-    () => form.getValues('signers').filter((signer) => signer.email === ''),
-    [form],
+  const emptySignerIndex = watchedSigners.findIndex(
+    (signer) =>
+      !signer.name &&
+      !signer.email &&
+      envelope.fields.filter((field) => field.recipientId === signer.id).length === 0,
   );
 
-  const emptySignerIndex = watchedSigners.findIndex((signer) => !signer.name && !signer.email);
   const isUserAlreadyARecipient = watchedSigners.some(
     (signer) => signer.email.toLowerCase() === user?.email?.toLowerCase(),
   );
@@ -244,6 +269,71 @@ export const EnvelopeEditorRecipientForm = () => {
     });
   };
 
+  const onAiDetectionComplete = (detectedRecipients: TDetectedRecipientSchema[]) => {
+    const currentSigners = form.getValues('signers');
+
+    let nextSigningOrder =
+      currentSigners.length > 0
+        ? Math.max(...currentSigners.map((s) => s.signingOrder ?? 0)) + 1
+        : 1;
+
+    // If the only signer is the default empty signer lets just replace it with the detected recipients
+    if (currentSigners.length === 1 && !currentSigners[0].name && !currentSigners[0].email) {
+      form.setValue(
+        'signers',
+        detectedRecipients.map((recipient, index) => ({
+          formId: nanoid(12),
+          name: recipient.name,
+          email: recipient.email,
+          role: recipient.role,
+          actionAuth: [],
+          signingOrder: index + 1,
+        })),
+        {
+          shouldValidate: true,
+          shouldDirty: true,
+        },
+      );
+
+      return;
+    }
+
+    for (const recipient of detectedRecipients) {
+      const emailExists = currentSigners.some(
+        (s) => s.email.toLowerCase() === recipient.email.toLowerCase(),
+      );
+
+      const nameExists = currentSigners.some(
+        (s) => s.name.toLowerCase() === recipient.name.toLowerCase(),
+      );
+
+      if ((emailExists && recipient.email) || (nameExists && recipient.name)) {
+        continue;
+      }
+
+      currentSigners.push({
+        formId: nanoid(12),
+        name: recipient.name,
+        email: recipient.email,
+        role: recipient.role,
+        actionAuth: [],
+        signingOrder: nextSigningOrder,
+      });
+
+      nextSigningOrder += 1;
+    }
+
+    form.setValue('signers', normalizeSigningOrders(currentSigners), {
+      shouldValidate: true,
+      shouldDirty: true,
+    });
+
+    toast({
+      title: t`Recipients added`,
+      description: t`${detectedRecipients.length} recipient(s) have been added from AI detection.`,
+    });
+  };
+
   const onRemoveSigner = (index: number) => {
     const signer = signers[index];
 
@@ -306,8 +396,14 @@ export const EnvelopeEditorRecipientForm = () => {
     index: number,
     suggestion: RecipientAutoCompleteOption,
   ) => {
-    setValue(`signers.${index}.email`, suggestion.email);
-    setValue(`signers.${index}.name`, suggestion.name || '');
+    setValue(`signers.${index}.email`, suggestion.email, {
+      shouldValidate: true,
+      shouldDirty: true,
+    });
+    setValue(`signers.${index}.name`, suggestion.name || '', {
+      shouldValidate: true,
+      shouldDirty: true,
+    });
   };
 
   const onDragEnd = useCallback(
@@ -460,21 +556,7 @@ export const EnvelopeEditorRecipientForm = () => {
       return;
     }
 
-    const formValueSigners = formValues.signers || [];
-
-    // Remove the last signer if it's empty.
-    const nonEmptyRecipients = formValueSigners.filter((signer, i) => {
-      if (i === formValueSigners.length - 1 && signer.email === '') {
-        return false;
-      }
-
-      return true;
-    });
-
-    const validatedFormValues = ZEnvelopeRecipientsForm.safeParse({
-      ...formValues,
-      signers: nonEmptyRecipients,
-    });
+    const validatedFormValues = ZEnvelopeRecipientsForm.safeParse(formValues);
 
     if (!validatedFormValues.success) {
       return;
@@ -543,6 +625,26 @@ export const EnvelopeEditorRecipientForm = () => {
         </div>
 
         <div className="flex flex-row items-center space-x-2">
+          {team.preferences.aiFeaturesEnabled && (
+            <Tooltip>
+              <TooltipTrigger asChild>
+                <Button
+                  variant="outline"
+                  type="button"
+                  size="sm"
+                  disabled={isSubmitting}
+                  onClick={() => setIsAiDialogOpen(true)}
+                >
+                  <SparklesIcon className="h-4 w-4" />
+                </Button>
+              </TooltipTrigger>
+
+              <TooltipContent>
+                <Trans>Detect recipients with AI</Trans>
+              </TooltipContent>
+            </Tooltip>
+          )}
+
           <Button
             variant="outline"
             className="flex flex-row items-center"
@@ -570,7 +672,7 @@ export const EnvelopeEditorRecipientForm = () => {
       <CardContent>
         <AnimateGenericFadeInOut motionKey={showAdvancedSettings ? 'Show' : 'Hide'}>
           <Form {...form}>
-            <div className="bg-accent/50 -mt-2 mb-2 space-y-4 rounded-md p-4">
+            <div className="-mt-2 mb-2 space-y-4 rounded-md bg-accent/50 p-4">
               {organisation.organisationClaim.flags.cfr21 && (
                 <div className="flex flex-row items-center">
                   <Checkbox
@@ -618,9 +720,7 @@ export const EnvelopeEditorRecipientForm = () => {
                             });
                           }
                         }}
-                        disabled={
-                          isSubmitting || hasDocumentBeenSent || emptySigners().length !== 0
-                        }
+                        disabled={isSubmitting || hasDocumentBeenSent}
                       />
                     </FormControl>
 
@@ -634,7 +734,7 @@ export const EnvelopeEditorRecipientForm = () => {
 
                       <Tooltip>
                         <TooltipTrigger asChild>
-                          <span className="text-muted-foreground ml-1 cursor-help">
+                          <span className="ml-1 cursor-help text-muted-foreground">
                             <HelpCircleIcon className="h-3.5 w-3.5" />
                           </span>
                         </TooltipTrigger>
@@ -679,7 +779,7 @@ export const EnvelopeEditorRecipientForm = () => {
 
                         <Tooltip>
                           <TooltipTrigger asChild>
-                            <span className="text-muted-foreground ml-1 cursor-help">
+                            <span className="ml-1 cursor-help text-muted-foreground">
                               <HelpCircleIcon className="h-3.5 w-3.5" />
                             </span>
                           </TooltipTrigger>
@@ -716,7 +816,7 @@ export const EnvelopeEditorRecipientForm = () => {
                   >
                     {signers.map((signer, index) => (
                       <Draggable
-                        key={`${signer.id}-${signer.signingOrder}`}
+                        key={`${signer.nativeId}-${signer.signingOrder}`}
                         draggableId={signer['nativeId']}
                         index={index}
                         isDragDisabled={
@@ -732,7 +832,7 @@ export const EnvelopeEditorRecipientForm = () => {
                             {...provided.draggableProps}
                             {...provided.dragHandleProps}
                             className={cn('py-1', {
-                              'bg-widget-foreground pointer-events-none rounded-md pt-2':
+                              'pointer-events-none rounded-md bg-widget-foreground pt-2':
                                 snapshot.isDragging,
                             })}
                           >
@@ -806,7 +906,7 @@ export const EnvelopeEditorRecipientForm = () => {
                                       })}
                                     >
                                       {!showAdvancedSettings && index === 0 && (
-                                        <FormLabel required>
+                                        <FormLabel>
                                           <Trans>Email</Trans>
                                         </FormLabel>
                                       )}
@@ -860,7 +960,7 @@ export const EnvelopeEditorRecipientForm = () => {
                                       <FormControl>
                                         <RecipientAutoCompleteInput
                                           type="text"
-                                          placeholder={t`Name`}
+                                          placeholder={t`Recipient ${index + 1}`}
                                           {...field}
                                           disabled={
                                             snapshot.isDragging ||
@@ -992,6 +1092,14 @@ export const EnvelopeEditorRecipientForm = () => {
           onOpenChange={setShowSigningOrderConfirmation}
           onConfirm={handleSigningOrderDisable}
         />
+
+        <AiRecipientDetectionDialog
+          open={isAiDialogOpen}
+          onOpenChange={onAiDialogOpenChange}
+          onComplete={onAiDetectionComplete}
+          envelopeId={envelope.id}
+          teamId={envelope.teamId}
+        />
       </CardContent>
     </Card>
   );

apps/remix/app/components/general/envelope-editor/envelope-editor-upload-page.tsx

@@ -2,7 +2,7 @@ import { useMemo, useState } from 'react';
 
 import { DragDropContext, Draggable, Droppable } from '@hello-pangea/dnd';
 import type { DropResult } from '@hello-pangea/dnd';
-import { msg } from '@lingui/core/macro';
+import { msg, plural } from '@lingui/core/macro';
 import { Trans, useLingui } from '@lingui/react/macro';
 import { DocumentStatus } from '@prisma/client';
 import { FileWarningIcon, GripVerticalIcon, Loader2 } from 'lucide-react';
@@ -226,7 +226,12 @@ export const EnvelopeEditorUploadPage = () => {
     }
 
     if (maximumEnvelopeItemCount <= localFiles.length) {
-      return msg`You cannot upload more than ${maximumEnvelopeItemCount} items per envelope.`;
+      return msg({
+        message: plural(maximumEnvelopeItemCount, {
+          one: `You cannot upload more than # item per envelope.`,
+          other: `You cannot upload more than # items per envelope.`,
+        }),
+      });
     }
 
     return null;
@@ -240,7 +245,10 @@ export const EnvelopeEditorUploadPage = () => {
 
     if (maxItemsReached) {
       toast({
-        title: t`You cannot upload more than ${maximumEnvelopeItemCount} items per envelope.`,
+        title: plural(maximumEnvelopeItemCount, {
+          one: `You cannot upload more than # item per envelope.`,
+          other: `You cannot upload more than # items per envelope.`,
+        }),
         duration: 5000,
         variant: 'destructive',
       });

apps/remix/app/components/general/envelope-editor/envelope-editor.tsx

@@ -152,30 +152,30 @@ export default function EnvelopeEditor() {
     envelopeEditorSteps.find((step) => step.id === currentStep) || envelopeEditorSteps[0];
 
   return (
-    <div className="dark:bg-background h-screen w-screen bg-gray-50">
+    <div className="h-screen w-screen bg-gray-50 dark:bg-background">
       <EnvelopeEditorHeader />
 
       {/* Main Content Area */}
       <div className="flex h-[calc(100vh-4rem)] w-screen">
         {/* Left Section - Step Navigation */}
-        <div className="bg-background border-border flex w-80 flex-shrink-0 flex-col overflow-y-auto border-r py-4">
+        <div className="flex w-80 flex-shrink-0 flex-col overflow-y-auto border-r border-border bg-background py-4">
           {/* Left section step selector. */}
           <div className="px-4">
-            <h3 className="text-foreground flex items-end justify-between text-sm font-semibold">
+            <h3 className="flex items-end justify-between text-sm font-semibold text-foreground">
               {isDocument ? <Trans>Document Editor</Trans> : <Trans>Template Editor</Trans>}
 
-              <span className="text-muted-foreground bg-muted/50 ml-2 rounded border px-2 py-0.5 text-xs">
+              <span className="ml-2 rounded border bg-muted/50 px-2 py-0.5 text-xs text-muted-foreground">
                 <Trans context="The step counter">
                   Step {currentStepData.order}/{envelopeEditorSteps.length}
                 </Trans>
               </span>
             </h3>
 
-            <div className="bg-muted relative my-4 h-[4px] rounded-md">
+            <div className="relative my-4 h-[4px] rounded-md bg-muted">
               <motion.div
                 layout="size"
                 layoutId="document-flow-container-step"
-                className="bg-documenso absolute inset-y-0 left-0"
+                className="absolute inset-y-0 left-0 bg-documenso"
                 style={{
                   width: `${(100 / envelopeEditorSteps.length) * (currentStepData.order ?? 0)}%`,
                 }}
@@ -219,7 +219,7 @@ export default function EnvelopeEditor() {
                         >
                           {t(step.title)}
                         </div>
-                        <div className="text-muted-foreground text-xs">{t(step.description)}</div>
+                        <div className="text-xs text-muted-foreground">{t(step.description)}</div>
                       </div>
                     </div>
                   </div>
@@ -232,7 +232,7 @@ export default function EnvelopeEditor() {
 
           {/* Quick Actions. */}
           <div className="space-y-3 px-4">
-            <h4 className="text-foreground text-sm font-semibold">
+            <h4 className="text-sm font-semibold text-foreground">
               <Trans>Quick Actions</Trans>
             </h4>
             <EnvelopeEditorSettingsDialog
@@ -246,10 +246,6 @@ export default function EnvelopeEditor() {
 
             {isDocument && (
               <EnvelopeDistributeDialog
-                envelope={{
-                  ...envelope,
-                  fields: editorFields.localFields,
-                }}
                 documentRootPath={relativePath.documentRootPath}
                 trigger={
                   <Button variant="ghost" size="sm" className="w-full justify-start">

apps/remix/app/components/general/envelope-editor/envelope-recipient-selector.tsx

@@ -1,5 +1,7 @@
 import { useCallback, useState } from 'react';
 
+import type { I18n } from '@lingui/core';
+import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react/macro';
 import { Trans } from '@lingui/react/macro';
 import type { Field, Recipient } from '@prisma/client';
@@ -39,8 +41,15 @@ export const EnvelopeRecipientSelector = ({
   fields,
   align = 'start',
 }: EnvelopeRecipientSelectorProps) => {
+  const { i18n } = useLingui();
+
   const [showRecipientsSelector, setShowRecipientsSelector] = useState(false);
 
+  const getRecipientLabel = useCallback(
+    (recipient: Recipient) => extractRecipientLabel(recipient, recipients, i18n),
+    [recipients],
+  );
+
   return (
     <Popover open={showRecipientsSelector} onOpenChange={setShowRecipientsSelector}>
       <PopoverTrigger asChild>
@@ -49,7 +58,7 @@ export const EnvelopeRecipientSelector = ({
           variant="outline"
           role="combobox"
           className={cn(
-            'bg-background text-muted-foreground hover:text-foreground justify-between font-normal',
+            'justify-between bg-background font-normal text-muted-foreground hover:text-foreground',
             getRecipientColorStyles(
               Math.max(
                 recipients.findIndex((r) => r.id === selectedRecipient?.id),
@@ -59,16 +68,12 @@ export const EnvelopeRecipientSelector = ({
             className,
           )}
         >
-          {selectedRecipient?.email && (
+          {selectedRecipient && (
             <span className="flex-1 truncate text-left">
-              {selectedRecipient?.name} ({selectedRecipient?.email})
+              {getRecipientLabel(selectedRecipient)}
             </span>
           )}
 
-          {!selectedRecipient?.email && (
-            <span className="flex-1 truncate text-left">{selectedRecipient?.email}</span>
-          )}
-
           <ChevronsUpDown className="ml-2 h-4 w-4" />
         </Button>
       </PopoverTrigger>
@@ -105,7 +110,7 @@ export const EnvelopeRecipientSelectorCommand = ({
   fields,
   placeholder,
 }: EnvelopeRecipientSelectorCommandProps) => {
-  const { t } = useLingui();
+  const { t, i18n } = useLingui();
 
   const recipientsByRole = useCallback(() => {
     const recipientsByRole: Record<RecipientRole, Recipient[]> = {
@@ -154,6 +159,11 @@ export const EnvelopeRecipientSelectorCommand = ({
     [fields, recipients],
   );
 
+  const getRecipientLabel = useCallback(
+    (recipient: Recipient) => extractRecipientLabel(recipient, recipients, i18n),
+    [recipients],
+  );
+
   return (
     <Command
       value={selectedRecipient ? selectedRecipient.id.toString() : undefined}
@@ -162,21 +172,21 @@ export const EnvelopeRecipientSelectorCommand = ({
       <CommandInput placeholder={placeholder} />
 
       <CommandEmpty>
-        <span className="text-muted-foreground inline-block px-4">
+        <span className="inline-block px-4 text-muted-foreground">
           <Trans>No recipient matching this description was found.</Trans>
         </span>
       </CommandEmpty>
 
       {recipientsByRoleToDisplay().map(([role, roleRecipients], roleIndex) => (
         <CommandGroup key={roleIndex}>
-          <div className="text-muted-foreground mb-1 ml-2 mt-2 text-xs font-medium">
+          <div className="mb-1 ml-2 mt-2 text-xs font-medium text-muted-foreground">
             {t(RECIPIENT_ROLES_DESCRIPTION[role].roleNamePlural)}
           </div>
 
           {roleRecipients.length === 0 && (
             <div
               key={`${role}-empty`}
-              className="text-muted-foreground/80 px-4 pb-4 pt-2.5 text-center text-xs"
+              className="px-4 pb-4 pt-2.5 text-center text-xs text-muted-foreground/80"
             >
               <Trans>No recipients with this role</Trans>
             </div>
@@ -205,18 +215,12 @@ export const EnvelopeRecipientSelectorCommand = ({
               }}
             >
               <span
-                className={cn('text-foreground/70 truncate', {
+                className={cn('truncate text-foreground/70', {
                   'text-foreground/80': recipient.id === selectedRecipient?.id,
                   'opacity-50': isRecipientDisabled(recipient.id),
                 })}
               >
-                {recipient.name && (
-                  <span title={`${recipient.name} (${recipient.email})`}>
-                    {recipient.name} ({recipient.email})
-                  </span>
-                )}
-
-                {!recipient.name && <span title={recipient.email}>{recipient.email}</span>}
+                {getRecipientLabel(recipient)}
               </span>
 
