Merge branch 'main' into feature/pdf-placeholder-selection-fields

Adds a dedicated self-hosting page documenting how to apply an
Enterprise license key, and cross-links it from the related docs.

New page: self-hosting/configuration/license.mdx — "Apply Your License
Key"
Set NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY (Docker Compose / docker run /
.env tabs)

.agents/plans/brisk-cobalt-river-pdf-placeholder-selection-fields.md

@@ -0,0 +1,222 @@
+---
+date: 2026-05-07
+title: Pdf Placeholder Selection Fields
+---
+
+## Summary
+
+Extend PDF placeholders so radio and dropdown fields can be configured from the existing Documenso placeholder syntax:
+
+```text
+{{FIELD_TYPE, RECIPIENT, key=value, key=value}}
+```
+
+Do not introduce a new delimiter style. Existing applications may already generate placeholders in this format, so the new selection-field behavior should fit into it.
+
+## Goals
+
+- Keep the current placeholder grammar unchanged.
+- Support checkbox placeholders with option lists, checked values, validation, direction, required, read-only, and font size.
+- Support radio placeholders with option lists, default/preselected values, direction, required, read-only, and font size.
+- Support dropdown placeholders with option lists, default value, required, read-only, and font size.
+- Use `options` as the only public list key in PDF placeholders.
+- Convert `options` into internal `fieldMeta.values` during parsing.
+- Make generated fields usable immediately in the editor, signing UI, preview renderer, and final PDF export.
+
+## Non-Goals
+
+- No semicolon placeholder syntax.
+- No `values` alias in PDF placeholder syntax.
+- No database migration.
+- No behavior change for existing placeholders such as `{{text, r1, required=true}}`.
+
+## Placeholder Syntax
+
+Use the existing comma-separated placeholder format:
+
+```text
+{{checkbox, r1, options=Email|SMS|Phone, checked=Email|Phone, validationRule=atLeast, validationLength=1}}
+{{radio, r1, options=Card|Bank transfer|Check, defaultValue=Check}}
+{{radio, r1, options=Basic|Pro|Enterprise, selected=Pro, direction=horizontal}}
+{{dropdown, r1, options=United States|Canada|United Kingdom}}
+{{dropdown, r2, options=Sales|Legal|Finance, defaultValue=Legal}}
+```
+
+Use `|` inside `options` because `,` is already the top-level placeholder delimiter.
+
+Parsing rules:
+
+- Split top-level placeholder tokens on unescaped commas.
+- Split metadata tokens on the first unescaped equals sign.
+- Split `options` on unescaped pipes.
+- Trim option values and drop empty values.
+- Preserve option order.
+- Support escaped delimiters: `\,`, `\=`, and `\|`.
+- Treat field type values case-insensitively.
+
+## Field Type Mapping
+
+- `checkbox` maps to `FieldType.CHECKBOX`.
+- `radio` maps to `FieldType.RADIO`.
+- `dropdown` maps to `FieldType.DROPDOWN`.
+
+## Metadata Mapping
+
+### Checkbox
+
+Example:
+
+```text
+{{checkbox, r1, options=Email|SMS|Phone, checked=Email|Phone, validationRule=atLeast, validationLength=1}}
+```
+
+Normalize to:
+
+```ts
+{
+  type: FieldType.CHECKBOX,
+  fieldMeta: {
+    type: 'checkbox',
+    validationRule: 'Select at least',
+    validationLength: 1,
+    values: [
+      { id: 1, value: 'Email', checked: true },
+      { id: 2, value: 'SMS', checked: false },
+      { id: 3, value: 'Phone', checked: true },
+    ],
+  },
+}
+```
+
+Accepted keys:
+
+- `options`
+- `checked`
+- `direction=vertical|horizontal`
+- `validationRule=atLeast|exactly|atMost`
+- `validationLength=1`
+- `required=true|false`
+- `readOnly=true|false`
+- `fontSize=12`
+
+Map checkbox validation aliases internally: `atLeast` -> `Select at least`, `exactly` -> `Select exactly`, `atMost` -> `Select at most`.
+
+Checkbox placeholders do not support `label` or `placeholder` metadata.
+
+### Radio
+
+Example:
+
+```text
+{{radio, r1, options=Card|Bank transfer|Check, selected=Bank transfer}}
+```
+
+Normalize to:
+
+```ts
+{
+  type: FieldType.RADIO,
+  fieldMeta: {
+    type: 'radio',
+    values: [
+      { id: 1, value: 'Card', checked: false },
+      { id: 2, value: 'Bank transfer', checked: true },
+      { id: 3, value: 'Check', checked: false },
+    ],
+  },
+}
+```
+
+Accepted keys:
+
+- `options`
+- `selected`, `default`, or `defaultValue`
+- `direction=vertical|horizontal`
+- `required=true|false`
+- `readOnly=true|false`
+- `fontSize=12`
+
+Radio placeholders do not support `label` or `placeholder` metadata.
+
+### Dropdown
+
+Example:
+
+```text
+{{dropdown, r1, options=Sales|Legal|Finance, defaultValue=Legal}}
+```
+
+Normalize to:
+
+```ts
+{
+  type: FieldType.DROPDOWN,
+  fieldMeta: {
+    type: 'dropdown',
+    values: [{ value: 'Sales' }, { value: 'Legal' }, { value: 'Finance' }],
+    defaultValue: 'Legal',
+  },
+}
+```
+
+Accepted keys:
+
+- `options`
+- `selected`, `default`, or `defaultValue`
+- `required=true|false`
+- `readOnly=true|false`
+- `fontSize=12`
+
+`defaultValue` should only be set if it matches one parsed option.
+
+Dropdown placeholders do not support `label` or `placeholder` metadata.
+
+## Code Touchpoints
+
+- `packages/lib/server-only/pdf/helpers.ts`
+  - Extend `parseFieldMetaFromPlaceholder` so `options` normalizes into checkbox/radio/dropdown `fieldMeta.values`.
+  - Add delimiter-aware helpers for commas, equals signs, and pipes.
+- `packages/lib/server-only/pdf/auto-place-fields.ts`
+  - Replace plain comma splitting with delimiter-aware splitting.
+  - Preserve the existing positional structure: field type, recipient, metadata.
+- `packages/lib/types/field-meta.ts`
+  - Keep current internal schemas: checkbox/radio/dropdown still store options as `fieldMeta.values`.
+- `packages/ui/primitives/document-flow/field-content.tsx`
+  - Display a radio fallback when a placeholder-created radio has no options.
+- Docs:
+  - `apps/docs/content/docs/users/documents/advanced/pdf-placeholders.mdx`
+  - `apps/docs/content/docs/developers/api/fields.mdx`
+
+## Test Plan
+
+Unit tests:
+
+- `options=Yes|No|Maybe` becomes stable radio values.
+- `selected=No` marks only the matching radio option checked.
+- Checkbox `options`, `checked`, `validationRule`, and `validationLength` normalize correctly.
+- Dropdown `options` and `defaultValue` normalize correctly.
+- Escaped delimiters parse correctly, for example `options=Sales\|Ops|Legal\, Compliance|A\=B`.
+
+E2E/API tests:
+
+- Add a PDF fixture with checkbox, radio, and dropdown placeholders using the current syntax.
+- Verify created fields have schema-compatible metadata and expected options/defaults.
+
+Suggested verification:
+
+```bash
+npm run test -w @documenso/lib -- server-only/pdf/helpers.test.ts
+npm run test:dev -w @documenso/app-tests -- e2e/auto-placing-fields/auto-place-fields-document.spec.ts
+npm run test:dev -w @documenso/app-tests -- e2e/envelope-editor-v2/envelope-fields.spec.ts
+npx tsc --noEmit -p packages/lib/tsconfig.json
+npx tsc --noEmit -p apps/remix/tsconfig.json
+```
+
+Do not use `npm run build` for routine verification unless explicitly requested.
+
+## Decisions
+
+- Keep the existing placeholder format.
+- Use only `options` publicly.
+- Keep `values` as an internal metadata field only.
+- Use `|` as the option delimiter inside `options`.