               <div className="ml-auto flex items-center justify-center">
@@ -234,7 +238,7 @@ export const EnvelopeRecipientSelectorCommand = ({
                       <Info className="z-50 ml-2 h-4 w-4" />
                     </TooltipTrigger>
 
-                    <TooltipContent className="text-muted-foreground max-w-xs">
+                    <TooltipContent className="max-w-xs text-muted-foreground">
                       <Trans>
                         This document has already been sent to this recipient. You can no longer
                         edit this recipient.
@@ -250,3 +254,22 @@ export const EnvelopeRecipientSelectorCommand = ({
     </Command>
   );
 };
+
+const extractRecipientLabel = (recipient: Recipient, recipients: Recipient[], i18n: I18n) => {
+  if (recipient.name && recipient.email) {
+    return `${recipient.name} (${recipient.email})`;
+  }
+
+  if (recipient.name) {
+    return recipient.name;
+  }
+
+  if (recipient.email) {
+    return recipient.email;
+  }
+
+  // Since objects are basically pointers we can use `indexOf` rather than `findIndex`
+  const index = recipients.indexOf(recipient);
+
+  return i18n._(msg`Recipient ${index + 1}`);
+};

apps/remix/app/components/general/envelope-signing/envelope-signing-complete-dialog.tsx

@@ -80,12 +80,14 @@ export const EnvelopeSignerCompleteDialog = () => {
   const handleOnCompleteClick = async (
     nextSigner?: { name: string; email: string },
     accessAuthOptions?: TRecipientAccessAuth,
+    recipientDetails?: { name: string; email: string },
   ) => {
     try {
       await completeDocument({
         token: recipient.token,
         documentId: mapSecondaryIdToDocumentId(envelope.secondaryId),
         accessAuthOptions,
+        recipientOverride: recipientDetails,
         ...(nextSigner?.email && nextSigner?.name ? { nextSigner } : {}),
       });
 
@@ -205,21 +207,30 @@ export const EnvelopeSignerCompleteDialog = () => {
     }
   };
 
-  const directTemplatePayload = useMemo(() => {
+  const recipientPayload = useMemo(() => {
     if (!isDirectTemplate) {
-      return;
+      return {
+        name:
+          recipient.name ||
+          recipient.fields.find((field) => field.type === FieldType.NAME)?.customText ||
+          '',
+        email:
+          recipient.email ||
+          recipient.fields.find((field) => field.type === FieldType.EMAIL)?.customText ||
+          '',
+      };
     }
 
     return {
       name: fullName,
       email: email,
     };
-  }, [email, fullName, isDirectTemplate]);
+  }, [email, fullName, isDirectTemplate, recipient.email, recipient.name, recipient.fields]);
 
   return (
     <DocumentSigningCompleteDialog
       isSubmitting={isPending}
-      directTemplatePayload={directTemplatePayload}
+      recipientPayload={recipientPayload}
       onSignatureComplete={
         isDirectTemplate ? handleDirectTemplateCompleteClick : handleOnCompleteClick
       }
@@ -230,6 +241,7 @@ export const EnvelopeSignerCompleteDialog = () => {
       allowDictateNextSigner={Boolean(
         nextRecipient && envelope.documentMeta.allowDictateNextSigner,
       )}
+      disableNameInput={!isDirectTemplate && recipient.name !== ''}
       defaultNextSigner={
         nextRecipient ? { name: nextRecipient.name, email: nextRecipient.email } : undefined
       }

apps/remix/app/components/general/envelope/envelope-drop-zone-wrapper.tsx

@@ -1,5 +1,6 @@
 import { type ReactNode, useState } from 'react';
 
+import { plural } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react/macro';
 import { Trans } from '@lingui/react/macro';
 import { EnvelopeType } from '@prisma/client';
@@ -115,7 +116,9 @@ export const EnvelopeDropZoneWrapper = ({
           ? formatDocumentsPath(team.url)
           : formatTemplatesPath(team.url);
 
-      await navigate(`${pathPrefix}/${id}/edit`);
+      const aiQueryParam = team.preferences.aiFeaturesEnabled ? '?ai=true' : '';
+
+      await navigate(`${pathPrefix}/${id}/edit${aiQueryParam}`);
     } catch (err) {
       const error = AppError.parseError(err);
 
@@ -153,7 +156,10 @@ export const EnvelopeDropZoneWrapper = ({
 
     if (maxItemsReached) {
       toast({
-        title: t`You cannot upload more than ${maximumEnvelopeItemCount} items per envelope.`,
+        title: plural(maximumEnvelopeItemCount, {
+          one: `You cannot upload more than # item per envelope.`,
+          other: `You cannot upload more than # items per envelope.`,
+        }),
         duration: 5000,
         variant: 'destructive',
       });
@@ -220,9 +226,9 @@ export const EnvelopeDropZoneWrapper = ({
       {children}
 
       {isDragActive && (
-        <div className="bg-muted/60 fixed left-0 top-0 z-[9999] h-full w-full backdrop-blur-[4px]">
+        <div className="fixed left-0 top-0 z-[9999] h-full w-full bg-muted/60 backdrop-blur-[4px]">
           <div className="pointer-events-none flex h-full w-full flex-col items-center justify-center">
-            <h2 className="text-foreground text-2xl font-semibold">
+            <h2 className="text-2xl font-semibold text-foreground">
               {type === EnvelopeType.DOCUMENT ? (
                 <Trans>Upload Document</Trans>
               ) : (
@@ -230,7 +236,7 @@ export const EnvelopeDropZoneWrapper = ({
               )}
             </h2>
 
-            <p className="text-muted-foreground text-md mt-4">
+            <p className="text-md mt-4 text-muted-foreground">
               <Trans>Drag and drop your PDF file here</Trans>
             </p>
 
@@ -247,7 +253,7 @@ export const EnvelopeDropZoneWrapper = ({
               team?.id === undefined &&
               remaining.documents > 0 &&
               Number.isFinite(remaining.documents) && (
-                <p className="text-muted-foreground/80 mt-4 text-sm">
+                <p className="mt-4 text-sm text-muted-foreground/80">
                   <Trans>
                     {remaining.documents} of {quota.documents} documents remaining this month.
                   </Trans>
@@ -258,10 +264,10 @@ export const EnvelopeDropZoneWrapper = ({
       )}
 
       {isLoading && (
-        <div className="bg-muted/30 absolute inset-0 z-50 backdrop-blur-[2px]">
+        <div className="absolute inset-0 z-50 bg-muted/30 backdrop-blur-[2px]">
           <div className="pointer-events-none flex h-1/2 w-full flex-col items-center justify-center">
-            <Loader className="text-primary h-12 w-12 animate-spin" />
-            <p className="text-foreground mt-8 font-medium">
+            <Loader className="h-12 w-12 animate-spin text-primary" />
+            <p className="mt-8 font-medium text-foreground">
               <Trans>Uploading</Trans>
             </p>
           </div>

apps/remix/app/components/general/envelope/envelope-upload-button.tsx

@@ -1,6 +1,6 @@
 import { useMemo, useState } from 'react';
 
-import { msg } from '@lingui/core/macro';
+import { msg, plural } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react/macro';
 import { Trans } from '@lingui/react/macro';
 import { EnvelopeType } from '@prisma/client';
@@ -108,7 +108,9 @@ export const EnvelopeUploadButton = ({ className, type, folderId }: EnvelopeUplo
           ? formatDocumentsPath(team.url)
           : formatTemplatesPath(team.url);
 
-      await navigate(`${pathPrefix}/${id}/edit`);
+      const aiQueryParam = team.preferences.aiFeaturesEnabled ? '?ai=true' : '';
+
+      await navigate(`${pathPrefix}/${id}/edit${aiQueryParam}`);
 
       toast({
         title: type === EnvelopeType.DOCUMENT ? t`Document uploaded` : t`Template uploaded`,
@@ -153,7 +155,10 @@ export const EnvelopeUploadButton = ({ className, type, folderId }: EnvelopeUplo
 
     if (maxItemsReached) {
       toast({
-        title: t`You cannot upload more than ${maximumEnvelopeItemCount} items per envelope.`,
+        title: plural(maximumEnvelopeItemCount, {
+          one: `You cannot upload more than # item per envelope.`,
+          other: `You cannot upload more than # items per envelope.`,
+        }),
         duration: 5000,
         variant: 'destructive',
       });

apps/remix/app/components/general/stack-avatars-with-tooltip.tsx

@@ -83,8 +83,8 @@ export const StackAvatarsWithTooltip = ({
                 fallbackText={recipientAbbreviation(recipient)}
               />
               <div>
-                <p className="text-muted-foreground text-sm">{recipient.email}</p>
-                <p className="text-muted-foreground/70 text-xs">
+                <p className="text-sm text-muted-foreground">{recipient.email || recipient.name}</p>
+                <p className="text-xs text-muted-foreground/70">
                   {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
                 </p>
               </div>
@@ -107,8 +107,8 @@ export const StackAvatarsWithTooltip = ({
                 fallbackText={recipientAbbreviation(recipient)}
               />
               <div>
-                <p className="text-muted-foreground text-sm">{recipient.email}</p>
-                <p className="text-muted-foreground/70 text-xs">
+                <p className="text-sm text-muted-foreground">{recipient.email || recipient.name}</p>
+                <p className="text-xs text-muted-foreground/70">
                   {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
                 </p>
               </div>

apps/remix/app/components/tables/admin-dashboard-users-table.tsx

@@ -51,7 +51,7 @@ export const AdminDashboardUsersTable = ({
   const columns = useMemo(() => {
     return [
       {
-        header: 'ID',
+        header: _(msg`ID`),
         accessorKey: 'id',
         cell: ({ row }) => <div>{row.original.id}</div>,
       },

apps/remix/app/components/tables/admin-document-recipient-item-table.tsx

@@ -57,7 +57,7 @@ export const AdminDocumentRecipientItemTable = ({ recipient }: RecipientItemProp
   const columns = useMemo(() => {
     return [
       {
-        header: 'ID',
+        header: _(msg`ID`),
         accessorKey: 'id',
         cell: ({ row }) => <div>{row.original.id}</div>,
       },

apps/remix/app/components/tables/admin-organisations-table.tsx

@@ -113,7 +113,11 @@ export const AdminOrganisationsTable = ({
                 isPaid ? 'bg-green-100 text-green-800' : 'bg-gray-100 text-gray-800'
               }`}
             >
-              {isPaid ? t`Paid` : t`Free`}
+              {isPaid ? (
+                <Trans context="Subscription status">Paid</Trans>
+              ) : (
+                <Trans context="Subscription status">Free</Trans>
+              )}
             </div>
           );
         },
@@ -131,7 +135,7 @@ export const AdminOrganisationsTable = ({
               <ExternalLinkIcon className="h-4 w-4" />
             </Link>
           ) : (
-            'None'
+            <Trans>None</Trans>
           ),
       },
       {

apps/remix/app/components/tables/document-logs-table.tsx

@@ -96,11 +96,11 @@ export const DocumentLogsTable = ({ documentId }: DocumentLogsTableProps) => {
         cell: ({ row }) => <span>{formatDocumentAuditLogAction(_, row.original).description}</span>,
       },
       {
-        header: 'IP Address',
+        header: _(msg`IP Address`),
         accessorKey: 'ipAddress',
       },
       {
-        header: 'Browser',
+        header: _(msg`Browser`),
         cell: ({ row }) => {
           if (!row.original.userAgent) {
             return 'N/A';

apps/remix/app/components/tables/settings-security-activity-table.tsx

@@ -104,7 +104,7 @@ export const SettingsSecurityActivityTable = () => {
         },
       },
       {
-        header: 'IP Address',
+        header: _(msg`IP Address`),
         accessorKey: 'ipAddress',
         cell: ({ row }) => row.original.ipAddress ?? 'N/A',
       },

apps/remix/app/components/tables/user-billing-organisations-table.tsx

@@ -28,19 +28,19 @@ export const UserBillingOrganisationsTable = () => {
   const getSubscriptionStatusDisplay = (status: SubscriptionStatus | undefined) => {
     return match(status)
       .with(SubscriptionStatus.ACTIVE, () => ({
-        label: t`Active`,
+        label: t({ message: `Active`, context: `Subscription status` }),
         variant: 'default' as const,
       }))
       .with(SubscriptionStatus.PAST_DUE, () => ({
-        label: t`Past Due`,
+        label: t({ message: `Past Due`, context: `Subscription status` }),
         variant: 'warning' as const,
       }))
       .with(SubscriptionStatus.INACTIVE, () => ({
-        label: t`Inactive`,
+        label: t({ message: `Inactive`, context: `Subscription status` }),
         variant: 'neutral' as const,
       }))
       .otherwise(() => ({
-        label: t`Free`,
+        label: t({ message: `Free`, context: `Subscription status` }),
         variant: 'neutral' as const,
       }));
   };

apps/remix/app/entry.client.tsx

@@ -10,6 +10,8 @@ import { HydratedRouter } from 'react-router/dom';
 import { extractPostHogConfig } from '@documenso/lib/constants/feature-flags';
 import { dynamicActivate } from '@documenso/lib/utils/i18n';
 
+import './utils/polyfills/promise-with-resolvers';
+
 function PosthogInit() {
   const postHogConfig = extractPostHogConfig();
 

apps/remix/app/root.tsx

@@ -46,12 +46,16 @@ export async function loader({ request }: Route.LoaderArgs) {
 
   const { getTheme } = await themeSessionResolver(request);
 
-  let lang: SupportedLanguageCodes = await langCookie.parse(request.headers.get('cookie') ?? '');
+  const cookieHeader = request.headers.get('cookie') ?? '';
+
+  let lang: SupportedLanguageCodes = await langCookie.parse(cookieHeader);
 
   if (!APP_I18N_OPTIONS.supportedLangs.includes(lang)) {
     lang = extractLocaleData({ headers: request.headers }).lang;
   }
 
+  const disableAnimations = cookieHeader.includes('__disable_animations=true');
+
   let organisations = null;
 
   if (session.isAuthenticated) {
@@ -62,6 +66,7 @@ export async function loader({ request }: Route.LoaderArgs) {
     {
       lang,
       theme: getTheme(),
+      disableAnimations,
       session: session.isAuthenticated
         ? {
             user: session.user,
@@ -92,7 +97,8 @@ export function Layout({ children }: { children: React.ReactNode }) {
 }
 
 export function LayoutContent({ children }: { children: React.ReactNode }) {
-  const { publicEnv, session, lang, ...data } = useLoaderData<typeof loader>() || {};
+  const { publicEnv, session, lang, disableAnimations, ...data } =
+    useLoaderData<typeof loader>() || {};
 
   const [theme] = useTheme();
 
@@ -111,6 +117,14 @@ export function LayoutContent({ children }: { children: React.ReactNode }) {
         <meta name="google" content="notranslate" />
         <PreventFlashOnWrongTheme ssrTheme={Boolean(data.theme)} />
 
+        {disableAnimations && (
+          <style
+            dangerouslySetInnerHTML={{
+              __html: `*, *::before, *::after { animation: none !important; transition: none !important; }`,
+            }}
+          />
+        )}
+
         {/* Fix: https://stackoverflow.com/questions/21147149/flash-of-unstyled-content-fouc-in-firefox-only-is-ff-slow-renderer */}
         <script>0</script>
       </head>

apps/remix/app/routes/_authenticated+/admin+/documents._index.tsx

@@ -114,7 +114,7 @@ export default function AdminDocumentsPage() {
         },
       },
       {
-        header: 'Last updated',
+        header: _(msg`Last updated`),
         accessorKey: 'updatedAt',
         cell: ({ row }) => i18n.date(row.original.updatedAt),
       },

apps/remix/app/routes/_authenticated+/admin+/stats.tsx

@@ -152,12 +152,6 @@ export default function AdminStatsPage({ loaderData }: Route.ComponentProps) {
         <div className="mt-5 grid grid-cols-2 gap-8">
           <MonthlyActiveUsersChart title={_(msg`MAU (signed in)`)} data={monthlyActiveUsers} />
 
-          <MonthlyActiveUsersChart
-            title={_(msg`Cumulative MAU (signed in)`)}
-            data={monthlyActiveUsers}
-            cummulative
-          />
-
           <AdminStatsUsersWithDocumentsChart
             data={monthlyUsersWithDocuments}
             title={_(msg`MAU (created document)`)}

apps/remix/app/routes/_authenticated+/o.$orgUrl.settings.document.tsx

@@ -1,8 +1,10 @@
 import { useLingui } from '@lingui/react/macro';
 import { Loader } from 'lucide-react';
+import { useLoaderData } from 'react-router';
 
 import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/organisation';
 import { useSession } from '@documenso/lib/client-only/providers/session';
+import { IS_AI_FEATURES_CONFIGURED } from '@documenso/lib/constants/app';
 import { DocumentSignatureType } from '@documenso/lib/constants/document';
 import { isPersonalLayout } from '@documenso/lib/utils/organisations';
 import { trpc } from '@documenso/trpc/react';
@@ -19,9 +21,16 @@ export function meta() {
   return appMetaTags('Document Preferences');
 }
 
-export default function OrganisationSettingsDocumentPage() {
-  const { organisations } = useSession();
+export const loader = () => {
+  return {
+    isAiFeaturesConfigured: IS_AI_FEATURES_CONFIGURED(),
+  };
+};
 
+export default function OrganisationSettingsDocumentPage() {
+  const { isAiFeaturesConfigured } = useLoaderData<typeof loader>();
+
+  const { organisations } = useSession();
   const organisation = useCurrentOrganisation();
 
   const { t } = useLingui();
@@ -48,6 +57,7 @@ export default function OrganisationSettingsDocumentPage() {
         includeSigningCertificate,
         includeAuditLog,
         signatureTypes,
+        aiFeaturesEnabled,
       } = data;
 
       if (
@@ -56,7 +66,8 @@ export default function OrganisationSettingsDocumentPage() {
         documentDateFormat === null ||
         includeSenderDetails === null ||
         includeSigningCertificate === null ||
-        includeAuditLog === null
+        includeAuditLog === null ||
+        aiFeaturesEnabled === null
       ) {
         throw new Error('Should not be possible.');
       }
@@ -74,6 +85,7 @@ export default function OrganisationSettingsDocumentPage() {
           typedSignatureEnabled: signatureTypes.includes(DocumentSignatureType.TYPE),
           uploadSignatureEnabled: signatureTypes.includes(DocumentSignatureType.UPLOAD),
           drawSignatureEnabled: signatureTypes.includes(DocumentSignatureType.DRAW),
+          aiFeaturesEnabled,
         },
       });
 
@@ -93,7 +105,7 @@ export default function OrganisationSettingsDocumentPage() {
   if (isLoadingOrganisation || !organisationWithSettings) {
     return (
       <div className="flex items-center justify-center rounded-lg py-32">
-        <Loader className="text-muted-foreground h-6 w-6 animate-spin" />
+        <Loader className="h-6 w-6 animate-spin text-muted-foreground" />
       </div>
     );
   }
@@ -110,6 +122,7 @@ export default function OrganisationSettingsDocumentPage() {
       <section>
         <DocumentPreferencesForm
           canInherit={false}
+          isAiFeaturesConfigured={isAiFeaturesConfigured}
           settings={organisationWithSettings.organisationGlobalSettings}
           onFormSubmit={onDocumentPreferencesFormSubmit}
         />

apps/remix/app/routes/_authenticated+/settings+/_dynamic_personal_routes+/document.tsx

@@ -1,5 +1,5 @@
-import DocumentPage, { meta } from '../../o.$orgUrl.settings.document';
+import DocumentPage, { loader, meta } from '../../o.$orgUrl.settings.document';
 
-export { meta };
+export { meta, loader };
 
 export default DocumentPage;

apps/remix/app/routes/_authenticated+/t.$teamUrl+/settings.document.tsx

@@ -1,6 +1,8 @@
 import { useLingui } from '@lingui/react/macro';
 import { Loader } from 'lucide-react';
+import { useLoaderData } from 'react-router';
 
+import { IS_AI_FEATURES_CONFIGURED } from '@documenso/lib/constants/app';
 import { DocumentSignatureType } from '@documenso/lib/constants/document';
 import { trpc } from '@documenso/trpc/react';
 import { useToast } from '@documenso/ui/primitives/use-toast';
@@ -17,7 +19,15 @@ export function meta() {
   return appMetaTags('Document Preferences');
 }
 
+export const loader = () => {
+  return {
+    isAiFeaturesConfigured: IS_AI_FEATURES_CONFIGURED(),
+  };
+};
+
 export default function TeamsSettingsPage() {
+  const { isAiFeaturesConfigured } = useLoaderData<typeof loader>();
+
   const team = useCurrentTeam();
 
   const { t } = useLingui();
@@ -40,6 +50,7 @@ export default function TeamsSettingsPage() {
         includeSigningCertificate,
         includeAuditLog,
         signatureTypes,
+        aiFeaturesEnabled,
       } = data;
 
       await updateTeamSettings({
@@ -52,6 +63,7 @@ export default function TeamsSettingsPage() {
           includeSenderDetails,
           includeSigningCertificate,
           includeAuditLog,
+          aiFeaturesEnabled,
           ...(signatureTypes.length === 0
             ? {
                 typedSignatureEnabled: null,
@@ -82,7 +94,7 @@ export default function TeamsSettingsPage() {
   if (isLoadingTeam || !teamWithSettings) {
     return (
       <div className="flex items-center justify-center rounded-lg py-32">
-        <Loader className="text-muted-foreground h-6 w-6 animate-spin" />
+        <Loader className="h-6 w-6 animate-spin text-muted-foreground" />
       </div>
     );
   }
@@ -97,6 +109,7 @@ export default function TeamsSettingsPage() {
       <section>
         <DocumentPreferencesForm
           canInherit={true}
+          isAiFeaturesConfigured={isAiFeaturesConfigured}
           settings={teamWithSettings.teamSettings}
           onFormSubmit={onDocumentPreferencesSubmit}
         />

apps/remix/app/routes/_unauthenticated+/organisation.sso.confirmation.$token.tsx

@@ -1,6 +1,7 @@
 import { useState } from 'react';
 
 import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
 import { AlertTriangle, Building2, Database, Eye, Settings, UserCircle2 } from 'lucide-react';
 import { data, isRouteErrorResponse } from 'react-router';
@@ -125,6 +126,7 @@ export async function loader({ params }: Route.LoaderArgs) {
 export default function OrganisationSsoConfirmationTokenPage({ loaderData }: Route.ComponentProps) {
   const { token, type, user, organisation } = loaderData;
 
+  const { _ } = useLingui();
   const { toast } = useToast();
   const navigate = useNavigate();
 
@@ -136,12 +138,12 @@ export default function OrganisationSsoConfirmationTokenPage({ loaderData }: Rou
         await navigate('/');
 
         toast({
-          title: 'Account link declined',
+          title: _(msg`Account link declined`),
         });
       },
       onError: (error) => {
         toast({
-          title: 'Error declining account link',
+          title: _(msg`Error declining account link`),
           description: error.message,
         });
       },
@@ -153,12 +155,12 @@ export default function OrganisationSsoConfirmationTokenPage({ loaderData }: Rou
         await navigate(formatOrganisationLoginPath(organisation.url));
 
         toast({
-          title: 'Account linked successfully',
+          title: _(msg`Account linked successfully`),
         });
       },
       onError: (error) => {
         toast({
-          title: 'Error linking account',
+          title: _(msg`Error linking account`),
           description: error.message,
         });
       },

apps/remix/app/routes/embed+/v1+/authoring+/document.edit.$id.tsx

@@ -41,7 +41,9 @@ export const loader = async ({ request, params }: Route.LoaderArgs) => {
   const token = url.searchParams.get('token') || '';
 
   // We also know that the token is valid, but we need the userId + teamId
-  const result = await verifyEmbeddingPresignToken({ token }).catch(() => null);
+  const result = await verifyEmbeddingPresignToken({ token, scope: `documentId:${id}` }).catch(
+    () => null,
+  );
 
   if (!result) {
     throw new Error('Invalid token');

apps/remix/app/routes/embed+/v1+/authoring+/template.edit.$id.tsx

@@ -41,7 +41,9 @@ export const loader = async ({ request, params }: Route.LoaderArgs) => {
   const token = url.searchParams.get('token') || '';
 
   // We also know that the token is valid, but we need the userId + teamId
-  const result = await verifyEmbeddingPresignToken({ token }).catch(() => null);
+  const result = await verifyEmbeddingPresignToken({ token, scope: `templateId:${id}` }).catch(
+    () => null,
+  );
 
   if (!result) {
     throw new Error('Invalid token');

apps/remix/app/utils/polyfills/promise-with-resolvers.ts

@@ -0,0 +1,30 @@
+/**
+ * Polyfill for Promise.withResolvers (ES2024)
+ * @see https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/Promise/withResolvers
+ */
+
+type PromiseWithResolvers<T> = {
+  promise: Promise<T>;
+  resolve: (value: T | PromiseLike<T>) => void;
+  reject: (reason?: unknown) => void;
+};
+
+// We're patching here
+// eslint-disable-next-line @typescript-eslint/no-explicit-any
+const GlobalPromise = globalThis.Promise as any;
+
+if (typeof GlobalPromise.withResolvers !== 'function') {
+  GlobalPromise.withResolvers = function <T>(): PromiseWithResolvers<T> {
+    let resolve!: (value: T | PromiseLike<T>) => void;
+    let reject!: (reason?: unknown) => void;
+
+    const promise = new Promise<T>((res, rej) => {
+      resolve = res;
+      reject = rej;
+    });
+
+    return { promise, resolve, reject };
+  };
+}
+
+export {};

apps/remix/package.json

@@ -108,5 +108,5 @@
     "vite-plugin-babel-macros": "^1.0.6",
     "vite-tsconfig-paths": "^5.1.4"
   },
-  "version": "2.1.0"
+  "version": "2.2.5"
 }

apps/remix/server/api/ai/detect-fields.client.ts

@@ -0,0 +1,161 @@
+import { z } from 'zod';
+
+import {
+  type TDetectFieldsRequest,
+  ZNormalizedFieldWithContextSchema,
+} from './detect-fields.types';
+
+export type { TDetectFieldsRequest };
+
+// Stream event schemas
+const ZProgressEventSchema = z.object({
+  type: z.literal('progress'),
+  pagesProcessed: z.number(),
+  totalPages: z.number(),
+  fieldsDetected: z.number(),
+});
+
+const ZKeepaliveEventSchema = z.object({
+  type: z.literal('keepalive'),
+});
+
+const ZErrorEventSchema = z.object({
+  type: z.literal('error'),
+  message: z.string(),
+});
+
+const ZCompleteEventSchema = z.object({
+  type: z.literal('complete'),
+  fields: z.array(ZNormalizedFieldWithContextSchema),
+});
+
+const ZStreamEventSchema = z.discriminatedUnion('type', [
+  ZProgressEventSchema,
+  ZKeepaliveEventSchema,
+  ZErrorEventSchema,
+  ZCompleteEventSchema,
+]);
+
+export type DetectFieldsProgressEvent = z.infer<typeof ZProgressEventSchema>;
+export type DetectFieldsCompleteEvent = z.infer<typeof ZCompleteEventSchema>;
+export type DetectFieldsStreamEvent = z.infer<typeof ZStreamEventSchema>;
+
+const ZApiErrorResponseSchema = z.object({
+  error: z.string(),
+});
+
+export class AiApiError extends Error {
+  constructor(
+    message: string,
+    public status: number,
+  ) {
+    super(message);
+    this.name = 'AiApiError';
+  }
+}
+
+export type DetectFieldsOptions = {
+  request: TDetectFieldsRequest;
+  onProgress?: (event: DetectFieldsProgressEvent) => void;
+  onComplete: (event: DetectFieldsCompleteEvent) => void;
+  onError: (error: AiApiError) => void;
+  signal?: AbortSignal;
+};
+
+/**
+ * Detect fields from an envelope using AI with streaming support.
+ */
+export const detectFields = async ({
+  request,
+  onProgress,
+  onComplete,
+  onError,
+  signal,
+}: DetectFieldsOptions): Promise<void> => {
+  const response = await fetch('/api/ai/detect-fields', {
+    method: 'POST',
+    headers: {
+      'Content-Type': 'application/json',
+    },
+    body: JSON.stringify(request),
+    signal,
+  });
+
+  // Handle non-streaming error responses (auth failures, etc.)
+  if (!response.ok) {
+    const text = await response.text();
+
+    try {
+      const parsed = ZApiErrorResponseSchema.parse(JSON.parse(text));
+
+      throw new AiApiError(parsed.error, response.status);
+    } catch (e) {
+      if (e instanceof AiApiError) {
+        throw e;
+      }
+
+      throw new AiApiError('Failed to detect fields', response.status);
+    }
+  }
+
+  // Handle streaming response
+  const reader = response.body?.getReader();
+
+  if (!reader) {
+    throw new AiApiError('No response body', 500);
+  }
+
+  const decoder = new TextDecoder();
+  let buffer = '';
+
+  try {
+    let done = false;
+
+    while (!done) {
+      const result = await reader.read();
+      done = result.done;
+
+      if (done) {
+        break;
+      }
+
+      const value = result.value;
+
+      buffer += decoder.decode(value, { stream: true });
+
+      // Process complete lines
+      const lines = buffer.split('\n');
+      buffer = lines.pop() || ''; // Keep incomplete line in buffer
+
+      for (const line of lines) {
+        if (!line.trim()) {
+          continue;
+        }
+
+        try {
+          const event = ZStreamEventSchema.parse(JSON.parse(line));
+
+          switch (event.type) {
+            case 'progress':
+              onProgress?.(event);
+              break;
+            case 'keepalive':
+              // Ignore keepalive, it's just to prevent timeout
+              break;
+            case 'error':
+              onError(new AiApiError(event.message, 500));
+              return;
+            case 'complete':
+              onComplete(event);
+              return;
+          }
+        } catch {
+          // Ignore malformed lines
+          console.warn('Failed to parse stream event:', line);
+        }
+      }
+    }
+  } finally {
+    reader.releaseLock();
+  }
+};

apps/remix/server/api/ai/detect-fields.ts

@@ -0,0 +1,154 @@
+import { sValidator } from '@hono/standard-validator';
+import { Hono } from 'hono';
+import { streamText } from 'hono/streaming';
+
+import { getSession } from '@documenso/auth/server/lib/utils/get-session';
+import { IS_AI_FEATURES_CONFIGURED } from '@documenso/lib/constants/app';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { detectFieldsFromEnvelope } from '@documenso/lib/server-only/ai/envelope/detect-fields';
+import { getTeamById } from '@documenso/lib/server-only/team/get-team';
+
+import type { HonoEnv } from '../../router';
+import { ZDetectFieldsRequestSchema } from './detect-fields.types';
+
+const KEEPALIVE_INTERVAL_MS = 5000;
+
+export const detectFieldsRoute = new Hono<HonoEnv>().post(
+  '/',
+  sValidator('json', ZDetectFieldsRequestSchema),
+  async (c) => {
+    const logger = c.get('logger');
+
+    try {
+      const { envelopeId, teamId, context } = c.req.valid('json');
+
+      const session = await getSession(c);
+
+      if (!session.user) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'You must be logged in to detect fields',
+        });
+      }
+
+      // Verify user has access to the team (abort early)
+      const team = await getTeamById({
+        userId: session.user.id,
+        teamId,
+      }).catch(() => null);
+
+      if (!team) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'You do not have access to this team',
+        });
+      }
+
+      // Check if AI features are enabled for the team
+      const { aiFeaturesEnabled } = team.derivedSettings;
+
+      if (!aiFeaturesEnabled) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'AI features are not enabled for this team',
+        });
+      }
+
+      if (!IS_AI_FEATURES_CONFIGURED()) {
+        throw new AppError(AppErrorCode.INVALID_REQUEST, {
+          message: 'AI features are not configured. Please contact support to enable AI features.',
+        });
+      }
+
+      logger.info({
+        event: 'ai.detect-fields.start',
+        envelopeId,
+        userId: session.user.id,
+        teamId: team.id,
+        hasContext: !!context,
+      });
+
+      // Return streaming response with NDJSON
+      return streamText(c, async (stream) => {
+        // Start keepalive to prevent connection timeout
+        let interval: NodeJS.Timeout | null = setInterval(() => {
+          void stream.writeln(JSON.stringify({ type: 'keepalive' }));
+        }, KEEPALIVE_INTERVAL_MS);
+
+        try {
+          const allFields = await detectFieldsFromEnvelope({
+            context,
+            envelopeId,
+            userId: session.user.id,
+            teamId: team.id,
+            onProgress: (progress) => {
+              void stream.writeln(
+                JSON.stringify({
+                  type: 'progress',
+                  pagesProcessed: progress.pagesProcessed,
+                  totalPages: progress.totalPages,
+                  fieldsDetected: progress.fieldsDetected,
+                }),
+              );
+            },
+          });
+
+          // Clear keepalive before sending final response
+          if (interval) {
+            clearInterval(interval);
+            interval = null;
+          }
+
+          logger.info({
+            event: 'ai.detect-fields.complete',
+            envelopeId,
+            userId: session.user.id,
+            teamId: team.id,
+            fieldCount: allFields.length,
+          });
+
+          await stream.writeln(
+            JSON.stringify({
+              type: 'complete',
+              fields: allFields,
+            }),
+          );
+        } catch (error) {
+          // Clear keepalive on error
+          if (interval) {
+            clearInterval(interval);
+          }
+
+          // The logger below it stringifies the error, using `console.error`
+          // to attempt to get a stack trace
+          console.error(error);
+
+          logger.error({
+            event: 'ai.detect-fields.error',
+            error,
+          });
+
+          const message = error instanceof AppError ? error.message : 'Failed to detect fields';
+
+          await stream.writeln(
+            JSON.stringify({
+              type: 'error',
+              message,
+            }),
+          );
+        }
+      });
+    } catch (error) {
+      // Handle errors that occur before streaming starts
+      logger.error({
+        event: 'ai.detect-fields.error',
+        error,
+      });
+
+      if (error instanceof AppError) {
+        const { status, body } = AppError.toRestAPIError(error);
+
+        return c.json(body, status);
+      }
+
+      return c.json({ error: 'Failed to detect fields' }, 500);
+    }
+  },
+);