apps/docs/content/docs/policies/enterprise-edition.mdx

@@ -76,6 +76,8 @@ The Enterprise Edition is required when you:
     4. Restart your Documenso instance
     5. Verify the license is active in the **Admin Panel** under the **Stats** section
 
+    See [Apply Your License Key](/docs/self-hosting/configuration/license) for the full walkthrough, including how to enable individual features once licensed.
+
   </Accordion>
 </Accordions>
 
@@ -197,7 +199,7 @@ See [Support](/docs/policies/support) for complete support options.
     1. Sign the Enterprise license agreement
     2. Receive license key and access credentials
     3. Deploy using [self-hosting guides](/docs/self-hosting) or access Documenso Cloud
-    4. Configure Enterprise features with support assistance
+    4. Apply the key — see [Apply Your License Key](/docs/self-hosting/configuration/license) — and configure Enterprise features with support assistance
 
   </Step>
   <Step>
@@ -238,6 +240,7 @@ See [Support](/docs/policies/support) for complete support options.
 
 ## Related
 
+- [Apply Your License Key](/docs/self-hosting/configuration/license) - Step-by-step license activation
 - [Community Edition](/docs/policies/community-edition) - AGPL-3.0 open-source license
 - [Licenses](/docs/policies/licenses) - Complete licensing overview and FAQ
 - [Support](/docs/policies/support) - Support channels and response times

apps/docs/content/docs/self-hosting/configuration/environment.mdx

@@ -443,11 +443,11 @@ Telemetry collects only: app version, installation ID, and node ID. No personal
 
 ## Enterprise Features
 
-These variables require an active [Enterprise Edition](/docs/policies/enterprise-edition) license. Obtain a license key from [license.documenso.com](https://license.documenso.com) and set it below to unlock enterprise features such as SSO, embed editor, and 21 CFR Part 11 compliance.
+These variables require an active [Enterprise Edition](/docs/policies/enterprise-edition) license. Obtain a license key from [license.documenso.com](https://license.documenso.com) and set it below to unlock enterprise features such as SSO, embed editor, and 21 CFR Part 11 compliance. See [Apply Your License Key](/docs/self-hosting/configuration/license) for step-by-step setup.
 
 | Variable                             | Description                                      |
 | ------------------------------------ | ------------------------------------------------ |
-| `NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY` | License key for enterprise features              |
+| `NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY` | License key for enterprise features — see [Apply Your License Key](/docs/self-hosting/configuration/license) for how to apply it |
 | `NEXT_PRIVATE_STRIPE_API_KEY`        | Stripe API key for billing                       |
 | `NEXT_PRIVATE_STRIPE_WEBHOOK_SECRET` | Stripe webhook secret                            |
 | `NEXT_PRIVATE_SES_ACCESS_KEY_ID`     | AWS SES access key for email domain verification |

apps/docs/content/docs/self-hosting/configuration/license.mdx

@@ -0,0 +1,107 @@
+---
+title: Apply Your License Key
+description: Activate your Enterprise license key to unlock enterprise features on your self-hosted instance.
+---
+
+import { Accordion, Accordions } from 'fumadocs-ui/components/accordion';
+import { Callout } from 'fumadocs-ui/components/callout';
+import { Tab, Tabs } from 'fumadocs-ui/components/tabs';
+
+A license key activates the Enterprise features available to your self-hosted instance, such as CSC signing, SSO, embed white-labelling, and 21 CFR Part 11 compliance.
+
+<Callout type="info">
+  The license key applies to your **whole instance**, not an individual user account. There's one
+  key per deployment.
+</Callout>
+
+## Prerequisites
+
+- An active Enterprise license key — contact [sales](https://documen.so/enterprise) to set up an
+  Enterprise subscription, then copy your key from [license.documenso.com](https://license.documenso.com).
+  See [Enterprise Edition](/docs/policies/enterprise-edition) for details.
+- A running self-hosted Documenso instance that you're able to restart
+
+## Step 1: Set the environment variable
+
+Set `NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY` to your license key.
+
+<Tabs items={['Docker Compose', 'docker run', '.env']}>
+<Tab value="Docker Compose">
+
+Add the variable to your `.env` file (or directly under `environment:` in `compose.yml`):
+
+```bash
+NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY=your-license-key-here
+```
+
+Then apply it:
+
+```bash
+docker compose up -d
+```
+
+</Tab>
+<Tab value="docker run">
+
+```bash
+docker run -d \
+  --name documenso \
+  -e NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY=your-license-key-here \
+  documenso/documenso:latest
+```
+
+</Tab>
+<Tab value=".env">
+
+If you're running Documenso directly (not in a container), add the variable to your `.env` file:
+
+```bash
+NEXT_PRIVATE_DOCUMENSO_LICENSE_KEY=your-license-key-here
+```
+
+</Tab>
+</Tabs>
+
+## Step 2: Restart the instance
+
+The license key is only read once, at process startup. Setting the variable in a running container or shell has no effect until the process restarts.
+
+```bash
+# Docker Compose
+docker compose restart documenso
+
+# Docker
+docker restart documenso
+```
+
+On startup, Documenso validates the key against the Documenso license server and caches the result locally for future startups, so a brief license-server outage won't lock you out.
+
+## What the license enables
+
+A valid license doesn't turn every enterprise feature on everywhere — activation depends on the feature:
+
+- **CSC signing** activates instance-wide automatically once the license is active and CSC transport is configured. See [CSC / QES Signing](/docs/self-hosting/configuration/signing-certificate/csc-qes) for the full setup.
+- **SSO, embed white-labelling, 21 CFR Part 11, and similar** are provisioned per organisation. Follow each feature's own guide to configure it once the license is active.
+
+## Troubleshooting
+
+<Accordions type="multiple">
+  <Accordion title="Enterprise features are still unavailable after applying the key">
+    - Confirm the key is present in the environment the running process actually reads — `docker
+      exec` into the container and check `env | grep LICENSE` if unsure.
+    - Confirm the instance was fully restarted after the variable was set, not just reloaded.
+    - Re-copy the key to rule out truncation or accidental whitespace.
+  </Accordion>
+  <Accordion title="A specific feature still isn't working">
+    Instance-wide features (like CSC signing) also need their own configuration — an active license
+    alone isn't enough. Check that feature's guide to confirm the required settings are in place.
+    Per-organisation features additionally need to be provisioned for the organisation that's using
+    them.
+  </Accordion>
+</Accordions>
+
+## See Also
+
+- [Environment Variables](/docs/self-hosting/configuration/environment) - Complete configuration reference
+- [Enterprise Edition](/docs/policies/enterprise-edition) - What's included and how to purchase a license
+- [CSC / QES Signing](/docs/self-hosting/configuration/signing-certificate/csc-qes) - Enable CSC-based signing

apps/docs/content/docs/self-hosting/configuration/meta.json

@@ -2,6 +2,7 @@
   "title": "Configuration",
   "pages": [
     "environment",
+    "license",
     "database",
     "email",
     "storage",

apps/docs/content/docs/self-hosting/configuration/signing-certificate/csc-qes.mdx

@@ -49,7 +49,7 @@ The callback URL is fixed — Documenso derives it from `NEXT_PUBLIC_WEBAPP_URL`
 
 ### Enterprise Edition license
 
-CSC mode is gated by the `instanceCscSigning` license flag. Without a valid Enterprise license, the transport refuses to start (`CSC_UNLICENSED`).
+CSC mode is gated by the `instanceCscSigning` license flag. Without a valid Enterprise license, the transport refuses to start (`CSC_UNLICENSED`). See [Apply Your License Key](/docs/self-hosting/configuration/license) to activate one.
 
 </Step>
 <Step>

apps/docs/content/docs/self-hosting/index.mdx

@@ -141,7 +141,7 @@ See the [Quick Start guide](/docs/self-hosting/getting-started/quick-start) for
 
 Self-hosted Documenso includes full core functionality under the AGPL-3.0 license. If you need enterprise features such as SSO, embed editor white label, or 21 CFR Part 11 compliance, you can activate them with a license key.
 
-See [Enterprise Edition](/docs/policies/enterprise-edition) for details and [Licenses](/docs/policies/licenses) for a comparison.
+See [Enterprise Edition](/docs/policies/enterprise-edition) for details and [Licenses](/docs/policies/licenses) for a comparison. Already have a key? See [Apply Your License Key](/docs/self-hosting/configuration/license).
 
 ---
 

apps/docs/content/docs/users/documents/advanced/pdf-placeholders.mdx

@@ -109,6 +109,37 @@ You can customize fields by adding options after the recipient identifier:
 | `maxValue`     | Number        | Maximum allowed value |
 | `numberFormat` | Format string | Number display format |
 
+### Selection Field Options
+
+Checkbox, radio, and dropdown placeholders can define their selectable choices via the `options` property.
+Separate choices with pipe (`|`) characters.
+Checkbox, radio, and dropdown placeholders do not support `label` or `placeholder` metadata.
+
+| Option             | Applies To                | Values                   | Description                              |
+| ------------------ | ------------------------- | ------------------------ | ---------------------------------------- |
+| `options`          | Checkbox, Radio, Dropdown | `Option 1|Option 2`      | Selectable choices                       |
+| `checked`          | Checkbox                  | `Option 1|Option 2`      | Pre-checked choices                      |
+| `selected`         | Radio, Dropdown           | One option value         | Pre-selected/default choice              |
+| `default`          | Radio, Dropdown           | One option value         | Alias for `selected`                     |
+| `defaultValue`     | Radio, Dropdown           | One option value         | Alias for `selected`                     |
+| `direction`        | Checkbox, Radio           | `vertical`, `horizontal` | Option layout                            |
+| `validationRule`   | Checkbox                  | `atLeast`, `exactly`, `atMost` | Checkbox selection validation rule       |
+| `validationLength` | Checkbox                  | Number (e.g., `1`)       | Checkbox validation option count         |
+| `required`         | Checkbox, Radio, Dropdown | `true`, `false`          | Whether the field must be completed      |
+| `readOnly`         | Checkbox, Radio, Dropdown | `true`, `false`          | Whether the pre-selected value is locked |
+| `fontSize`         | Checkbox, Radio, Dropdown | Number (e.g., `12`)      | Field text size                          |
+
+For checkbox validation, `validationLength` defines the option count:
+- `atLeast` means at least that many options must be selected
+- `exactly` means exactly that many options must be selected
+- `atMost` means at most that many options must be selected
+
+If an option needs a literal delimiter, escape it with a backslash:
+
+```
+{{dropdown, r1, options=Sales\|Ops|Legal\, Compliance|A\=B}}
+```
+
 ### Examples with Options
 
 ```
@@ -116,6 +147,10 @@ You can customize fields by adding options after the recipient identifier:
 {{number, r1, minValue=0, maxValue=100, value=50}}
 {{name, r1, fontSize=14}}
 {{text, r2, readOnly=true, text=Contract #12345}}
+{{checkbox, r1, options=Email|SMS|Phone, checked=Email|Phone, validationRule=atLeast, validationLength=1}}
+{{radio, r1, options=Card|Bank transfer|Check, selected=Check}}
+{{dropdown, r1, options=United States|Canada|United Kingdom}}
+{{dropdown, r2, options=Sales|Legal|Finance, defaultValue=Legal}}
 ```
 
 <Callout type="info">

apps/remix/app/components/tables/internal-audit-log-table.tsx

@@ -1,20 +1,48 @@
 import { APP_I18N_OPTIONS } from '@documenso/lib/constants/i18n';
-import type { TDocumentAuditLog } from '@documenso/lib/types/document-audit-logs';
+import { DOCUMENT_AUDIT_LOG_TYPE, type TDocumentAuditLog } from '@documenso/lib/types/document-audit-logs';
 import { formatDocumentAuditLogAction } from '@documenso/lib/utils/document-audit-logs';
+import { cn } from '@documenso/ui/lib/utils';
+import { Card, CardContent } from '@documenso/ui/primitives/card';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
+import type { DateTimeFormatOptions } from 'luxon';
 import { DateTime } from 'luxon';
+import { match, P } from 'ts-pattern';
 import { UAParser } from 'ua-parser-js';
 
 export type AuditLogDataTableProps = {
   logs: TDocumentAuditLog[];
 };
 