apps/remix/server/api/ai/detect-fields.types.ts

@@ -0,0 +1,54 @@
+import { z } from 'zod';
+
+import {
+  ZConfidenceLevel,
+  ZDetectableFieldType,
+} from '@documenso/lib/server-only/ai/envelope/detect-fields/schema';
+
+export const ZDetectFieldsRequestSchema = z.object({
+  envelopeId: z.string().min(1).describe('The ID of the envelope to detect fields from.'),
+  teamId: z.number().describe('The ID of the team the envelope belongs to.'),
+  context: z
+    .string()
+    .optional()
+    .describe(
+      'Optional context about recipients to help map fields (e.g., "David is the Employee, Lucas is the Manager").',
+    ),
+});
+
+export type TDetectFieldsRequest = z.infer<typeof ZDetectFieldsRequestSchema>;
+
+// Schema for fields returned from streaming API (before recipient resolution)
+export const ZNormalizedFieldWithPageSchema = z.object({
+  type: ZDetectableFieldType,
+  recipientKey: z.string(),
+  positionX: z.number(),
+  positionY: z.number(),
+  width: z.number(),
+  height: z.number(),
+  confidence: ZConfidenceLevel,
+  pageNumber: z.number(),
+});
+
+export type TNormalizedFieldWithPage = z.infer<typeof ZNormalizedFieldWithPageSchema>;
+
+// Schema for fields after recipient resolution
+export const ZNormalizedFieldWithContextSchema = z.object({
+  type: ZDetectableFieldType,
+  positionX: z.number(),
+  positionY: z.number(),
+  width: z.number(),
+  height: z.number(),
+  confidence: ZConfidenceLevel,
+  pageNumber: z.number(),
+  recipientId: z.number(),
+  envelopeItemId: z.string(),
+});
+
+export type TNormalizedFieldWithContext = z.infer<typeof ZNormalizedFieldWithContextSchema>;
+
+export const ZDetectFieldsResponseSchema = z.object({
+  fields: z.array(ZNormalizedFieldWithContextSchema),
+});
+
+export type TDetectFieldsResponse = z.infer<typeof ZDetectFieldsResponseSchema>;

apps/remix/server/api/ai/detect-recipients.client.ts

@@ -0,0 +1,160 @@
+import { z } from 'zod';
+
+import { ZDetectedRecipientSchema } from '@documenso/lib/server-only/ai/envelope/detect-recipients/schema';
+
+import { type TDetectRecipientsRequest } from './detect-recipients.types';
+
+export type { TDetectRecipientsRequest };
+
+// Stream event schemas
+const ZProgressEventSchema = z.object({
+  type: z.literal('progress'),
+  pagesProcessed: z.number(),
+  totalPages: z.number(),
+  recipientsDetected: z.number(),
+});
+
+const ZKeepaliveEventSchema = z.object({
+  type: z.literal('keepalive'),
+});
+
+const ZErrorEventSchema = z.object({
+  type: z.literal('error'),
+  message: z.string(),
+});
+
+const ZCompleteEventSchema = z.object({
+  type: z.literal('complete'),
+  recipients: z.array(ZDetectedRecipientSchema),
+});
+
+const ZStreamEventSchema = z.discriminatedUnion('type', [
+  ZProgressEventSchema,
+  ZKeepaliveEventSchema,
+  ZErrorEventSchema,
+  ZCompleteEventSchema,
+]);
+
+export type DetectRecipientsProgressEvent = z.infer<typeof ZProgressEventSchema>;
+export type DetectRecipientsCompleteEvent = z.infer<typeof ZCompleteEventSchema>;
+export type DetectRecipientsStreamEvent = z.infer<typeof ZStreamEventSchema>;
+
+const ZApiErrorResponseSchema = z.object({
+  error: z.string(),
+});
+
+export class AiApiError extends Error {
+  constructor(
+    message: string,
+    public status: number,
+  ) {
+    super(message);
+    this.name = 'AiApiError';
+  }
+}
+
+export type DetectRecipientsOptions = {
+  request: TDetectRecipientsRequest;
+  onProgress?: (event: DetectRecipientsProgressEvent) => void;
+  onComplete: (event: DetectRecipientsCompleteEvent) => void;
+  onError: (error: AiApiError) => void;
+  signal?: AbortSignal;
+};
+
+/**
+ * Detect recipients from an envelope using AI with streaming support.
+ */
+export const detectRecipients = async ({
+  request,
+  onProgress,
+  onComplete,
+  onError,
+  signal,
+}: DetectRecipientsOptions): Promise<void> => {
+  const response = await fetch('/api/ai/detect-recipients', {
+    method: 'POST',
+    headers: {
+      'Content-Type': 'application/json',
+    },
+    body: JSON.stringify(request),
+    signal,
+  });
+
+  // Handle non-streaming error responses (auth failures, etc.)
+  if (!response.ok) {
+    const text = await response.text();
+
+    try {
+      const parsed = ZApiErrorResponseSchema.parse(JSON.parse(text));
+
+      throw new AiApiError(parsed.error, response.status);
+    } catch (e) {
+      if (e instanceof AiApiError) {
+        throw e;
+      }
+
+      throw new AiApiError('Failed to detect recipients', response.status);
+    }
+  }
+
+  // Handle streaming response
+  const reader = response.body?.getReader();
+
+  if (!reader) {
+    throw new AiApiError('No response body', 500);
+  }
+
+  const decoder = new TextDecoder();
+  let buffer = '';
+
+  try {
+    let done = false;
+
+    while (!done) {
+      const result = await reader.read();
+      done = result.done;
+
+      if (done) {
+        break;
+      }
+
+      const value = result.value;
+
+      buffer += decoder.decode(value, { stream: true });
+
+      // Process complete lines
+      const lines = buffer.split('\n');
+      buffer = lines.pop() || ''; // Keep incomplete line in buffer
+
+      for (const line of lines) {
+        if (!line.trim()) {
+          continue;
+        }
+
+        try {
+          const event = ZStreamEventSchema.parse(JSON.parse(line));
+
+          switch (event.type) {
+            case 'progress':
+              onProgress?.(event);
+              break;
+            case 'keepalive':
+              // Ignore keepalive, it's just to prevent timeout
+              break;
+            case 'error':
+              onError(new AiApiError(event.message, 500));
+              return;
+            case 'complete':
+              onComplete(event);
+              return;
+          }
+        } catch {
+          // Ignore malformed lines
+          console.warn('Failed to parse stream event:', line);
+        }
+      }
+    }
+  } finally {
+    reader.releaseLock();
+  }
+};

apps/remix/server/api/ai/detect-recipients.ts

@@ -0,0 +1,152 @@
+import { sValidator } from '@hono/standard-validator';
+import { Hono } from 'hono';
+import { streamText } from 'hono/streaming';
+
+import { getSession } from '@documenso/auth/server/lib/utils/get-session';
+import { IS_AI_FEATURES_CONFIGURED } from '@documenso/lib/constants/app';
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { detectRecipientsFromEnvelope } from '@documenso/lib/server-only/ai/envelope/detect-recipients';
+import { getTeamById } from '@documenso/lib/server-only/team/get-team';
+
+import type { HonoEnv } from '../../router';
+import { ZDetectRecipientsRequestSchema } from './detect-recipients.types';
+
+const KEEPALIVE_INTERVAL_MS = 5000;
+
+export const detectRecipientsRoute = new Hono<HonoEnv>().post(
+  '/',
+  sValidator('json', ZDetectRecipientsRequestSchema),
+  async (c) => {
+    const logger = c.get('logger');
+
+    try {
+      const { envelopeId, teamId } = c.req.valid('json');
+
+      const session = await getSession(c);
+
+      if (!session.user) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'You must be logged in to detect recipients',
+        });
+      }
+
+      // Verify user has access to the team (abort early)
+      const team = await getTeamById({
+        userId: session.user.id,
+        teamId,
+      }).catch(() => null);
+
+      if (!team) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'You do not have access to this team',
+        });
+      }
+
+      // Check if AI features are enabled for the team
+      const { aiFeaturesEnabled } = team.derivedSettings;
+
+      if (!aiFeaturesEnabled) {
+        throw new AppError(AppErrorCode.UNAUTHORIZED, {
+          message: 'AI features are not enabled for this team',
+        });
+      }
+
+      if (!IS_AI_FEATURES_CONFIGURED()) {
+        throw new AppError(AppErrorCode.INVALID_REQUEST, {
+          message: 'AI features are not configured. Please contact support to enable AI features.',
+        });
+      }
+
+      logger.info({
+        event: 'ai.detect-recipients.start',
+        envelopeId,
+        userId: session.user.id,
+        teamId: team.id,
+      });
+
+      // Return streaming response with NDJSON
+      return streamText(c, async (stream) => {
+        // Start keepalive to prevent connection timeout
+        let interval: NodeJS.Timeout | null = setInterval(() => {
+          void stream.writeln(JSON.stringify({ type: 'keepalive' }));
+        }, KEEPALIVE_INTERVAL_MS);
+
+        try {
+          const recipients = await detectRecipientsFromEnvelope({
+            envelopeId,
+            userId: session.user.id,
+            teamId: team.id,
+            onProgress: (progress) => {
+              void stream.writeln(
+                JSON.stringify({
+                  type: 'progress',
+                  pagesProcessed: progress.pagesProcessed,
+                  totalPages: progress.totalPages,
+                  recipientsDetected: progress.recipientsDetected,
+                }),
+              );
+            },
+          });
+
+          // Clear keepalive before sending final response
+          if (interval) {
+            clearInterval(interval);
+            interval = null;
+          }
+
+          logger.info({
+            event: 'ai.detect-recipients.complete',
+            envelopeId,
+            userId: session.user.id,
+            teamId: team.id,
+            recipientCount: recipients.length,
+          });
+
+          await stream.writeln(
+            JSON.stringify({
+              type: 'complete',
+              recipients,
+            }),
+          );
+        } catch (error) {
+          // Clear keepalive on error
+          if (interval) {
+            clearInterval(interval);
+          }
+
+          // The logger below it stringifies the error, using `console.error`
+          // to attempt to get a stack trace
+          console.error(error);
+
+          logger.error({
+            event: 'ai.detect-recipients.error',
+            error,
+          });
+
+          const message = error instanceof AppError ? error.message : 'Failed to detect recipients';
+
+          await stream.writeln(
+            JSON.stringify({
+              type: 'error',
+              message,
+            }),
+          );
+        }
+      });
+    } catch (error) {
+      // Handle errors that occur before streaming starts
+      logger.error({
+        event: 'ai.detect-recipients.error',
+        error,
+      });
+
+      if (error instanceof AppError) {
+        const { status, body } = AppError.toRestAPIError(error);
+
+        return c.json(body, status);
+      }
+
+      return c.json({ error: 'Failed to detect recipients' }, 500);
+    }
+  },
+);

apps/remix/server/api/ai/detect-recipients.types.ts

@@ -0,0 +1,16 @@
+import { z } from 'zod';
+
+import { ZDetectedRecipientSchema } from '@documenso/lib/server-only/ai/envelope/detect-recipients/schema';
+
+export const ZDetectRecipientsRequestSchema = z.object({
+  envelopeId: z.string().min(1).describe('The ID of the envelope to detect recipients from.'),
+  teamId: z.number().describe('The ID of the team the envelope belongs to.'),
+});
+
+export type TDetectRecipientsRequest = z.infer<typeof ZDetectRecipientsRequestSchema>;
+
+export const ZDetectRecipientsResponseSchema = z.object({
+  recipients: z.array(ZDetectedRecipientSchema),
+});
+
+export type TDetectRecipientsResponse = z.infer<typeof ZDetectRecipientsResponseSchema>;

apps/remix/server/api/ai/route.ts

@@ -0,0 +1,9 @@
+import { Hono } from 'hono';
+
+import type { HonoEnv } from '../../router';
+import { detectFieldsRoute } from './detect-fields';
+import { detectRecipientsRoute } from './detect-recipients';
+
+export const aiRoute = new Hono<HonoEnv>()
+  .route('/detect-recipients', detectRecipientsRoute)
+  .route('/detect-fields', detectFieldsRoute);

apps/remix/server/router.ts

@@ -12,9 +12,11 @@ import { API_V2_BETA_URL, API_V2_URL } from '@documenso/lib/constants/app';
 import { jobsClient } from '@documenso/lib/jobs/client';
 import { TelemetryClient } from '@documenso/lib/server-only/telemetry/telemetry-client';
 import { getIpAddress } from '@documenso/lib/universal/get-ip-address';
+import { env } from '@documenso/lib/utils/env';
 import { logger } from '@documenso/lib/utils/logger';
 import { openApiDocument } from '@documenso/trpc/server/open-api';
 
+import { aiRoute } from './api/ai/route';
 import { downloadRoute } from './api/download/download';
 import { filesRoute } from './api/files/files';
 import { type AppContext, appContext } from './context';
@@ -50,6 +52,21 @@ const rateLimitMiddleware = rateLimiter({
   },
 });
 
+const aiRateLimitMiddleware = rateLimiter({
+  windowMs: 60 * 1000, // 1 minute
+  limit: 3, // 3 requests per window
+  keyGenerator: (c) => {
+    try {
+      return getIpAddress(c.req.raw);
+    } catch (error) {
+      return 'unknown';
+    }
+  },
+  message: {
+    error: 'Too many requests, please try again later.',
+  },
+});
+
 /**
  * Attach session and context to requests.
  */
@@ -85,6 +102,10 @@ app.route('/api/auth', auth);
 // Files route.
 app.route('/api/files', filesRoute);
 
+// AI route.
+app.use('/api/ai/*', aiRateLimitMiddleware);
+app.route('/api/ai', aiRoute);
+
 // API servers.
 app.use(`/api/v1/*`, cors());
 app.route('/api/v1', tsRestHonoApp);
@@ -115,6 +136,8 @@ app.use(`${API_V2_BETA_URL}/*`, async (c) =>
 
 // Start telemetry client for anonymous usage tracking.
 // Can be disabled by setting DOCUMENSO_DISABLE_TELEMETRY=true
-void TelemetryClient.start();
+if (env('NODE_ENV') !== 'development') {
+  void TelemetryClient.start();
+}
 
 export default app;

apps/remix/vite.config.ts

@@ -51,6 +51,7 @@ export default defineConfig({
   ssr: {
     noExternal: ['react-dropzone', 'plausible-tracker'],
     external: [
+      '@napi-rs/canvas',
       '@node-rs/bcrypt',
       '@prisma/client',
       '@documenso/tailwind-config',
@@ -64,6 +65,7 @@ export default defineConfig({
     include: ['prop-types', 'file-selector', 'attr-accept'],
     exclude: [
       'node_modules',
+      '@napi-rs/canvas',
       '@node-rs/bcrypt',
       '@documenso/pdf-sign',
       'sharp',
@@ -94,6 +96,7 @@ export default defineConfig({
   build: {
     rollupOptions: {
       external: [
+        '@napi-rs/canvas',
         '@node-rs/bcrypt',
         '@documenso/pdf-sign',
         '@aws-sdk/cloudfront-signer',

docker/Dockerfile

@@ -70,6 +70,7 @@ COPY --from=builder /app/out/json/ .
 COPY --from=builder /app/out/package-lock.json ./package-lock.json
 
 COPY --from=builder /app/lingui.config.ts ./lingui.config.ts
+COPY --from=builder /app/patches ./patches
 
 RUN npm ci
 
@@ -108,6 +109,8 @@ WORKDIR /app
 COPY --from=builder --chown=nodejs:nodejs /app/out/json/ .
 # Copy the tailwind config files across
 COPY --from=builder --chown=nodejs:nodejs /app/out/full/packages/tailwind-config ./packages/tailwind-config
+# Copy the patches across
+COPY --from=builder --chown=nodejs:nodejs /app/patches ./patches
 
 RUN npm ci --only=production
 

package.json

@@ -5,8 +5,9 @@
     "apps/*",
     "packages/*"
   ],
-  "version": "2.1.0",
+  "version": "2.2.5",
   "scripts": {
+    "postinstall": "patch-package",
     "build": "turbo run build",
     "dev": "turbo run dev --filter=@documenso/remix",
     "dev:remix": "turbo run dev --filter=@documenso/remix",
@@ -63,7 +64,7 @@
     "lint-staged": "^16.2.7",
     "nanoid": "^5.1.6",
     "nodemailer": "^7.0.10",
-    "pdfjs-dist": "5.4.296",
+    "pdfjs-dist": "5.4.449",
     "pino": "^9.14.0",
     "pino-pretty": "^13.1.2",
     "playwright": "1.56.1",
@@ -83,19 +84,22 @@
     "zod-prisma-types": "3.3.5"
   },
   "dependencies": {
+    "@ai-sdk/google-vertex": "3.0.81",
     "@documenso/pdf-sign": "^0.1.0",
     "@documenso/prisma": "*",
     "@lingui/conf": "^5.6.0",
     "@lingui/core": "^5.6.0",
+    "ai": "^5.0.104",
     "inngest-cli": "^1.13.7",
     "luxon": "^3.7.2",
+    "patch-package": "^8.0.1",
     "posthog-node": "4.18.0",
     "react": "^18",
     "typescript": "5.6.2",
     "zod": "^3.25.76"
   },
   "overrides": {
-    "pdfjs-dist": "5.4.296",
+    "pdfjs-dist": "5.4.449",
     "typescript": "5.6.2",
     "zod": "^3.25.76"
   }

packages/app-tests/e2e/api/v2/embedding-presign.spec.ts

@@ -1,6 +1,9 @@
 import { expect, test } from '@playwright/test';
+import type { APIRequestContext } from 'playwright-core';
 
 import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
+import type { CreateEmbeddingPresignTokenOptions } from '@documenso/lib/server-only/embedding-presign/create-embedding-presign-token';
+import type { VerifyEmbeddingPresignTokenOptions } from '@documenso/lib/server-only/embedding-presign/verify-embedding-presign-token';
 import { createApiToken } from '@documenso/lib/server-only/public-api/create-api-token';
 import { seedUser } from '@documenso/prisma/seed/users';
 