+const dateFormat: DateTimeFormatOptions = {
+  ...DateTime.DATETIME_SHORT,
+  hourCycle: 'h12',
+};
+
+/**
+ * Get the color indicator for the audit log type
+ */
+
+const getAuditLogIndicatorColor = (type: string) =>
+  match(type)
+    .with(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_RECIPIENT_COMPLETED, () => 'bg-green-500')
+    .with(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_RECIPIENT_REJECTED, () => 'bg-red-500')
+    .with(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_SENT, () => 'bg-orange-500')
+    .with(
+      P.union(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_FIELD_INSERTED, DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_FIELD_UNINSERTED),
+      () => 'bg-blue-500',
+    )
+    .otherwise(() => 'bg-muted');
+
 /**
  * DO NOT USE TRANS. YOU MUST USE _ FOR THIS FILE AND ALL CHILDREN COMPONENTS.
  */
 
-const formatUserAgent = (userAgent: string, userAgentInfo: UAParser.IResult) => {
+const formatUserAgent = (userAgent: string | null | undefined, userAgentInfo: UAParser.IResult) => {
+  if (!userAgent) {
+    return msg`N/A`;
+  }
+
   const browser = userAgentInfo.browser.name;
   const version = userAgentInfo.browser.version;
   const os = userAgentInfo.os.name;
@@ -35,45 +63,74 @@ export const InternalAuditLogTable = ({ logs }: AuditLogDataTableProps) => {
   const parser = new UAParser();
 
   return (
-    <div className="divide-y divide-border">
+    <div className="space-y-4">
       {logs.map((log, index) => {
         parser.setUA(log.userAgent || '');
         const formattedAction = formatDocumentAuditLogAction(i18n, log);
         const userAgentInfo = parser.getResult();
 
-        const createdAt = DateTime.fromJSDate(log.createdAt).setLocale(APP_I18N_OPTIONS.defaultLocale);
-
-        const metaSegments = [
-          log.email,
-          log.ipAddress,
-          log.userAgent ? _(formatUserAgent(log.userAgent, userAgentInfo)) : null,
-        ].filter((segment): segment is string => Boolean(segment));
-
         return (
-          <div
+          <Card
             key={index}
-            className="flex gap-5 py-2.5"
+            // Add top margin for the first card to ensure it's not cut off from the 2nd page onwards
+            className={`border shadow-sm ${index > 0 ? 'print:mt-8' : ''}`}
             style={{
               pageBreakInside: 'avoid',
               breakInside: 'avoid',
             }}
           >
-            <div className="w-[5.5rem] shrink-0">
-              <div className="text-foreground text-xs">{createdAt.toFormat('yyyy-MM-dd')}</div>
+            <CardContent className="p-4">
+              {/* Header Section with indicator, event type, and timestamp */}
+              <div className="mb-3 flex items-start justify-between">
+                <div className="flex items-baseline gap-3">
+                  <div className={cn(`h-2 w-2 rounded-full`, getAuditLogIndicatorColor(log.type))} />
 
-              <div className="mt-0.5 text-[0.6875rem] text-muted-foreground">{createdAt.toFormat('hh:mm:ss a')}</div>
-            </div>
+                  <div>
+                    <div className="font-medium text-muted-foreground text-sm uppercase tracking-wide print:text-[8pt]">
+                      {log.type.replace(/_/g, ' ')}
+                    </div>
 
-            <div className="min-w-0 flex-1">
-              <div className="text-pretty text-foreground text-sm print:text-xs">{formattedAction.description}</div>
-
-              {metaSegments.length > 0 && (
-                <div className="mt-1 break-words text-muted-foreground text-xs print:text-[0.6875rem]">
-                  {metaSegments.join(' · ')}
+                    <div className="font-medium text-foreground text-sm print:text-[8pt]">
+                      {formattedAction.description}
+                    </div>
+                  </div>
                 </div>
-              )}
-            </div>
-          </div>
+
+                <div className="text-muted-foreground text-sm print:text-[8pt]">
+                  {DateTime.fromJSDate(log.createdAt)
+                    .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                    .toLocaleString(dateFormat)}
+                </div>
+              </div>
+
+              <hr className="my-4" />
+
+              {/* Details Section - Two column layout */}
+              <div className="grid grid-cols-2 gap-x-8 gap-y-2 text-xs print:text-[6pt]">
+                <div>
+                  <div className="font-medium text-muted-foreground/70 uppercase tracking-wide">{_(msg`User`)}</div>
+
+                  <div className="mt-1 font-mono text-foreground">{log.email || 'N/A'}</div>
+                </div>
+
+                <div className="text-right">
+                  <div className="font-medium text-muted-foreground/70 uppercase tracking-wide">
+                    {_(msg`IP Address`)}
+                  </div>
+
+                  <div className="mt-1 font-mono text-foreground">{log.ipAddress || 'N/A'}</div>
+                </div>
+
+                <div className="col-span-2">
+                  <div className="font-medium text-muted-foreground/70 uppercase tracking-wide">
+                    {_(msg`User Agent`)}
+                  </div>
+
+                  <div className="mt-1 text-foreground">{_(formatUserAgent(log.userAgent, userAgentInfo))}</div>
+                </div>
+              </div>
+            </CardContent>
+          </Card>
         );
       })}
     </div>

apps/remix/app/routes/_internal+/[__htmltopdf]+/audit-log.tsx

@@ -7,6 +7,7 @@ import { findDocumentAuditLogs } from '@documenso/lib/server-only/document/find-
 import { getOrganisationClaimByTeamId } from '@documenso/lib/server-only/organisation/get-organisation-claims';
 import { mapSecondaryIdToDocumentId } from '@documenso/lib/utils/envelope';
 import { getTranslations } from '@documenso/lib/utils/i18n';
+import { Card, CardContent } from '@documenso/ui/primitives/card';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { EnvelopeType } from '@prisma/client';
@@ -105,86 +106,82 @@ export default function AuditLog({ loaderData }: Route.ComponentProps) {
 
   return (
     <div className="print-provider pointer-events-none mx-auto max-w-screen-md">
-      <header>
-        <h1 className="font-semibold text-lg tracking-tight">{_(msg`Audit Log`)}</h1>
+      <div className="mb-6 border-b pb-4">
+        <h1 className="font-semibold text-xl">{_(msg`Audit Log`)}</h1>
+      </div>
 
-        <p className="mt-1 text-pretty text-muted-foreground text-sm">{document.title}</p>
-      </header>
+      <Card>
+        <CardContent className="grid grid-cols-2 gap-4 p-6 text-sm print:text-xs">
+          <p>
+            <span className="font-medium">{_(msg`Envelope ID`)}</span>
 
-      <dl className="mt-6 grid grid-cols-2 gap-x-8 gap-y-5">
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Envelope ID`)}</dt>
+            <span className="mt-1 block break-words">{document.envelopeId}</span>
+          </p>
 
-          <dd className="mt-1 break-all text-foreground text-sm print:text-xs">{document.envelopeId}</dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Enclosed Document`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Owner`)}</dt>
+            <span className="mt-1 block break-words">{document.title}</span>
+          </p>
 
-          <dd className="mt-1 break-words text-foreground text-sm print:text-xs">
-            {document.user.name} ({document.user.email})
-          </dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Status`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Status`)}</dt>
+            <span className="mt-1 block">
+              {_(document.deletedAt ? msg`Deleted` : DOCUMENT_STATUS[document.status].description).toUpperCase()}
+            </span>
+          </p>
 
-          <dd className="mt-1 text-foreground text-sm print:text-xs">
-            {_(document.deletedAt ? msg`Deleted` : DOCUMENT_STATUS[document.status].description)}
-          </dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Owner`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Time Zone`)}</dt>
+            <span className="mt-1 block break-words">
+              {document.user.name} ({document.user.email})
+            </span>
+          </p>
 
-          <dd className="mt-1 break-words text-foreground text-sm print:text-xs">
-            {document.documentMeta?.timezone ?? 'N/A'}
-          </dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Created At`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Created At`)}</dt>
+            <span className="mt-1 block">
+              {DateTime.fromJSDate(document.createdAt)
+                .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')}
+            </span>
+          </p>
 
-          <dd className="mt-1 text-foreground text-sm print:text-xs">
-            {DateTime.fromJSDate(document.createdAt)
-              .setLocale(APP_I18N_OPTIONS.defaultLocale)
-              .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')}
-          </dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Last Updated`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Last Updated`)}</dt>
+            <span className="mt-1 block">
+              {DateTime.fromJSDate(document.updatedAt)
+                .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')}
+            </span>
+          </p>
 
-          <dd className="mt-1 text-foreground text-sm print:text-xs">
-            {DateTime.fromJSDate(document.updatedAt)
-              .setLocale(APP_I18N_OPTIONS.defaultLocale)
-              .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')}
-          </dd>
-        </div>
+          <p>
+            <span className="font-medium">{_(msg`Time Zone`)}</span>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Enclosed Document`)}</dt>
+            <span className="mt-1 block break-words">{document.documentMeta?.timezone ?? 'N/A'}</span>
+          </p>
 
-          <dd className="mt-1 break-words text-foreground text-sm print:text-xs">{document.title}</dd>
-        </div>
+          <div>
+            <p className="font-medium">{_(msg`Recipients`)}</p>
 
-        <div>
-          <dt className="font-medium text-muted-foreground text-xs">{_(msg`Recipients`)}</dt>
-
-          <dd className="mt-1 text-foreground text-sm print:text-xs">
-            <ul className="space-y-0.5">
+            <ul className="mt-1 list-inside list-disc">
               {document.recipients.map((recipient) => (
-                <li key={recipient.id} className="break-words">
-                  {recipient.name} ({recipient.email}) ·{' '}
+                <li key={recipient.id}>
                   <span className="text-muted-foreground">
-                    {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
-                  </span>
+                    [{_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}]
+                  </span>{' '}
+                  {recipient.name} ({recipient.email})
                 </li>
               ))}
             </ul>
-          </dd>
-        </div>
-      </dl>
+          </div>
+        </CardContent>
+      </Card>
 
       <div className="mt-8">
         <InternalAuditLogTable logs={auditLogs} />

apps/remix/app/routes/_internal+/[__htmltopdf]+/certificate.tsx

@@ -9,8 +9,11 @@ import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-log
 import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
 import { mapSecondaryIdToDocumentId } from '@documenso/lib/utils/envelope';
 import { getTranslations } from '@documenso/lib/utils/i18n';
+import { Card, CardContent } from '@documenso/ui/primitives/card';
+import { Table, TableBody, TableCell, TableHead, TableHeader, TableRow } from '@documenso/ui/primitives/table';
 import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
 import { EnvelopeType, FieldType, SigningStatus } from '@prisma/client';
 import { DateTime } from 'luxon';
 import { redirect } from 'react-router';
@@ -200,178 +203,165 @@ export default function SigningCertificate({ loaderData }: Route.ComponentProps)
 
   return (
     <div className="print-provider pointer-events-none mx-auto max-w-screen-md">
-      <header>
-        <h1 className="font-semibold text-lg tracking-tight">{_(msg`Signing Certificate`)}</h1>
+      <div className="flex items-center">
+        <h1 className="my-8 font-bold text-2xl">{_(msg`Signing Certificate`)}</h1>
+      </div>
 
-        <p className="mt-1 text-pretty text-muted-foreground text-sm">{document.title}</p>
-      </header>
+      <Card>
+        <CardContent className="p-0">
+          <Table overflowHidden>
+            <TableHeader>
+              <TableRow>
+                <TableHead>{_(msg`Signer Events`)}</TableHead>
+                <TableHead>{_(msg`Signature`)}</TableHead>
+                <TableHead>{_(msg`Details`)}</TableHead>
+                {/* <TableHead>Security</TableHead> */}
+              </TableRow>
+            </TableHeader>
 
-      <table className="mt-6 w-full">
-        <thead>
-          <tr className="border-border border-b">
-            <th className="w-[30%] pr-4 pb-2 text-left font-medium text-muted-foreground text-xs">
-              {_(msg`Signer Events`)}
-            </th>
+            <TableBody className="print:text-xs">
+              {document.recipients.map((recipient, i) => {
+                const logs = getRecipientAuditLogs(recipient.id);
+                const signature = getRecipientSignatureField(recipient.id);
 
-            <th className="w-[30%] pr-4 pb-2 text-left font-medium text-muted-foreground text-xs">
-              {_(msg`Signature`)}
-            </th>
+                return (
+                  <TableRow key={i} className="print:break-inside-avoid">
+                    <TableCell truncate={false} className="w-[min-content] max-w-[220px] align-top">
+                      <div className="hyphens-auto break-words font-medium">{recipient.name}</div>
+                      <div className="break-all">{recipient.email}</div>
+                      <p className="mt-2 text-muted-foreground text-sm print:text-xs">
+                        {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
+                      </p>
 
-            <th className="pb-2 text-left font-medium text-muted-foreground text-xs">{_(msg`Details`)}</th>
-          </tr>
-        </thead>
+                      <p className="mt-2 text-muted-foreground text-sm print:text-xs">
+                        <span className="font-medium">{_(msg`Authentication Level`)}:</span>{' '}
+                        <span className="block">{getAuthenticationLevel(recipient.id)}</span>
+                      </p>
+                    </TableCell>
 
-        <tbody className="divide-y divide-border">
-          {document.recipients.map((recipient, i) => {
-            const logs = getRecipientAuditLogs(recipient.id);
-            const signature = getRecipientSignatureField(recipient.id);
-            const isRejected = Boolean(logs.DOCUMENT_RECIPIENT_REJECTED[0]);
+                    <TableCell truncate={false} className="w-[min-content] align-top">
+                      {signature ? (
+                        <>
+                          <div
+                            className="inline-block rounded-lg p-1"
+                            style={{
+                              boxShadow: `0px 0px 0px 4.88px rgba(122, 196, 85, 0.1), 0px 0px 0px 1.22px rgba(122, 196, 85, 0.6), 0px 0px 0px 0.61px rgba(122, 196, 85, 1)`,
+                            }}
+                          >
+                            {signature.signature?.signatureImageAsBase64 && (
+                              <img
+                                src={`${signature.signature?.signatureImageAsBase64}`}
+                                alt="Signature"
+                                className="max-h-12 max-w-full"
+                              />
+                            )}
 