@@ -17,18 +20,7 @@ test.describe('Embedding Presign API', () => {
       expiresIn: null,
     });
 
-    const response = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/create-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          apiToken: token,
-        },
-      },
-    );
+    const response = await createPresignToken(request, token);
 
     const responseData = await response.json();
 
@@ -54,19 +46,9 @@ test.describe('Embedding Presign API', () => {
       expiresIn: null,
     });
 
-    const response = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/create-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          apiToken: token,
-          expiresIn: 120, // 2 hours
-        },
-      },
-    );
+    const response = await createPresignToken(request, token, {
+      expiresIn: 120, // 2 hours
+    });
 
     const responseData = await response.json();
 
@@ -92,19 +74,9 @@ test.describe('Embedding Presign API', () => {
       expiresIn: null,
     });
 
-    const response = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/create-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          apiToken: token,
-          expiresIn: 0, // Immediate expiration
-        },
-      },
-    );
+    const response = await createPresignToken(request, token, {
+      expiresIn: 0, // Immediate expiration
+    });
 
     expect(response.ok()).toBeTruthy();
     expect(response.status()).toBe(200);
@@ -129,18 +101,7 @@ test.describe('Embedding Presign API', () => {
     });
 
     // First create a token
-    const createResponse = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/create-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          apiToken: token,
-        },
-      },
-    );
+    const createResponse = await createPresignToken(request, token);
 
     expect(createResponse.ok()).toBeTruthy();
     const createResponseData = await createResponse.json();
@@ -150,18 +111,9 @@ test.describe('Embedding Presign API', () => {
     const presignToken = createResponseData.token;
 
     // Then verify it
-    const verifyResponse = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/verify-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          token: presignToken,
-        },
-      },
-    );
+    const verifyResponse = await verifyPresignToken(request, token, {
+      token: presignToken,
+    });
 
     expect(verifyResponse.ok()).toBeTruthy();
     expect(verifyResponse.status()).toBe(200);
@@ -183,18 +135,87 @@ test.describe('Embedding Presign API', () => {
       expiresIn: null,
     });
 
-    const response = await request.post(
-      `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/verify-presign-token`,
-      {
-        headers: {
-          Authorization: `Bearer ${token}`,
-          'Content-Type': 'application/json',
-        },
-        data: {
-          token: 'invalid-token',
-        },
-      },
-    );
+    const response = await verifyPresignToken(request, token, {
+      token: 'invalid-token',
+    });
+
+    const responseData = await response.json();
+
+    console.log('Invalid token response:', responseData);
+
+    expect(response.ok()).toBeTruthy();
+    expect(response.status()).toBe(200);
+
+    expect(responseData.success).toBe(false);
+  });
+
+  test('verifyEmbeddingPresignToken: should verify a valid scoped token', async ({ request }) => {
+    const { user, team } = await seedUser();
+
+    const { token } = await createApiToken({
+      userId: user.id,
+      teamId: team.id,
+      tokenName: 'test',
+      expiresIn: null,
+    });
+
+    // First create a token
+    const createResponse = await createPresignToken(request, token, {
+      scope: 'documentId:1',
+    });
+
+    expect(createResponse.ok()).toBeTruthy();
+    const createResponseData = await createResponse.json();
+
+    console.log('Create response:', createResponseData);
+
+    const presignToken = createResponseData.token;
+
+    // Then verify it
+    const verifyResponse = await verifyPresignToken(request, token, {
+      token: presignToken,
+      scope: 'documentId:1',
+    });
+
+    expect(verifyResponse.ok()).toBeTruthy();
+    expect(verifyResponse.status()).toBe(200);
+
+    const verifyResponseData = await verifyResponse.json();
+
+    console.log('Verify response:', verifyResponseData);
+
+    expect(verifyResponseData.success).toBe(true);
+  });
+
+  test('verifyEmbeddingPresignToken: should reject a scope mismatched token', async ({
+    request,
+  }) => {
+    const { user, team } = await seedUser();
+
+    const { token } = await createApiToken({
+      userId: user.id,
+      teamId: team.id,
+      tokenName: 'test',
+      expiresIn: null,
+    });
+
+    // First create a token
+    const createResponse = await createPresignToken(request, token, {
+      scope: 'documentId:1',
+    });
+
+    expect(createResponse.ok()).toBeTruthy();
+    const createResponseData = await createResponse.json();
+
+    console.log('Create response:', createResponseData);
+
+    const presignToken = createResponseData.token;
+
+    // Then verify it
+    const response = await verifyPresignToken(request, token, {
+      token: presignToken,
+      scope: 'documentId:2',
+    });
 
     const responseData = await response.json();
 
@@ -206,3 +227,40 @@ test.describe('Embedding Presign API', () => {
     expect(responseData.success).toBe(false);
   });
 });
+
+const createPresignToken = async (
+  request: APIRequestContext,
+  apiToken: string,
+  data?: Partial<CreateEmbeddingPresignTokenOptions>,
+) => {
+  return await request.post(
+    `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/create-presign-token`,
+    {
+      headers: {
+        Authorization: `Bearer ${apiToken}`,
+        'Content-Type': 'application/json',
+      },
+      data: {
+        apiToken,
+        ...data,
+      },
+    },
+  );
+};
+
+const verifyPresignToken = async (
+  request: APIRequestContext,
+  apiToken: string,
+  data: VerifyEmbeddingPresignTokenOptions,
+) => {
+  return await request.post(
+    `${NEXT_PUBLIC_WEBAPP_URL()}/api/v2-beta/embedding/verify-presign-token`,
+    {
+      headers: {
+        Authorization: `Bearer ${apiToken}`,
+        'Content-Type': 'application/json',
+      },
+      data,
+    },
+  );
+};

packages/app-tests/e2e/api/v2/envelopes-api.spec.ts

@@ -6,6 +6,7 @@ import { pick } from 'remeda';
 
 import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
 import { createApiToken } from '@documenso/lib/server-only/public-api/create-api-token';
+import { DocumentAccessAuth } from '@documenso/lib/types/document-auth';
 import { prisma } from '@documenso/prisma';
 import {
   DocumentDistributionMethod,
@@ -23,7 +24,9 @@ import type {
   TCreateEnvelopePayload,
   TCreateEnvelopeResponse,
 } from '@documenso/trpc/server/envelope-router/create-envelope.types';
+import type { TDistributeEnvelopeRequest } from '@documenso/trpc/server/envelope-router/distribute-envelope.types';
 import type { TCreateEnvelopeRecipientsRequest } from '@documenso/trpc/server/envelope-router/envelope-recipients/create-envelope-recipients.types';
+import type { TUpdateEnvelopeRecipientsRequest } from '@documenso/trpc/server/envelope-router/envelope-recipients/update-envelope-recipients.types';
 import type { TGetEnvelopeResponse } from '@documenso/trpc/server/envelope-router/get-envelope.types';
 import type { TUpdateEnvelopeRequest } from '@documenso/trpc/server/envelope-router/update-envelope.types';
 
@@ -144,6 +147,9 @@ test.describe('API V2 Envelopes', () => {
         externalId: 'externalId',
         visibility: DocumentVisibility.MANAGER_AND_ABOVE,
         globalAccessAuth: ['ACCOUNT'],
+        // Ignore this error in the test since it doesn't actually exist in the PDF:
+        // - Error setting value for field hello: PDFDocument has no form field with the name "hello"
+        // We want to check if the form value is set in the DB.
         formValues: {
           hello: 'world',
         },
@@ -262,8 +268,6 @@ test.describe('API V2 Envelopes', () => {
         },
       });
 
-      console.log(userB.email);
-
       expect(envelope.envelopeItems.length).toBe(2);
       expect(envelope.envelopeItems[0].title).toBe('field-meta.pdf');
       expect(envelope.envelopeItems[1].title).toBe('field-font-alignment.pdf');
@@ -557,4 +561,543 @@ test.describe('API V2 Envelopes', () => {
       userEmail: userA.email,
     });
   });
+
+  test.describe('Empty recipient tests', () => {
+    test('Create template envelope with empty email recipient', async ({ request }) => {
+      const payload = {
+        type: EnvelopeType.TEMPLATE,
+        title: 'Template with Empty Email Recipient',
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const res = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(res.ok()).toBeTruthy();
+      expect(res.status()).toBe(200);
+
+      const response = (await res.json()) as TCreateEnvelopeResponse;
+
+      // Create recipient with empty email
+      const createRecipientsRequest: TCreateEnvelopeRecipientsRequest = {
+        envelopeId: response.id,
+        data: [
+          {
+            email: '',
+            name: 'Test Recipient',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+        ],
+      };
+
+      const createRecipientsRes = await request.post(`${baseUrl}/envelope/recipient/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createRecipientsRequest,
+      });
+
+      expect(createRecipientsRes.ok()).toBeTruthy();
+      expect(createRecipientsRes.status()).toBe(200);
+
+      const recipientsResponse = await createRecipientsRes.json();
+      const recipient = recipientsResponse.data[0];
+
+      expect(recipient.email).toBe('');
+      expect(recipient.name).toBe('Test Recipient');
+
+      // Get envelope items to assign fields
+      const getEnvelopeRes = await request.get(`${baseUrl}/envelope/${response.id}`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+      });
+
+      const envelope: TGetEnvelopeResponse = await getEnvelopeRes.json();
+      const envelopeItem = envelope.envelopeItems[0];
+
+      // Create field for the recipient with empty email
+      const createFieldsRequest = {
+        envelopeId: response.id,
+        data: [
+          {
+            recipientId: recipient.id,
+            envelopeItemId: envelopeItem.id,
+            type: FieldType.SIGNATURE,
+            page: 1,
+            positionX: 100,
+            positionY: 100,
+            width: 50,
+            height: 50,
+          },
+        ],
+      };
+
+      const createFieldsRes = await request.post(`${baseUrl}/envelope/field/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createFieldsRequest,
+      });
+
+      expect(createFieldsRes.ok()).toBeTruthy();
+      expect(createFieldsRes.status()).toBe(200);
+    });
+
+    test('Create document envelope with empty email recipient', async ({ request }) => {
+      const payload = {
+        type: EnvelopeType.DOCUMENT,
+        title: 'Document with Empty Email Recipient',
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const res = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(res.ok()).toBeTruthy();
+      expect(res.status()).toBe(200);
+
+      const response = (await res.json()) as TCreateEnvelopeResponse;
+
+      // Create recipient with empty email
+      const createRecipientsRequest: TCreateEnvelopeRecipientsRequest = {
+        envelopeId: response.id,
+        data: [
+          {
+            email: '',
+            name: 'Document Recipient No Email',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+        ],
+      };
+
+      const createRecipientsRes = await request.post(`${baseUrl}/envelope/recipient/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createRecipientsRequest,
+      });
+
+      expect(createRecipientsRes.ok()).toBeTruthy();
+      const recipientsResponse = await createRecipientsRes.json();
+      const recipient = recipientsResponse.data[0];
+
+      expect(recipient.email).toBe('');
+      expect(recipient.name).toBe('Document Recipient No Email');
+    });
+
+    test('Update recipient to have empty email', async ({ request }) => {
+      const payload = {
+        type: EnvelopeType.TEMPLATE,
+        title: 'Update Recipient Email Test',
+        recipients: [
+          {
+            email: userA.email,
+            name: 'Test User',
+            role: RecipientRole.SIGNER,
+          },
+        ],
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const createRes = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(createRes.ok()).toBeTruthy();
+      const createResponse = (await createRes.json()) as TCreateEnvelopeResponse;
+
+      // Get the envelope to get recipient ID
+      const getRes = await request.get(`${baseUrl}/envelope/${createResponse.id}`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+      });
+
+      const envelope: TGetEnvelopeResponse = await getRes.json();
+      const recipientId = envelope.recipients[0].id;
+
+      // Update recipient to have empty email
+      const updateRequest: TUpdateEnvelopeRecipientsRequest = {
+        envelopeId: createResponse.id,
+        data: [
+          {
+            id: recipientId,
+            email: '',
+            name: 'Updated Name No Email',
+          },
+        ],
+      };
+
+      const updateRes = await request.post(`${baseUrl}/envelope/recipient/update-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: updateRequest,
+      });
+
+      expect(updateRes.ok()).toBeTruthy();
+      const updateResponse = await updateRes.json();
+      const updatedRecipient = updateResponse.data[0];
+
+      expect(updatedRecipient.email).toBe('');
+      expect(updatedRecipient.name).toBe('Updated Name No Email');
+    });
+
+    test('Mixed recipients with and without emails', async ({ request }) => {
+      const payload = {
+        type: EnvelopeType.TEMPLATE,
+        title: 'Mixed Recipients Test',
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const res = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(res.ok()).toBeTruthy();
+      const response = (await res.json()) as TCreateEnvelopeResponse;
+
+      // Create multiple recipients, some with email, some without
+      const createRecipientsRequest: TCreateEnvelopeRecipientsRequest = {
+        envelopeId: response.id,
+        data: [
+          {
+            email: userA.email,
+            name: 'Recipient With Email',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+          {
+            email: '',
+            name: 'Recipient Without Email 1',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+          {
+            email: userB.email,
+            name: 'Another With Email',
+            role: RecipientRole.APPROVER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+          {
+            email: '',
+            name: 'Recipient Without Email 2',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+        ],
+      };
+
+      const createRecipientsRes = await request.post(`${baseUrl}/envelope/recipient/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createRecipientsRequest,
+      });
+
+      expect(createRecipientsRes.ok()).toBeTruthy();
+      const recipientsResponse = await createRecipientsRes.json();
+      const recipients = recipientsResponse.data;
+
+      expect(recipients.length).toBe(4);
+      expect(recipients[0].email).toBe(userA.email.toLowerCase());
+      expect(recipients[1].email).toBe('');
+      expect(recipients[2].email).toBe(userB.email.toLowerCase());
+      expect(recipients[3].email).toBe('');
+
+      // Get envelope to assign fields
+      const getEnvelopeRes = await request.get(`${baseUrl}/envelope/${response.id}`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+      });
+
+      const envelope: TGetEnvelopeResponse = await getEnvelopeRes.json();
+      const envelopeItem = envelope.envelopeItems[0];
+
+      // Create fields for all recipients including those without emails
+      const createFieldsRequest = {
+        envelopeId: response.id,
+        data: recipients.map((recipient, index) => ({
+          recipientId: recipient.id,
+          envelopeItemId: envelopeItem.id,
+          type: FieldType.SIGNATURE,
+          page: 1,
+          positionX: 100,
+          positionY: 0 + index,
+          width: 50,
+          height: 50,
+        })),
+      };
+
+      const createFieldsRes = await request.post(`${baseUrl}/envelope/field/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createFieldsRequest,
+      });
+
+      expect(createFieldsRes.ok()).toBeTruthy();
+    });
+
+    test('Distribute envelope with empty email recipients', async ({ request }) => {
+      const payload = {
+        type: EnvelopeType.DOCUMENT,
+        title: 'Document for Distribution with Empty Email',
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const createRes = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(createRes.ok()).toBeTruthy();
+      const createResponse = (await createRes.json()) as TCreateEnvelopeResponse;
+
+      // Create recipients with empty emails
+      const createRecipientsRequest: TCreateEnvelopeRecipientsRequest = {
+        envelopeId: createResponse.id,
+        data: [
+          {
+            email: '',
+            name: 'Recipient One',
+            role: RecipientRole.SIGNER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+          {
+            email: '',
+            name: 'Recipient Two',
+            role: RecipientRole.APPROVER,
+            accessAuth: [],
+            actionAuth: [],
+          },
+        ],
+      };
+
+      const createRecipientsRes = await request.post(`${baseUrl}/envelope/recipient/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createRecipientsRequest,
+      });
+
+      expect(createRecipientsRes.ok()).toBeTruthy();
+      const recipientsResponse = await createRecipientsRes.json();
+      const recipients = recipientsResponse.data;
+
+      // Get envelope to assign fields
+      const getEnvelopeRes = await request.get(`${baseUrl}/envelope/${createResponse.id}`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+      });
+
+      const envelope: TGetEnvelopeResponse = await getEnvelopeRes.json();
+      const envelopeItem = envelope.envelopeItems[0];
+
+      // Create fields for recipients
+      const createFieldsRequest = {
+        envelopeId: createResponse.id,
+        data: recipients.map((recipient, index) => ({
+          recipientId: recipient.id,
+          envelopeItemId: envelopeItem.id,
+          type: FieldType.SIGNATURE,
+          page: 1,
+          positionX: 100,
+          positionY: 0 + index,
+          width: 50,
+          height: 50,
+        })),
+      };
+
+      const createFieldsRes = await request.post(`${baseUrl}/envelope/field/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createFieldsRequest,
+      });
+
+      expect(createFieldsRes.ok()).toBeTruthy();
+
+      // Distribute the envelope
+      const distributeRes = await request.post(`${baseUrl}/envelope/distribute`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: {
+          envelopeId: createResponse.id,
+        } satisfies TDistributeEnvelopeRequest,
+      });
+
+      expect(distributeRes.ok()).toBeTruthy();
+      expect(distributeRes.status()).toBe(200);
+
+      const distributeResponse = await distributeRes.json();
+      expect(distributeResponse.success).toBe(true);
+      expect(distributeResponse.id).toBe(createResponse.id);
+      expect(distributeResponse.recipients).toHaveLength(2);
+
+      // Verify recipients have empty emails and signing URLs
+      expect(distributeResponse.recipients[0].email).toBe('');
+      expect(distributeResponse.recipients[0].signingUrl).toBeTruthy();
+      expect(distributeResponse.recipients[1].email).toBe('');
+      expect(distributeResponse.recipients[1].signingUrl).toBeTruthy();
+    });
+
+    test('Distribute envelope with empty email recipient and auth requirements fails', async ({
+      request,
+    }) => {
+      const payload = {
+        type: EnvelopeType.DOCUMENT,
+        title: 'Document with Auth Requirements',
+      } satisfies TCreateEnvelopePayload;
+
+      const formData = new FormData();
+      formData.append('payload', JSON.stringify(payload));
+
+      const files = [
+        {
+          name: 'example.pdf',
+          data: fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf')),
+        },
+      ];
+
+      for (const file of files) {
+        formData.append('files', new File([file.data], file.name, { type: 'application/pdf' }));
+      }
+
+      const createRes = await request.post(`${baseUrl}/envelope/create`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        multipart: formData,
+      });
+
+      expect(createRes.ok()).toBeTruthy();
+      const createResponse = (await createRes.json()) as TCreateEnvelopeResponse;
+
+      // Create recipient with empty email and TWO_FACTOR_AUTH action auth
+      const createRecipientsRequest: TCreateEnvelopeRecipientsRequest = {
+        envelopeId: createResponse.id,
+        data: [
+          {
+            email: '',
+            name: 'Recipient With Auth',
+            role: RecipientRole.SIGNER,
+            accessAuth: [DocumentAccessAuth.TWO_FACTOR_AUTH],
+          },
+        ],
+      };
+
+      const createRecipientsRes = await request.post(`${baseUrl}/envelope/recipient/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createRecipientsRequest,
+      });
+
+      expect(createRecipientsRes.ok()).toBeTruthy();
+      const recipientsResponse = await createRecipientsRes.json();
+      const recipient = recipientsResponse.data[0];
+
+      // Get envelope to assign fields
+      const getEnvelopeRes = await request.get(`${baseUrl}/envelope/${createResponse.id}`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+      });
+
+      const envelope: TGetEnvelopeResponse = await getEnvelopeRes.json();
+      const envelopeItem = envelope.envelopeItems[0];
+
+      // Create field for the recipient
+      const createFieldsRequest = {
+        envelopeId: createResponse.id,
+        data: [
+          {
+            recipientId: recipient.id,
+            envelopeItemId: envelopeItem.id,
+            type: FieldType.SIGNATURE,
+            page: 1,
+            positionX: 100,
+            positionY: 100,
+            width: 50,
+            height: 50,
+          },
+        ],
+      };
+
+      const createFieldsRes = await request.post(`${baseUrl}/envelope/field/create-many`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: createFieldsRequest,
+      });
+
+      expect(createFieldsRes.ok()).toBeTruthy();
+
+      // Try to distribute the envelope - should fail
+      const distributeRes = await request.post(`${baseUrl}/envelope/distribute`, {
+        headers: { Authorization: `Bearer ${tokenA}` },
+        data: {
+          envelopeId: createResponse.id,
+        },
+      });
+
+      // Expect distribution to fail
+      expect(distributeRes.ok()).toBeFalsy();
+      expect(distributeRes.status()).toBe(400);
+
+      const errorResponse = await distributeRes.json();
+      expect(errorResponse.message).toContain('requires an email');
+    });
+  });
 });

packages/app-tests/e2e/api/v2/test-unauthorized-api-access.spec.ts

@@ -3103,7 +3103,7 @@ test.describe('Document API V2', () => {
         expect(res.status()).toBe(404);
       });
 
-      test('should allow authorized access to envelope use endpoint', async ({ page, request }) => {
+      test('should allow authorized access to envelope use endpoint', async ({ request }) => {
         const doc = await seedTemplate({
           title: 'Team template 1',
           userId: userA.id,
@@ -4313,5 +4313,62 @@ test.describe('Document API V2', () => {
         expect(res.status()).toBe(200);
       });
     });
+
+    test.describe('Envelope audit logs endpoint', () => {
+      test('should block unauthorized access to envelope audit logs endpoint', async ({
+        request,
+      }) => {
+        const doc = await seedBlankDocument(userA, teamA.id);
+
+        const res = await request.get(
+          `${WEBAPP_BASE_URL}/api/v2-beta/envelope/${doc.id}/audit-log`,
+          {
+            headers: { Authorization: `Bearer ${tokenB}` },
+          },
+        );
+
+        expect(res.ok()).toBeFalsy();
+        expect(res.status()).toBe(404);
+      });
+
+      test('should allow authorized access to envelope audit logs endpoint', async ({
+        request,
+      }) => {
+        const doc = await seedBlankDocument(userA, teamA.id);
+
+        // Add a recipient which will trigger an audit log.
+        await request.post(`${WEBAPP_BASE_URL}/api/v2-beta/envelope/recipient/create-many`, {
+          headers: { Authorization: `Bearer ${tokenA}` },
+          data: {
+            envelopeId: doc.id,
+            data: [
+              {
+                name: 'Test',
+                email: 'test@example.com',
+                role: RecipientRole.SIGNER,
+              },
+            ],
+          },
+        });
+
+        const res = await request.get(
+          `${WEBAPP_BASE_URL}/api/v2-beta/envelope/${doc.id}/audit-log`,
+          {
+            headers: { Authorization: `Bearer ${tokenA}` },
+          },
+        );
+
+        expect(res.ok()).toBeTruthy();
+        expect(res.status()).toBe(200);
+
+        const data = await res.json();
+
+        expect(Array.isArray(data.data)).toBe(true);
+        expect(data.count).toEqual(1);
+        expect(data.data[0].type).toEqual('RECIPIENT_CREATED');
+        expect(data.currentPage).toBeGreaterThanOrEqual(1);
+        expect(data.perPage).toBeGreaterThanOrEqual(1);
+      });
+    });
   });
 });

packages/app-tests/e2e/document-flow/autosave-fields-step.spec.ts

@@ -89,9 +89,8 @@ test.describe('AutoSave Fields Step', () => {
       });
 
       expect(retrievedFields.length).toBe(3);
-      expect(retrievedFields[0].type).toBe('SIGNATURE');
-      expect(retrievedFields[1].type).toBe('TEXT');
-      expect(retrievedFields[2].type).toBe('SIGNATURE');
+      expect(retrievedFields.filter((field) => field.type === 'SIGNATURE')).toHaveLength(2);
+      expect(retrievedFields.filter((field) => field.type === 'TEXT')).toHaveLength(1);
     }).toPass();
   });
 
@@ -214,10 +213,8 @@ test.describe('AutoSave Fields Step', () => {
       });
 
       expect(retrievedFields.length).toBe(4);
-      expect(retrievedFields[0].type).toBe('SIGNATURE');
-      expect(retrievedFields[1].type).toBe('TEXT');
-      expect(retrievedFields[2].type).toBe('SIGNATURE');
-      expect(retrievedFields[3].type).toBe('SIGNATURE');
+      expect(retrievedFields.filter((field) => field.type === 'SIGNATURE')).toHaveLength(3);
+      expect(retrievedFields.filter((field) => field.type === 'TEXT')).toHaveLength(1);
     }).toPass();
   });
 
@@ -259,10 +256,16 @@ test.describe('AutoSave Fields Step', () => {
       });
 
       expect(retrievedFields.length).toBe(2);
-      expect(retrievedFields[0].type).toBe('SIGNATURE');
-      expect(retrievedFields[1].type).toBe('TEXT');
+      const textField = retrievedFields.find((field) => field.type === 'TEXT');
+      const signatureField = retrievedFields.find((field) => field.type === 'SIGNATURE');
+
+      expect(signatureField).toBeDefined();
+      expect(textField).toBeDefined();
+
+      if (!signatureField || !textField) {
+        throw new Error('No signature or text field');
+      }
 
-      const textField = retrievedFields[1];
       expect(textField.fieldMeta).toBeDefined();
 
       if (

packages/app-tests/e2e/documents/delete-documents.spec.ts

@@ -9,6 +9,7 @@ import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin, apiSignout } from '../fixtures/authentication';
 import { checkDocumentTabCount } from '../fixtures/documents';
+import { expectToastTextToBeVisible, openDropdownMenu } from '../fixtures/generic';
 
 test.describe.configure({ mode: 'serial' });
 
@@ -83,14 +84,13 @@ test('[DOCUMENTS]: deleting a completed document should not remove it from recip
   });
 
   // Open document action menu.
-  await page
+  const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Completed' })
-    .getByTestId('document-table-action-btn')
-    .click();
-
-  await page.waitForTimeout(200);
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, documentActionBtn);
 
   // delete document
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click();
@@ -128,14 +128,13 @@ test('[DOCUMENTS]: deleting a pending document should remove it from recipients'
   });
 
   // Open document action menu.
-  await page
+  const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Pending' })
-    .getByTestId('document-table-action-btn')
-    .click();
-
-  await page.waitForTimeout(200);
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, documentActionBtn);
 
   // delete document
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click();
@@ -169,19 +168,17 @@ test('[DOCUMENTS]: deleting draft documents should permanently remove it', async
   });
 
   // Open document action menu.
-  await page
+  const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Draft' })
-    .getByTestId('document-table-action-btn')
-    .click();
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, documentActionBtn);
 
-  await page.waitForTimeout(200);
-
-  // delete document
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible(); // Required to reduce flakiness.
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await expect(page.getByPlaceholder("Type 'delete' to confirm")).not.toBeVisible();
   await page.getByRole('button', { name: 'Delete' }).click();
 
-  await page.waitForTimeout(2500);
+  await expectToastTextToBeVisible(page, 'Document deleted');
 
   await expect(page.getByRole('row', { name: /Document 1 - Draft/ })).not.toBeVisible();
 
@@ -203,14 +200,13 @@ test('[DOCUMENTS]: deleting pending documents should permanently remove it', asy
   });
 
   // Open document action menu.
-  await page
+  const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Pending' })
-    .getByTestId('document-table-action-btn')
-    .click();
-
-  await page.waitForTimeout(200);
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, documentActionBtn);
 
   // Delete document.
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click();
@@ -239,14 +235,13 @@ test('[DOCUMENTS]: deleting completed documents as an owner should hide it from
   });
 
   // Open document action menu.
-  await page
+  const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Completed' })
-    .getByTestId('document-table-action-btn')
-    .click();
-
-  await page.waitForTimeout(200);
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, documentActionBtn);
 
   // Delete document.
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click();
@@ -292,36 +287,24 @@ test('[DOCUMENTS]: deleting documents as a recipient should only hide it for the
   });
 
   // Open document action menu.
-  await expect(async () => {
-    await page
-      .locator('tr', { hasText: 'Document 1 - Completed' })
-      .getByTestId('document-table-action-btn')
-      .click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Hide' })).toBeVisible();
-  }).toPass();
+  const completedDocActionBtn = page
+    .locator('tr', { hasText: 'Document 1 - Completed' })
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, completedDocActionBtn);
 
   // Delete document.
-  await page.getByRole('menuitem', { name: 'Hide' }).waitFor({ state: 'visible' });
+  await expect(page.getByRole('menuitem', { name: 'Hide' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Hide' }).click({ force: true });
   await page.getByRole('button', { name: 'Hide' }).click({ force: true });
   await page.waitForTimeout(2000);
 
-  await expect(async () => {
-    await page
-      .locator('tr', { hasText: 'Document 1 - Pending' })
-      .getByTestId('document-table-action-btn')
-      .click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Hide' })).toBeVisible();
-  }).toPass();
+  const pendingDocActionBtn = page
+    .locator('tr', { hasText: 'Document 1 - Pending' })
+    .getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, pendingDocActionBtn);
 
   // Delete document.
-  await page.getByRole('menuitem', { name: 'Hide' }).waitFor({ state: 'visible' });
+  await expect(page.getByRole('menuitem', { name: 'Hide' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Hide' }).click({ force: true });
   await page.getByRole('button', { name: 'Hide' }).click({ force: true });
 

packages/app-tests/e2e/fixtures/generic.ts

@@ -1,3 +1,4 @@
+import type { Locator } from '@playwright/test';
 import { type Page, expect } from '@playwright/test';
 
 export const expectTextToBeVisible = async (page: Page, text: string) => {
@@ -7,3 +8,22 @@ export const expectTextToBeVisible = async (page: Page, text: string) => {
 export const expectTextToNotBeVisible = async (page: Page, text: string) => {
   await expect(page.getByText(text).first()).not.toBeVisible();
 };
+
+export const expectToastTextToBeVisible = async (page: Page, text: string) => {
+  await expect(page.locator('[role="status"]').getByText(text)).toBeVisible();
+};
+
+export const openDropdownMenu = async (page: Page, dropdownButton: Locator) => {
+  await page.waitForTimeout(500); // Initial timeout incase table remounts which will close the dropdown.
+  await dropdownButton.focus();
+  await page.keyboard.press('Enter');
+
+  await page.waitForTimeout(500);
+  await page.keyboard.press('Escape');
+  await page.waitForTimeout(500);
+
+  await dropdownButton.focus();
+  await page.keyboard.press('Enter');
+
+  await expect(page.getByRole('menuitem').first()).toBeVisible();
+};

packages/app-tests/e2e/folders/team-account-folders.spec.ts

@@ -9,7 +9,7 @@ import { seedTeamMember } from '@documenso/prisma/seed/teams';
 import { seedBlankTemplate } from '@documenso/prisma/seed/templates';
 
 import { apiSignin } from '../fixtures/authentication';
-import { expectTextToBeVisible } from '../fixtures/generic';
+import { expectTextToBeVisible, openDropdownMenu } from '../fixtures/generic';
 
 test.describe.configure({ mode: 'parallel' });
 
@@ -117,7 +117,9 @@ test('[TEAMS]: can pin a document folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Pin' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Pin' }).click();
 
   await page.reload();
@@ -142,7 +144,9 @@ test('[TEAMS]: can unpin a document folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Unpin' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Unpin' }).click();
 
   await page.reload();
@@ -166,7 +170,9 @@ test('[TEAMS]: can rename a document folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await page.getByLabel('Name').fill('Team Archive');
@@ -191,7 +197,9 @@ test('[TEAMS]: document folder visibility is visible to team member', async ({ p
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await expect(page.getByRole('combobox', { name: 'Visibility' })).toBeVisible();
@@ -220,7 +228,9 @@ test('[TEAMS]: document folder can be moved to another document folder', async (
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').nth(0).click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button').nth(0);
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move' }).click();
 
   await page.getByRole('button', { name: 'Team Clients' }).click();
@@ -271,7 +281,9 @@ test('[TEAMS]: document folder and its contents can be deleted', async ({ page }
     redirectPath: `/t/${team.url}/documents`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
 
   await page.getByRole('textbox').fill(`delete ${folder.name}`);
@@ -280,12 +292,8 @@ test('[TEAMS]: document folder and its contents can be deleted', async ({ page }
   await page.goto(`/t/${team.url}/documents`);
 
   await expect(page.locator(`[data-folder-id="${folder.id}"]`)).not.toBeVisible();
-  await expect(page.getByText(proposal.title)).not.toBeVisible();
-
-  await page.goto(`/t/${team.url}/documents/f/${folder.id}`);
-
-  await expect(page.getByText(report.title)).not.toBeVisible();
-  await expect(page.locator(`[data-folder-id="${reportsFolder.id}"]`)).not.toBeVisible();
+  await expect(page.getByText(proposal.title)).toBeVisible();
+  await expect(page.getByText(report.title)).toBeVisible();
 });
 
 test('[TEAMS]: create folder button is visible on templates page', async ({ page }) => {
@@ -410,7 +418,9 @@ test('[TEAMS]: can pin a template folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Pin' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Pin' }).click();
 
   await page.reload();
@@ -436,7 +446,9 @@ test('[TEAMS]: can unpin a template folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Unpin' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Unpin' }).click();
 
   await page.reload();
@@ -462,7 +474,9 @@ test('[TEAMS]: can rename a template folder', async ({ page }) => {
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await page.getByLabel('Name').fill('Updated Team Template Folder');
@@ -488,7 +502,9 @@ test('[TEAMS]: template folder visibility is not visible to team member', async
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await expect(page.getByRole('menuitem', { name: 'Visibility' })).not.toBeVisible();
@@ -519,7 +535,9 @@ test('[TEAMS]: template folder can be moved to another template folder', async (
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').nth(0).click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button').nth(0);
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move' }).click();
 
   await page.getByRole('button', { name: 'Team Client Templates' }).click();
@@ -572,7 +590,9 @@ test('[TEAMS]: template folder can be deleted', async ({ page }) => {
     redirectPath: `/t/${team.url}/templates`,
   });
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn);
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
 
   await page.getByRole('textbox').fill(`delete ${folder.name}`);
@@ -761,7 +781,9 @@ test('[TEAMS]: folder inherits team visibility settings', async ({ page }) => {
 
   await page.goto(`/t/${team.url}/documents/`);
 
-  await page.getByTestId('folder-card-more-button').click();
+  const folderMoreBtn1 = page.getByTestId('folder-card-more-button');
+  await openDropdownMenu(page, folderMoreBtn1);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await expect(page.getByRole('combobox', { name: 'Visibility' })).toHaveText('Admins only');
@@ -781,7 +803,9 @@ test('[TEAMS]: folder inherits team visibility settings', async ({ page }) => {
 
   await page.goto(`/t/${team.url}/documents`);
 
-  await page.getByTestId('folder-card-more-button').nth(0).click();
+  const folderMoreBtn2 = page.getByTestId('folder-card-more-button').nth(0);
+  await openDropdownMenu(page, folderMoreBtn2);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await expect(page.getByRole('combobox', { name: 'Visibility' })).toHaveText('Managers and above');
@@ -801,7 +825,9 @@ test('[TEAMS]: folder inherits team visibility settings', async ({ page }) => {
 
   await page.goto(`/t/${team.url}/documents/`);
 