-            return (
-              <tr key={i} className="align-top print:break-inside-avoid">
-                <td className="py-3 pr-4">
-                  <div className="hyphens-auto break-words font-medium text-sm print:text-xs">{recipient.name}</div>
+                            {signature.signature?.typedSignature && (
+                              <p className="text-center font-signature text-sm">
+                                {signature.signature?.typedSignature}
+                              </p>
+                            )}
+                          </div>
 
-                  <div className="break-all text-muted-foreground text-xs">{recipient.email}</div>
-
-                  <div className="mt-0.5 text-muted-foreground text-xs">
-                    {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
-                  </div>
-
-                  <div className="mt-2.5">
-                    <div className="font-medium text-muted-foreground text-xs">{_(msg`Authentication Level`)}</div>
-
-                    <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                      {getAuthenticationLevel(recipient.id)}
-                    </div>
-                  </div>
-                </td>
-
-                <td className="py-3 pr-4">
-                  {signature ? (
-                    <div className="space-y-2.5">
-                      {!isRejected && (
-                        <div
-                          className="inline-block rounded-lg p-1"
-                          style={{
-                            boxShadow: `0px 0px 0px 4.88px rgba(122, 196, 85, 0.1), 0px 0px 0px 1.22px rgba(122, 196, 85, 0.6), 0px 0px 0px 0.61px rgba(122, 196, 85, 1)`,
-                          }}
-                        >
-                          {signature.signature?.signatureImageAsBase64 && (
-                            <img
-                              src={`${signature.signature?.signatureImageAsBase64}`}
-                              alt="Signature"
-                              className="max-h-12 max-w-full"
-                            />
-                          )}
-
-                          {signature.signature?.typedSignature && (
-                            <p className="text-center font-signature text-sm">{signature.signature?.typedSignature}</p>
-                          )}
-                        </div>
+                          <p className="mt-2 text-muted-foreground text-sm print:text-xs">
+                            <span className="font-medium">{_(msg`Signature ID`)}:</span>{' '}
+                            <span className="block font-mono uppercase">{signature.secondaryId}</span>
+                          </p>
+                        </>
+                      ) : (
+                        <p className="text-muted-foreground">
+                          <Trans>N/A</Trans>
+                        </p>
                       )}
 
-                      <div>
-                        <div className="font-medium text-muted-foreground text-xs">{_(msg`Signature ID`)}</div>
+                      <p className="mt-2 text-muted-foreground text-sm print:text-xs">
+                        <span className="font-medium">{_(msg`IP Address`)}:</span>{' '}
+                        <span className="inline-block">
+                          {logs.DOCUMENT_RECIPIENT_COMPLETED[0]?.ipAddress ?? _(msg`Unknown`)}
+                        </span>
+                      </p>
 
-                        <div className="mt-0.5 break-all font-mono text-xs uppercase">{signature.secondaryId}</div>
+                      <p className="mt-1 text-muted-foreground text-sm print:text-xs">
+                        <span className="font-medium">{_(msg`Device`)}:</span>{' '}
+                        <span className="inline-block">
+                          {getDevice(logs.DOCUMENT_RECIPIENT_COMPLETED[0]?.userAgent)}
+                        </span>
+                      </p>
+                    </TableCell>
+
+                    <TableCell truncate={false} className="w-[min-content] align-top">
+                      <div className="space-y-1">
+                        <p className="text-muted-foreground text-sm print:text-xs">
+                          <span className="font-medium">{_(msg`Sent`)}:</span>{' '}
+                          <span className="inline-block">
+                            {logs.EMAIL_SENT[0]
+                              ? DateTime.fromJSDate(logs.EMAIL_SENT[0].createdAt)
+                                  .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                                  .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
+                              : logs.DOCUMENT_SENT[0]
+                                ? DateTime.fromJSDate(logs.DOCUMENT_SENT[0].createdAt)
+                                    .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                                    .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
+                                : _(msg`Unknown`)}
+                          </span>
+                        </p>
+
+                        <p className="text-muted-foreground text-sm print:text-xs">
+                          <span className="font-medium">{_(msg`Viewed`)}:</span>{' '}
+                          <span className="inline-block">
+                            {logs.DOCUMENT_OPENED[0]
+                              ? DateTime.fromJSDate(logs.DOCUMENT_OPENED[0].createdAt)
+                                  .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                                  .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
+                              : _(msg`Unknown`)}
+                          </span>
+                        </p>
+
+                        {logs.DOCUMENT_RECIPIENT_REJECTED[0] ? (
+                          <p className="text-muted-foreground text-sm print:text-xs">
+                            <span className="font-medium">{_(msg`Rejected`)}:</span>{' '}
+                            <span className="inline-block">
+                              {logs.DOCUMENT_RECIPIENT_REJECTED[0]
+                                ? DateTime.fromJSDate(logs.DOCUMENT_RECIPIENT_REJECTED[0].createdAt)
+                                    .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                                    .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
+                                : _(msg`Unknown`)}
+                            </span>
+                          </p>
+                        ) : (
+                          <p className="text-muted-foreground text-sm print:text-xs">
+                            <span className="font-medium">{_(msg`Signed`)}:</span>{' '}
+                            <span className="inline-block">
+                              {logs.DOCUMENT_RECIPIENT_COMPLETED[0]
+                                ? DateTime.fromJSDate(logs.DOCUMENT_RECIPIENT_COMPLETED[0].createdAt)
+                                    .setLocale(APP_I18N_OPTIONS.defaultLocale)
+                                    .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
+                                : _(msg`Unknown`)}
+                            </span>
+                          </p>
+                        )}
+
+                        <p className="text-muted-foreground text-sm print:text-xs">
+                          <span className="font-medium">{_(msg`Reason`)}:</span>{' '}
+                          <span className="inline-block">
+                            {recipient.signingStatus === SigningStatus.REJECTED
+                              ? recipient.rejectionReason
+                              : _(
+                                  isOwner(recipient.email)
+                                    ? FRIENDLY_SIGNING_REASONS['__OWNER__']
+                                    : FRIENDLY_SIGNING_REASONS[recipient.role],
+                                )}
+                          </span>
+                        </p>
                       </div>
-                    </div>
-                  ) : (
-                    <p className="text-muted-foreground text-sm print:text-xs">{_(msg`N/A`)}</p>
-                  )}
-
-                  <div className="mt-2.5">
-                    <div className="font-medium text-muted-foreground text-xs">{_(msg`IP Address`)}</div>
-
-                    <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                      {logs.DOCUMENT_RECIPIENT_COMPLETED[0]?.ipAddress ?? _(msg`Unknown`)}
-                    </div>
-                  </div>
-
-                  <div className="mt-2.5">
-                    <div className="font-medium text-muted-foreground text-xs">{_(msg`Device`)}</div>
-
-                    <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                      {getDevice(logs.DOCUMENT_RECIPIENT_COMPLETED[0]?.userAgent)}
-                    </div>
-                  </div>
-                </td>
-
-                <td className="py-3">
-                  <div className="space-y-2.5">
-                    <div>
-                      <div className="font-medium text-muted-foreground text-xs">{_(msg`Sent`)}</div>
-
-                      <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                        {logs.EMAIL_SENT[0]
-                          ? DateTime.fromJSDate(logs.EMAIL_SENT[0].createdAt)
-                              .setLocale(APP_I18N_OPTIONS.defaultLocale)
-                              .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
-                          : logs.DOCUMENT_SENT[0]
-                            ? DateTime.fromJSDate(logs.DOCUMENT_SENT[0].createdAt)
-                                .setLocale(APP_I18N_OPTIONS.defaultLocale)
-                                .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
-                            : _(msg`Unknown`)}
-                      </div>
-                    </div>
-
-                    <div>
-                      <div className="font-medium text-muted-foreground text-xs">{_(msg`Viewed`)}</div>
-
-                      <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                        {logs.DOCUMENT_OPENED[0]
-                          ? DateTime.fromJSDate(logs.DOCUMENT_OPENED[0].createdAt)
-                              .setLocale(APP_I18N_OPTIONS.defaultLocale)
-                              .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
-                          : _(msg`Unknown`)}
-                      </div>
-                    </div>
-
-                    {logs.DOCUMENT_RECIPIENT_REJECTED[0] ? (
-                      <div>
-                        <div className="font-medium text-red-600 text-xs">{_(msg`Rejected`)}</div>
-
-                        <div className="mt-0.5 text-red-600 text-sm print:text-xs">
-                          {DateTime.fromJSDate(logs.DOCUMENT_RECIPIENT_REJECTED[0].createdAt)
-                            .setLocale(APP_I18N_OPTIONS.defaultLocale)
-                            .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')}
-                        </div>
-                      </div>
-                    ) : (
-                      <div>
-                        <div className="font-medium text-muted-foreground text-xs">{_(msg`Signed`)}</div>
-
-                        <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                          {logs.DOCUMENT_RECIPIENT_COMPLETED[0]
-                            ? DateTime.fromJSDate(logs.DOCUMENT_RECIPIENT_COMPLETED[0].createdAt)
-                                .setLocale(APP_I18N_OPTIONS.defaultLocale)
-                                .toFormat('yyyy-MM-dd hh:mm:ss a (ZZZZ)')
-                            : _(msg`Unknown`)}
-                        </div>
-                      </div>
-                    )}
-
-                    <div>
-                      <div className="font-medium text-muted-foreground text-xs">{_(msg`Reason`)}</div>
-
-                      <div className="mt-0.5 text-foreground text-sm print:text-xs">
-                        {recipient.signingStatus === SigningStatus.REJECTED
-                          ? recipient.rejectionReason
-                          : _(
-                              isOwner(recipient.email)
-                                ? FRIENDLY_SIGNING_REASONS['__OWNER__']
-                                : FRIENDLY_SIGNING_REASONS[recipient.role],
-                            )}
-                      </div>
-                    </div>
-                  </div>
-                </td>
-              </tr>
-            );
-          })}
-        </tbody>
-      </table>
+                    </TableCell>
+                  </TableRow>
+                );
+              })}
+            </TableBody>
+          </Table>
+        </CardContent>
+      </Card>
 