-  await page.getByTestId('folder-card-more-button').nth(0).click();
+  const folderMoreBtn3 = page.getByTestId('folder-card-more-button').nth(0);
+  await openDropdownMenu(page, folderMoreBtn3);
+  await expect(page.getByRole('menuitem', { name: 'Settings' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Settings' }).click();
 
   await expect(page.getByRole('combobox', { name: 'Visibility' })).toHaveText('Everyone');
@@ -966,7 +992,9 @@ test('[TEAMS]: team member can move documents to everyone folder', async ({ page
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1018,7 +1046,9 @@ test('[TEAMS]: team manager can move manager document to manager folder', async
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1071,7 +1101,9 @@ test('[TEAMS]: team manager can move manager document to everyone folder', async
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1124,7 +1156,9 @@ test('[TEAMS]: team manager can move everyone document to manager folder', async
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1177,7 +1211,9 @@ test('[TEAMS]: team admin can move admin document to admin folder', async ({ pag
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1228,7 +1264,9 @@ test('[TEAMS]: team admin can move admin document to manager folder', async ({ p
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1279,7 +1317,9 @@ test('[TEAMS]: team admin can move admin document to everyone folder', async ({
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1330,7 +1370,9 @@ test('[TEAMS]: team admin can move manager document to admin folder', async ({ p
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click({ force: true });
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1381,7 +1423,9 @@ test('[TEAMS]: team admin can move manager document to manager folder', async ({
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click({ force: true });
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1432,7 +1476,9 @@ test('[TEAMS]: team admin can move manager document to everyone folder', async (
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click({ force: true });
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1483,7 +1529,9 @@ test('[TEAMS]: team admin can move everyone document to admin folder', async ({
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1534,7 +1582,9 @@ test('[TEAMS]: team admin can move everyone document to manager folder', async (
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1585,7 +1635,9 @@ test('[TEAMS]: team admin can move everyone document to everyone folder', async
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1630,7 +1682,9 @@ test('[TEAMS]: team owner can move admin document to admin folder', async ({ pag
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1675,7 +1729,9 @@ test('[TEAMS]: team owner can move admin document to manager folder', async ({ p
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1720,7 +1776,9 @@ test('[TEAMS]: team owner can move admin document to everyone folder', async ({
   await expect(page.getByText('[TEST] Admin Document')).toBeVisible();
 
   const adminDocRow = page.getByRole('row', { name: /\[TEST\] Admin Document/ });
-  await adminDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = adminDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1765,7 +1823,9 @@ test('[TEAMS]: team owner can move manager document to admin folder', async ({ p
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1810,7 +1870,9 @@ test('[TEAMS]: team owner can move manager document to manager folder', async ({
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1855,7 +1917,9 @@ test('[TEAMS]: team owner can move manager document to everyone folder', async (
   await expect(page.getByText('[TEST] Manager Document')).toBeVisible();
 
   const managerDocRow = page.getByRole('row', { name: /\[TEST\] Manager Document/ });
-  await managerDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = managerDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();
@@ -1900,7 +1964,9 @@ test('[TEAMS]: team owner can move everyone document to admin folder', async ({
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Admin Folder' })).toBeVisible();
@@ -1945,7 +2011,9 @@ test('[TEAMS]: team owner can move everyone document to manager folder', async (
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Manager Folder' })).toBeVisible();
@@ -1990,7 +2058,9 @@ test('[TEAMS]: team owner can move everyone document to everyone folder', async
   await expect(page.getByText('[TEST] Everyone Document')).toBeVisible();
 
   const everyoneDocRow = page.getByRole('row', { name: /\[TEST\] Everyone Document/ });
-  await everyoneDocRow.getByTestId('document-table-action-btn').click();
+  const docActionBtn = everyoneDocRow.getByTestId('document-table-action-btn');
+  await openDropdownMenu(page, docActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Move to Folder' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Move to Folder' }).click();
 
   await expect(page.getByRole('button', { name: 'Everyone Folder' })).toBeVisible();

packages/app-tests/e2e/organisations/manage-organisation.spec.ts

@@ -6,7 +6,11 @@ import { seedOrganisationMembers } from '@documenso/prisma/seed/organisations';
 import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin, apiSignout } from '../fixtures/authentication';
-import { expectTextToBeVisible, expectTextToNotBeVisible } from '../fixtures/generic';
+import {
+  expectTextToBeVisible,
+  expectTextToNotBeVisible,
+  openDropdownMenu,
+} from '../fixtures/generic';
 
 test('[ORGANISATIONS]: create and delete organisation', async ({ page }) => {
   const { user, organisation } = await seedUser({
@@ -399,7 +403,9 @@ test('[ORGANISATIONS]: manage groups and members', async ({ page }) => {
   await expect(page.getByText('Team members have been added').first()).toBeVisible();
 
   // Update CUSTOM_GROUP_B
-  await page.getByRole('row', { name: 'CUSTOM_GROUP_B' }).getByRole('button').click();
+  const updateBtn = page.getByRole('row', { name: 'CUSTOM_GROUP_B' }).getByRole('button');
+  await openDropdownMenu(page, updateBtn);
+  await expect(page.getByRole('menuitem', { name: 'Update role' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Update role' }).click();
   await page.getByRole('combobox').click();
   await page.getByRole('option', { name: 'Team Admin' }).click();
@@ -409,7 +415,9 @@ test('[ORGANISATIONS]: manage groups and members', async ({ page }) => {
   await page.reload();
 
   // Delete CUSTOM_GROUP_B
-  await page.getByRole('row', { name: 'CUSTOM_GROUP_B' }).getByRole('button').click();
+  const deleteBtn = page.getByRole('row', { name: 'CUSTOM_GROUP_B' }).getByRole('button');
+  await openDropdownMenu(page, deleteBtn);
+  await expect(page.getByRole('menuitem', { name: 'Remove' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Remove' }).click();
   await page.getByRole('button', { name: 'Delete' }).click();
   await expectTextToBeVisible(page, 'You have successfully removed this group from the team.');
@@ -477,7 +485,9 @@ test('[ORGANISATIONS]: member invites', async ({ page }) => {
   await expect(page.getByText(user2.email)).toBeVisible();
   await expect(page.getByText(user3.email)).toBeVisible();
 
-  await page.getByRole('row', { name: user3.email }).getByRole('button').click();
+  const inviteActionBtn = page.getByRole('row', { name: user3.email }).getByRole('button');
+  await openDropdownMenu(page, inviteActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Remove' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Remove' }).click();
   await expect(page.getByText('Invitation has been deleted').first()).toBeVisible();
   await expect(page.getByText(user3.email)).not.toBeVisible();
@@ -508,7 +518,9 @@ test('[ORGANISATIONS]: member invites', async ({ page }) => {
   await expect(page.getByText(user.email)).toBeVisible();
   await expect(page.getByText(user2.email)).toBeVisible();
 
-  await page.getByRole('row', { name: user2.email }).getByRole('button').click();
+  const memberActionBtn = page.getByRole('row', { name: user2.email }).getByRole('button');
+  await openDropdownMenu(page, memberActionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Remove' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Remove' }).click();
   await page.getByRole('button', { name: 'Remove' }).click();
   await expect(page.getByText('You have successfully removed').first()).toBeVisible();
@@ -522,7 +534,9 @@ test('[ORGANISATIONS]: member invites', async ({ page }) => {
   await expect(page.getByText(user.email)).toBeVisible();
   await expect(page.getByText(user2.email)).toBeVisible();
 
-  await page.getByRole('row', { name: user2.email }).getByRole('button').click();
+  const orgMemberBtn = page.getByRole('row', { name: user2.email }).getByRole('button');
+  await openDropdownMenu(page, orgMemberBtn);
+  await expect(page.getByRole('menuitem', { name: 'Remove' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Remove' }).click();
   await page.getByRole('button', { name: 'Delete' }).click();
   await expect(page.getByText('You have successfully removed this user').first()).toBeVisible();

packages/app-tests/e2e/public-profiles/public-profiles.spec.ts

@@ -1,10 +1,12 @@
 import { expect, test } from '@playwright/test';
 
 import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
+import { prisma } from '@documenso/prisma';
 import { seedDirectTemplate } from '@documenso/prisma/seed/templates';
 import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin } from '../fixtures/authentication';
+import { expectToastTextToBeVisible } from '../fixtures/generic';
 
 test('[PUBLIC_PROFILE]: create team profile', async ({ page }) => {
   const { user, team } = await seedUser();
@@ -44,6 +46,9 @@ test('[PUBLIC_PROFILE]: create team profile', async ({ page }) => {
     .fill('public-direct-template-description');
   await page.getByRole('button', { name: 'Update' }).click();
 
+  // Wait for toast
+  await expectToastTextToBeVisible(page, 'Template has been updated');
+
   // Check that public profile is disabled.
   await page.goto(`${NEXT_PUBLIC_WEBAPP_URL()}/p/${publicProfileUrl}`);
   await expect(page.locator('body')).toContainText('404 Profile not found');
@@ -51,7 +56,21 @@ test('[PUBLIC_PROFILE]: create team profile', async ({ page }) => {
   // Go back to public profile page.
   await page.goto(`${NEXT_PUBLIC_WEBAPP_URL()}/t/${team.url}/settings/public-profile`);
   await page.getByRole('switch').click();
-  await page.waitForTimeout(1000);
+
+  // Expect profile to be enabled via db.
+  await expect
+    .poll(
+      async () => {
+        const profile = await prisma.teamProfile.findFirst({
+          where: { teamId: team.id },
+        });
+        return profile?.enabled;
+      },
+      {
+        timeout: 1000,
+      },
+    )
+    .toBeTruthy();
 
   // Assert values.
   await page.goto(`${NEXT_PUBLIC_WEBAPP_URL()}/p/${publicProfileUrl}`);

packages/app-tests/e2e/teams/team-documents.spec.ts

@@ -11,7 +11,11 @@ import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin, apiSignout } from '../fixtures/authentication';
 import { checkDocumentTabCount } from '../fixtures/documents';
-import { expectTextToBeVisible } from '../fixtures/generic';
+import {
+  expectTextToBeVisible,
+  expectToastTextToBeVisible,
+  openDropdownMenu,
+} from '../fixtures/generic';
 
 test('[TEAMS]: check team documents count', async ({ page }) => {
   const { team, teamOwner, teamMember2 } = await seedTeamDocuments();
@@ -239,21 +243,15 @@ test('[TEAMS]: resend pending team document', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents?status=PENDING`,
   });
 
-  await expect(async () => {
-    await page.getByTestId('document-table-action-btn').first().click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Resend' })).toBeVisible();
-  }).toPass();
-
-  await page.getByRole('menuitem').filter({ hasText: 'Resend' }).click();
+  const actionBtn = page.getByTestId('document-table-action-btn').first();
+  await expect(actionBtn).toBeAttached();
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Resend' })).toBeVisible();
+  await page.getByRole('menuitem', { name: 'Resend' }).click();
   await page.getByLabel('test.documenso.com').first().click();
   await page.getByRole('button', { name: 'Send reminder' }).click();
 
-  await expect(
-    page.getByRole('status').filter({ hasText: 'Document re-sent' }).first(),
-  ).toBeVisible();
+  await expectToastTextToBeVisible(page, 'Document re-sent');
 });
 
 test('[TEAMS]: delete draft team document', async ({ page }) => {
@@ -265,14 +263,12 @@ test('[TEAMS]: delete draft team document', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents?status=DRAFT`,
   });
 
-  await expect(async () => {
-    await page.getByTestId('document-table-action-btn').first().click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
-  }).toPass();
-
+  const actionBtn = page.getByTestId('document-table-action-btn').first();
+  await expect(actionBtn).toBeVisible({
+    timeout: 500,
+  });
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
   await page.getByRole('button', { name: 'Delete' }).click();
 
@@ -309,14 +305,12 @@ test('[TEAMS]: delete pending team document', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents?status=PENDING`,
   });
 
-  await expect(async () => {
-    await page.getByTestId('document-table-action-btn').first().click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
-  }).toPass();
-
+  const actionBtn = page.getByTestId('document-table-action-btn').first();
+  await expect(actionBtn).toBeVisible({
+    timeout: 500,
+  });
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click({ force: true });
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click({ force: true });
@@ -354,14 +348,12 @@ test('[TEAMS]: delete completed team document', async ({ page }) => {
     redirectPath: `/t/${team.url}/documents?status=COMPLETED`,
   });
 
-  await expect(async () => {
-    await page.getByTestId('document-table-action-btn').first().click();
-
-    await page.waitForTimeout(1000);
-
-    await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
-  }).toPass();
-
+  const actionBtn = page.getByTestId('document-table-action-btn').first();
+  await expect(actionBtn).toBeVisible({
+    timeout: 500,
+  });
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click({ force: true });
   await page.getByPlaceholder("Type 'delete' to confirm").fill('delete');
   await page.getByRole('button', { name: 'Delete' }).click({ force: true });

packages/app-tests/e2e/teams/team-email.spec.ts

@@ -5,6 +5,7 @@ import { seedTeamEmailVerification } from '@documenso/prisma/seed/teams';
 import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin } from '../fixtures/authentication';
+import { openDropdownMenu } from '../fixtures/generic';
 
 test('[TEAMS]: send team email request', async ({ page }) => {
   const { user, team } = await seedUser();
@@ -54,8 +55,13 @@ test('[TEAMS]: delete team email', async ({ page }) => {
     redirectPath: `/t/${team.url}/settings`,
   });
 
-  await page.locator('section div').filter({ hasText: 'Team email' }).getByRole('button').click();
+  const settingsBtn = page
+    .locator('section div')
+    .filter({ hasText: 'Team email' })
+    .getByRole('button');
+  await openDropdownMenu(page, settingsBtn);
 
+  await expect(page.getByRole('menuitem', { name: 'Remove' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Remove' }).click();
   await page.getByRole('button', { name: 'Remove' }).click();
 

packages/app-tests/e2e/templates-flow/template-autosave-fields-step.spec.ts

@@ -296,7 +296,13 @@ test.describe('AutoSave Fields Step', () => {
         ['SIGNATURE', 'TEXT'].toSorted(),
       );
 
-      const textField = fields[1];
+      const textField = fields.find((field) => field.type === 'TEXT');
+      expect(textField).toBeDefined();
+
+      if (!textField) {
+        throw new Error('No text field');
+      }
+
       expect(textField.fieldMeta).toBeDefined();
 
       if (

packages/app-tests/e2e/templates/manage-templates.spec.ts

@@ -5,6 +5,7 @@ import { seedTeam, seedTeamMember } from '@documenso/prisma/seed/teams';
 import { seedTemplate } from '@documenso/prisma/seed/templates';
 
 import { apiSignin } from '../fixtures/authentication';
+import { openDropdownMenu } from '../fixtures/generic';
 
 test('[TEMPLATES]: view templates', async ({ page }) => {
   const { team, owner, organisation } = await seedTeam({
@@ -71,13 +72,14 @@ test('[TEMPLATES]: delete template', async ({ page }) => {
   });
 
   for (const template of ['Team template 1', 'Team template 2']) {
-    await page
+    const actionBtn = page
       .getByRole('row', { name: template })
       .getByRole('cell', { name: 'Use Template' })
       .getByRole('button')
-      .nth(1)
-      .click();
+      .nth(1);
+    await openDropdownMenu(page, actionBtn);
 
+    await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
     await page.getByRole('menuitem', { name: 'Delete' }).click();
     await page.getByRole('button', { name: 'Delete' }).click();
     await expect(page.getByText('Template deleted').first()).toBeVisible();
@@ -110,7 +112,9 @@ test('[TEMPLATES]: duplicate template', async ({ page }) => {
   });
 
   // Duplicate team template.
-  await page.getByRole('cell', { name: 'Use Template' }).getByRole('button').nth(1).click();
+  const actionBtn = page.getByRole('cell', { name: 'Use Template' }).getByRole('button').nth(1);
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Duplicate' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Duplicate' }).click();
   await page.getByRole('button', { name: 'Duplicate' }).click();
   await expect(page.getByText('Template duplicated').first()).toBeVisible();

packages/app-tests/e2e/webhooks/webhooks-crud.spec.ts

@@ -7,7 +7,7 @@ import { seedBlankDocument } from '@documenso/prisma/seed/documents';
 import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin, apiSignout } from '../fixtures/authentication';
-import { expectTextToBeVisible } from '../fixtures/generic';
+import { expectTextToBeVisible, openDropdownMenu } from '../fixtures/generic';
 
 /**
  * Helper function to seed a webhook directly in the database for testing.
@@ -147,9 +147,11 @@ test('[WEBHOOKS]: delete webhook', async ({ page }) => {
 
   // Find the row with the webhook and click the action dropdown
   const webhookRow = page.locator('tr', { hasText: webhookUrl });
-  await webhookRow.getByTestId('webhook-table-action-btn').click();
+  const actionBtn = webhookRow.getByTestId('webhook-table-action-btn');
+  await openDropdownMenu(page, actionBtn);
 
   // Click Delete menu item
+  await expect(page.getByRole('menuitem', { name: 'Delete' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Delete' }).click();
 
   // Fill in confirmation field
@@ -196,9 +198,11 @@ test('[WEBHOOKS]: update webhook', async ({ page }) => {
 