       {!hidePoweredBy && (
         <div className="my-8 flex-row-reverse space-y-4">
@@ -387,7 +377,7 @@ export default function SigningCertificate({ loaderData }: Route.ComponentProps)
           </div>
 
           <div className="flex items-end justify-end gap-x-4">
-            <p className="flex-shrink-0 font-medium text-muted-foreground text-xs">
+            <p className="flex-shrink-0 font-medium text-sm print:text-xs">
               {_(msg`Signing certificate provided by`)}:
             </p>
             <BrandingLogo className="max-h-6 print:max-h-4" />

apps/remix/package.json

@@ -36,8 +36,8 @@
     "@lingui/react": "^5.6.0",
     "@oslojs/crypto": "^1.0.1",
     "@oslojs/encoding": "^1.1.0",
-    "@react-router/node": "^7.12.0",
-    "@react-router/serve": "^7.12.0",
+    "@react-router/node": "^7.18.1",
+    "@react-router/serve": "^7.18.1",
     "@simplewebauthn/browser": "^13.2.2",
     "@simplewebauthn/server": "^13.2.2",
     "@tanstack/react-query": "5.90.10",
@@ -81,8 +81,8 @@
     "@babel/preset-typescript": "^7.28.5",
     "@lingui/babel-plugin-lingui-macro": "^5.6.0",
     "@lingui/vite-plugin": "^5.6.0",
-    "@react-router/dev": "^7.12.0",
-    "@react-router/remix-routes-option-adapter": "^7.12.0",
+    "@react-router/dev": "^7.18.1",
+    "@react-router/remix-routes-option-adapter": "^7.18.1",
     "@rollup/plugin-babel": "^6.1.0",
     "@rollup/plugin-commonjs": "^28.0.9",
     "@rollup/plugin-json": "^6.1.0",

packages/lib/server-only/envelope-item/create-envelope-items.ts

@@ -57,7 +57,10 @@ export const UNSAFE_createEnvelopeItems = async ({
         flattenForm: envelope.type !== 'TEMPLATE',
       });
 
-      const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized);
+      const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized, {
+        envelopeId: envelope.id,
+        fileName: file.name,
+      });
 
       const { documentData } = await putPdfFileServerSide({
         name: file.name,

packages/lib/server-only/envelope-item/replace-envelope-item-pdf.ts

@@ -85,7 +85,10 @@ export const UNSAFE_replaceEnvelopeItemPdf = async ({
     flattenForm: envelope.type !== 'TEMPLATE',
   });
 
-  const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized);
+  const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized, {
+    envelopeId: envelope.id,
+    fileName: data.file.name,
+  });
 
   // Upload the new PDF and get a new DocumentData record.
   const { documentData: newDocumentData, filePageCount } = await putPdfFileServerSide({

packages/lib/server-only/pdf/auto-place-fields.ts

@@ -1,8 +1,15 @@
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
 import { type TFieldAndMeta, ZEnvelopeFieldAndMetaSchema } from '@documenso/lib/types/field-meta';
+import { logger } from '@documenso/lib/utils/logger';
 import { PDF, rgb } from '@libpdf/core';
 import type { FieldType, Recipient } from '@prisma/client';
 
-import { parseFieldMetaFromPlaceholder, parseFieldTypeFromPlaceholder } from './helpers';
+import {
+  parseFieldMetaFromPlaceholder,
+  parseFieldTypeFromPlaceholder,
+  parsePlaceholderData,
+  parseRawFieldMetaFromPlaceholder,
+} from './helpers';
 
 const PLACEHOLDER_REGEX = /\{\{([^}]+)\}\}/g;
 const DEFAULT_FIELD_HEIGHT_PERCENT = 2;
@@ -61,7 +68,15 @@ export type FieldToCreate = TFieldAndMeta & {
   height: number;
 };
 