   // Find the row with the webhook and click the action dropdown
   const webhookRow = page.locator('tr', { hasText: originalWebhookUrl });
-  await webhookRow.getByTestId('webhook-table-action-btn').click();
+  const actionBtn = webhookRow.getByTestId('webhook-table-action-btn');
+  await openDropdownMenu(page, actionBtn);
 
   // Click Edit menu item
+  await expect(page.getByRole('menuitem', { name: 'Edit' })).toBeVisible();
   await page.getByRole('menuitem', { name: 'Edit' }).click();
 
   // Wait for dialog to open

packages/app-tests/package.json

@@ -7,14 +7,14 @@
   "scripts": {
     "test:dev": "NODE_OPTIONS=--experimental-require-module playwright test",
     "test-ui:dev": "NODE_OPTIONS=--experimental-require-module playwright test --ui",
-    "test:e2e": "NODE_OPTIONS=--experimental-require-module NODE_ENV=test start-server-and-test \"npm run start -w @documenso/remix\" http://localhost:3000 \"playwright test $E2E_TEST_PATH\""
+    "test:e2e": "NODE_OPTIONS=--experimental-require-module NODE_ENV=test NEXT_PRIVATE_LOGGER_FILE_PATH=./logs.json start-server-and-test \"npm run start -w @documenso/remix\" http://localhost:3000 \"playwright test $E2E_TEST_PATH\""
   },
   "keywords": [],
   "author": "",
   "devDependencies": {
     "@documenso/lib": "*",
     "@documenso/prisma": "*",
-    "@napi-rs/canvas": "^0.1.82",
+    "@napi-rs/canvas": "^0.1.83",
     "@playwright/test": "1.56.1",
     "@types/node": "^20",
     "@types/pngjs": "^6.0.5",

packages/app-tests/playwright.config.ts

@@ -1,7 +1,21 @@
 import { defineConfig, devices } from '@playwright/test';
 import dotenv from 'dotenv';
+import os from 'os';
 import path from 'path';
 
+function calculateWorkers() {
+  const total = os.cpus().length;
+
+  // Reserve 2 cores for the system
+  const usable = Math.max(total - 2, 1);
+
+  // 1 worker per 2 cores, minimum 1
+  const workers = Math.max(Math.floor(usable / 2), 1);
+
+  // Max 6 workers
+  return Math.min(workers, 6);
+}
+
 const ENV_FILES = ['.env', '.env.local', `.env.${process.env.NODE_ENV || 'development'}`];
 
 ENV_FILES.forEach((file) => {
@@ -15,9 +29,8 @@ ENV_FILES.forEach((file) => {
  */
 export default defineConfig({
   testDir: './e2e',
-  /* Run tests in files in parallel */
-  fullyParallel: false,
-  workers: 2,
+  fullyParallel: true,
+  workers: 10, // See Projects where 10 is utilized for API tests. We're not running 10 workers for UI tests.
   maxFailures: process.env.CI ? 1 : undefined,
   /* Fail the build on CI if you accidentally left test.only in the source code. */
   forbidOnly: !!process.env.CI,
@@ -31,25 +44,54 @@ export default defineConfig({
     baseURL: 'http://localhost:3000',
 
     /* Collect trace when retrying the failed test. See https://playwright.dev/docs/trace-viewer */
-    trace: 'on',
-
-    video: 'on-first-retry',
+    trace: 'retain-on-failure',
+    video: 'retain-on-failure',
 
     /* Add explicit timeouts for actions */
     actionTimeout: 15_000,
     navigationTimeout: 30_000,
+
+    contextOptions: {
+      reducedMotion: 'reduce',
+    },
+
+    /* Disable animations via cookie for more stable tests */
+    storageState: {
+      cookies: [
+        {
+          name: '__disable_animations',
+          value: 'true',
+          domain: 'localhost',
+          path: '/',
+          expires: -1,
+          httpOnly: false,
+          secure: false,
+          sameSite: 'Lax' as const,
+        },
+      ],
+      origins: [],
+    },
   },
 
   timeout: 60_000,
 
   /* Configure projects for major browsers */
   projects: [
+    // API Tests e2e/api/**/*.spec.ts
     {
-      name: 'chromium',
+      name: 'api',
+      testMatch: /e2e\/api\/.*\.spec\.ts/,
+      workers: 10, // Limited by DB connections before it gets flakey.
+    },
+    // Run UI Tests
+    {
+      name: 'ui',
+      testMatch: /e2e\/(?!api\/).*\.spec\.ts/,
       use: {
         ...devices['Desktop Chrome'],
         viewport: { width: 1920, height: 1200 },
       },
+      workers: calculateWorkers(),
     },
 
     // {

packages/email/package.json

@@ -32,17 +32,17 @@
     "@react-email/img": "0.0.11",
     "@react-email/link": "0.0.12",
     "@react-email/preview": "0.0.13",
-    "@react-email/render": "0.0.17",
+    "@react-email/render": "2.0.0",
     "@react-email/row": "0.0.12",
     "@react-email/section": "0.0.16",
     "@react-email/tailwind": "^2.0.1",
     "@react-email/text": "0.1.5",
     "nodemailer": "^7.0.10",
-    "react-email": "^5.0.4",
+    "react-email": "^5.0.6",
     "resend": "^6.5.2"
   },
   "devDependencies": {
     "@documenso/tsconfig": "*",
-    "@types/nodemailer": "^6.4.21"
+    "@types/nodemailer": "^7.0.4"
   }
-}
+}

packages/email/render.tsx

@@ -15,7 +15,7 @@ export type RenderOptions = ReactEmail.Options & {
 // eslint-disable-next-line @typescript-eslint/consistent-type-assertions
 const colors = (config.theme?.extend?.colors || {}) as Record<string, string>;
 
-export const render = (element: React.ReactNode, options?: RenderOptions) => {
+export const render = async (element: React.ReactNode, options?: RenderOptions) => {
   const { branding, ...otherOptions } = options ?? {};
 
   return ReactEmail.render(
@@ -36,7 +36,7 @@ export const render = (element: React.ReactNode, options?: RenderOptions) => {
   );
 };
 
-export const renderWithI18N = (element: React.ReactNode, options?: RenderOptions) => {
+export const renderWithI18N = async (element: React.ReactNode, options?: RenderOptions) => {
   const { branding, i18n, ...otherOptions } = options ?? {};
 
   if (!i18n) {
@@ -62,24 +62,3 @@ export const renderWithI18N = (element: React.ReactNode, options?: RenderOptions
     otherOptions,
   );
 };
-
-export const renderAsync = async (element: React.ReactNode, options?: RenderOptions) => {
-  const { branding, ...otherOptions } = options ?? {};
-
-  return await ReactEmail.renderAsync(
-    <BrandingProvider branding={branding}>
-      <Tailwind
-        config={{
-          theme: {
-            extend: {
-              colors,
-            },
-          },
-        }}
-      >
-        {element}
-      </Tailwind>
-    </BrandingProvider>,
-    otherOptions,
-  );
-};

packages/lib/client-only/providers/envelope-editor-provider.tsx

@@ -132,7 +132,12 @@ export const EnvelopeEditorProvider = ({
   });
 
   const envelopeFieldSetMutationQuery = trpc.envelope.field.set.useMutation({
-    onSuccess: () => {
+    onSuccess: ({ data: fields }) => {
+      setEnvelope((prev) => ({
+        ...prev,
+        fields,
+      }));
+
       setAutosaveError(false);
     },
     onError: (err) => {
@@ -154,8 +159,18 @@ export const EnvelopeEditorProvider = ({
       setEnvelope((prev) => ({
         ...prev,
         recipients,
+        fields: prev.fields.filter((field) =>
+          recipients.some((recipient) => recipient.id === field.recipientId),
+        ),
       }));
 
+      // Reset the local fields to ensure deleted recipient fields are removed.
+      editorFields.resetForm(
+        envelope.fields.filter((field) =>
+          recipients.some((recipient) => recipient.id === field.recipientId),
+        ),
+      );
+
       setAutosaveError(false);
     },
     onError: (err) => {
@@ -265,7 +280,7 @@ export const EnvelopeEditorProvider = ({
   );
 
   /**
-   * Fetch and sycn the envelope back into the editor.
+   * Fetch and sync the envelope back into the editor.
    *
    * Overrides everything.
    */

packages/lib/constants/app.ts

@@ -18,3 +18,6 @@ export const SUPPORT_EMAIL = env('NEXT_PUBLIC_SUPPORT_EMAIL') ?? 'support@docume
 
 export const USE_INTERNAL_URL_BROWSERLESS = () =>
   env('NEXT_PUBLIC_USE_INTERNAL_URL_BROWSERLESS') === 'true';
+
+export const IS_AI_FEATURES_CONFIGURED = () =>
+  !!env('GOOGLE_VERTEX_PROJECT_ID') && !!env('GOOGLE_VERTEX_API_KEY');

packages/lib/constants/i18n.ts

@@ -6,6 +6,7 @@ export const SUPPORTED_LANGUAGE_CODES = [
   'fr',
   'es',
   'it',
+  'nl',
   'pl',
   'pt-BR',
   'ja',
@@ -61,6 +62,10 @@ export const SUPPORTED_LANGUAGES: Record<string, SupportedLanguage> = {
     full: 'Italian',
     short: 'it',
   },
+  nl: {
+    short: 'nl',
+    full: 'Dutch',
+  },
   pl: {
     short: 'pl',
     full: 'Polish',

packages/lib/jobs/definitions/emails/send-document-cancelled-emails.handler.ts

@@ -5,6 +5,7 @@ import { EnvelopeType, ReadStatus, SendStatus, SigningStatus } from '@prisma/cli
 
 import { mailer } from '@documenso/email/mailer';
 import DocumentCancelTemplate from '@documenso/email/templates/document-cancel';
+import { isRecipientEmailValidForSending } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 
 import { getI18nInstance } from '../../../client-only/providers/i18n-server';
@@ -77,7 +78,8 @@ export const run = async ({
   const recipientsToNotify = envelope.recipients.filter(
     (recipient) =>
       (recipient.sendStatus === SendStatus.SENT || recipient.readStatus === ReadStatus.OPENED) &&
-      recipient.signingStatus !== SigningStatus.REJECTED,
+      recipient.signingStatus !== SigningStatus.REJECTED &&
+      isRecipientEmailValidForSending(recipient),
   );
 
   await io.runTask('send-cancellation-emails', async () => {

packages/lib/jobs/definitions/emails/send-recipient-signed-email.handler.ts

@@ -12,6 +12,7 @@ import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
 import { getEmailContext } from '../../../server-only/email/get-email-context';
 import { extractDerivedDocumentEmailSettings } from '../../../types/document-email';
 import { unsafeBuildEnvelopeIdQuery } from '../../../utils/envelope';
+import { isRecipientEmailValidForSending } from '../../../utils/recipients';
 import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
 import type { JobRunIO } from '../../client/_internal/job';
 import type { TSendRecipientSignedEmailJobDefinition } from './send-recipient-signed-email';
@@ -79,8 +80,8 @@ export const run = async ({
 
   const recipientReference = recipientName || recipientEmail;
 
-  // Don't send notification if the owner is the one who signed
-  if (owner.email === recipientEmail) {
+  // Don't send notification if the owner is the one who signed.
+  if (owner.email === recipientEmail || !isRecipientEmailValidForSending(recipient)) {
     return;
   }
 

packages/lib/jobs/definitions/emails/send-rejection-emails.handler.ts

@@ -6,6 +6,7 @@ import { EnvelopeType, SendStatus, SigningStatus } from '@prisma/client';
 import { mailer } from '@documenso/email/mailer';
 import DocumentRejectedEmail from '@documenso/email/templates/document-rejected';
 import DocumentRejectionConfirmedEmail from '@documenso/email/templates/document-rejection-confirmed';
+import { isRecipientEmailValidForSending } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 
 import { getI18nInstance } from '../../../client-only/providers/i18n-server';
@@ -85,36 +86,38 @@ export const run = async ({
   const i18n = await getI18nInstance(emailLanguage);
 
   // Send confirmation email to the recipient who rejected
-  await io.runTask('send-rejection-confirmation-email', async () => {
-    const recipientTemplate = createElement(DocumentRejectionConfirmedEmail, {
-      recipientName: recipient.name,
-      documentName: envelope.title,
-      documentOwnerName: envelope.user.name || envelope.user.email,
-      reason: recipient.rejectionReason || '',
-      assetBaseUrl: NEXT_PUBLIC_WEBAPP_URL(),
-    });
+  if (isRecipientEmailValidForSending(recipient)) {
+    await io.runTask('send-rejection-confirmation-email', async () => {
+      const recipientTemplate = createElement(DocumentRejectionConfirmedEmail, {
+        recipientName: recipient.name,
+        documentName: envelope.title,
+        documentOwnerName: envelope.user.name || envelope.user.email,
+        reason: recipient.rejectionReason || '',
+        assetBaseUrl: NEXT_PUBLIC_WEBAPP_URL(),
+      });
 
-    const [html, text] = await Promise.all([
-      renderEmailWithI18N(recipientTemplate, { lang: emailLanguage, branding }),
-      renderEmailWithI18N(recipientTemplate, {
-        lang: emailLanguage,
-        branding,
-        plainText: true,
-      }),
-    ]);
+      const [html, text] = await Promise.all([
+        renderEmailWithI18N(recipientTemplate, { lang: emailLanguage, branding }),
+        renderEmailWithI18N(recipientTemplate, {
+          lang: emailLanguage,
+          branding,
+          plainText: true,
+        }),
+      ]);
 
-    await mailer.sendMail({
-      to: {
-        name: recipient.name,
-        address: recipient.email,
-      },
-      from: senderEmail,
-      replyTo: replyToEmail,
-      subject: i18n._(msg`Document "${envelope.title}" - Rejection Confirmed`),
-      html,
-      text,
+      await mailer.sendMail({
+        to: {
+          name: recipient.name,
+          address: recipient.email,
+        },
+        from: senderEmail,
+        replyTo: replyToEmail,
+        subject: i18n._(msg`Document "${envelope.title}" - Rejection Confirmed`),
+        html,
+        text,
+      });
     });
-  });
+  }
 
   // Send notification email to document owner
   await io.runTask('send-owner-notification-email', async () => {

packages/lib/jobs/definitions/emails/send-signing-email.handler.ts

@@ -12,6 +12,7 @@ import {
 
 import { mailer } from '@documenso/email/mailer';
 import DocumentInviteEmailTemplate from '@documenso/email/templates/document-invite';
+import { isRecipientEmailValidForSending } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 
 import { getI18nInstance } from '../../../client-only/providers/i18n-server';
@@ -177,31 +178,33 @@ export const run = async ({
     includeSenderDetails: settings.includeSenderDetails,
   });
 
-  await io.runTask('send-signing-email', async () => {
-    const [html, text] = await Promise.all([
-      renderEmailWithI18N(template, { lang: emailLanguage, branding }),
-      renderEmailWithI18N(template, {
-        lang: emailLanguage,
-        branding,
-        plainText: true,
-      }),
-    ]);
+  if (isRecipientEmailValidForSending(recipient)) {
+    await io.runTask('send-signing-email', async () => {
+      const [html, text] = await Promise.all([
+        renderEmailWithI18N(template, { lang: emailLanguage, branding }),
+        renderEmailWithI18N(template, {
+          lang: emailLanguage,
+          branding,
+          plainText: true,
+        }),
+      ]);
 
-    await mailer.sendMail({
-      to: {
-        name: recipient.name,
-        address: recipient.email,
-      },
-      from: senderEmail,
-      replyTo: replyToEmail,
-      subject: renderCustomEmailTemplate(
-        documentMeta?.subject || emailSubject,
-        customEmailTemplate,
-      ),
-      html,
-      text,
+      await mailer.sendMail({
+        to: {
+          name: recipient.name,
+          address: recipient.email,
+        },
+        from: senderEmail,
+        replyTo: replyToEmail,
+        subject: renderCustomEmailTemplate(
+          documentMeta?.subject || emailSubject,
+          customEmailTemplate,
+        ),
+        html,
+        text,
+      });
     });
-  });
+  }
 
   await io.runTask('update-recipient', async () => {
     await prisma.recipient.update({

packages/lib/package.json

@@ -15,6 +15,7 @@
     "clean": "rimraf node_modules"
   },
   "dependencies": {
+    "@ai-sdk/google-vertex": "3.0.81",
     "@aws-sdk/client-s3": "^3.936.0",
     "@aws-sdk/client-sesv2": "^3.936.0",
     "@aws-sdk/cloudfront-signer": "^3.935.0",
@@ -27,6 +28,7 @@
     "@lingui/core": "^5.6.0",
     "@lingui/macro": "^5.6.0",
     "@lingui/react": "^5.6.0",
+    "@napi-rs/canvas": "^0.1.83",
     "@noble/ciphers": "0.6.0",
     "@noble/hashes": "1.8.0",
     "@node-rs/bcrypt": "^1.10.7",
@@ -35,6 +37,7 @@
     "@sindresorhus/slugify": "^3.0.0",
     "@team-plain/typescript-sdk": "^5.11.0",
     "@vvo/tzdb": "^6.196.0",
+    "ai": "^5.0.104",
     "csv-parse": "^6.1.0",
     "inngest": "^3.45.1",
     "jose": "^6.1.2",
@@ -43,6 +46,7 @@
     "luxon": "^3.7.2",
     "nanoid": "^5.1.6",
     "oslo": "^0.17.0",
+    "p-map": "^7.0.4",
     "pg": "^8.16.3",
     "pino": "^9.14.0",
     "pino-pretty": "^13.1.2",
@@ -63,4 +67,4 @@
     "@types/luxon": "^3.7.1",
     "@types/pg": "^8.15.6"
   }
-}
+}