-export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<PlaceholderInfo[]> => {
+type ExtractPlaceholdersLogContext = {
+  envelopeId?: string;
+  fileName?: string;
+};
+
+export const extractPlaceholdersFromPDF = async (
+  pdf: Buffer,
+  logContext?: ExtractPlaceholdersLogContext,
+): Promise<PlaceholderInfo[]> => {
   const pdfDoc = await PDF.load(new Uint8Array(pdf));
 
   const placeholders: PlaceholderInfo[] = [];
@@ -85,7 +100,7 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
         continue;
       }
 
-      const placeholderData = innerMatch[1].split(',').map((property) => property.trim());
+      const placeholderData = parsePlaceholderData(innerMatch[1]);
       const [fieldTypeString, recipientOrMeta, ...fieldMetaData] = placeholderData;
 
       let fieldType: FieldType;
@@ -109,14 +124,51 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
 
       const recipient = recipientOrMeta;
 
-      const rawFieldMeta = Object.fromEntries(fieldMetaData.map((property) => property.split('=')));
+      /*
+        Parse and validate the field metadata. A malformed selection placeholder
+        (e.g. an unknown validation rule or a default value that doesn't match an
+        option) is skipped like an invalid field type rather than aborting the whole
+        upload, which may contain other valid placeholders and files.
+      */
+      let fieldAndMeta: TFieldAndMeta;
 
-      const parsedFieldMeta = parseFieldMetaFromPlaceholder(rawFieldMeta, fieldType);
+      try {
+        const rawFieldMeta = parseRawFieldMetaFromPlaceholder(fieldMetaData);
+        const parsedFieldMeta = parseFieldMetaFromPlaceholder(rawFieldMeta, fieldType);
 
-      const fieldAndMeta: TFieldAndMeta = ZEnvelopeFieldAndMetaSchema.parse({
-        type: fieldType,
-        fieldMeta: parsedFieldMeta,
-      });
+        const parsedFieldAndMeta = ZEnvelopeFieldAndMetaSchema.safeParse({
+          type: fieldType,
+          fieldMeta: parsedFieldMeta,
+        });
+
+        /*
+          Surface schema failures as INVALID_BODY (400) instead of letting the raw
+          ZodError bubble up to the caller as an INTERNAL_SERVER_ERROR (500).
+        */
+        if (!parsedFieldAndMeta.success) {
+          throw new AppError(AppErrorCode.INVALID_BODY, {
+            message: `Invalid field metadata for placeholder "${placeholder}": ${parsedFieldAndMeta.error.message}`,
+          });
+        }
+
+        fieldAndMeta = parsedFieldAndMeta.data;
+      } catch (error) {
+        const appError = AppError.parseError(error);
+
+        logger.warn(
+          {
+            envelopeId: logContext?.envelopeId,
+            fileName: logContext?.fileName,
+            placeholder,
+            page: page.index + 1,
+            code: appError.code,
+            message: appError.message,
+          },
+          'Skipping placeholder with invalid field metadata',
+        );
+
+        continue;
+      }
 
       /*
         LibPDF returns bbox in points with bottom-left origin.
@@ -182,8 +234,9 @@ export const removePlaceholdersFromPDF = async (pdf: Buffer, placeholders?: Plac
  */
 export const extractPdfPlaceholders = async (
   pdf: Buffer,
+  logContext?: ExtractPlaceholdersLogContext,
 ): Promise<{ cleanedPdf: Buffer; placeholders: PlaceholderInfo[] }> => {
-  const placeholders = await extractPlaceholdersFromPDF(pdf);
+  const placeholders = await extractPlaceholdersFromPDF(pdf, logContext);
 
   if (placeholders.length === 0) {
     return { cleanedPdf: pdf, placeholders: [] };

packages/lib/server-only/pdf/generate-certificate-pdf.ts

@@ -137,7 +137,6 @@ export const generateCertificatePdf = async (options: GenerateCertificatePdfOpti
     }),
     envelopeOwner,
     envelopeId: envelope.id,
-    envelopeTitle: envelope.title,
     qrToken: envelope.qrToken,
     hidePoweredBy: organisationClaim.flags.hidePoweredBy ?? false,
     pageWidth,

packages/lib/server-only/pdf/helpers.test.ts

@@ -0,0 +1,235 @@
+import { FieldType } from '@prisma/client';
+import { describe, expect, it } from 'vitest';
+
+import { AppError, AppErrorCode } from '../../errors/app-error';
+import {
+  parseFieldMetaFromPlaceholder,
+  parseFieldTypeFromPlaceholder,
+  parsePlaceholderData,
+  parseRawFieldMetaFromPlaceholder,
+} from './helpers';
+
+const expectInvalidBody = (fn: () => unknown) => {
+  try {
+    fn();
+    expect.unreachable('Expected an AppError to be thrown');
+  } catch (error) {
+    expect(error).toBeInstanceOf(AppError);
+    expect((error as AppError).code).toBe(AppErrorCode.INVALID_BODY);
+  }
+};
+
+describe('parseFieldTypeFromPlaceholder function', () => {
+  it('maps known field type strings to the FieldType enum', () => {
+    expect(parseFieldTypeFromPlaceholder('signature')).toBe(FieldType.SIGNATURE);
+    expect(parseFieldTypeFromPlaceholder('radio')).toBe(FieldType.RADIO);
+    expect(parseFieldTypeFromPlaceholder('checkbox')).toBe(FieldType.CHECKBOX);
+    expect(parseFieldTypeFromPlaceholder('dropdown')).toBe(FieldType.DROPDOWN);
+  });
+
+  it('is case-insensitive and trims surrounding whitespace', () => {
+    expect(parseFieldTypeFromPlaceholder('  SiGnAtUrE  ')).toBe(FieldType.SIGNATURE);
+    expect(parseFieldTypeFromPlaceholder('RADIO')).toBe(FieldType.RADIO);
+  });
+
+  it('throws INVALID_BODY for an unknown field type', () => {
+    expectInvalidBody(() => parseFieldTypeFromPlaceholder('FILE'));
+  });
+});
+
+describe('parsePlaceholderData function', () => {
+  it('splits top-level parts on commas and trims each token', () => {
+    expect(parsePlaceholderData('SIGNATURE, r1, required=true')).toEqual(['SIGNATURE', 'r1', 'required=true']);
+  });
+
+  it('does not split on escaped commas', () => {
+    expect(parsePlaceholderData('dropdown, r1, options=Legal\\, Compliance|Sales')).toEqual([
+      'dropdown',
+      'r1',
+      'options=Legal\\, Compliance|Sales',
+    ]);
+  });
+});
+
+describe('parseRawFieldMetaFromPlaceholder function', () => {
+  it('splits each token into a key/value entry', () => {
+    expect(parseRawFieldMetaFromPlaceholder(['required=true', 'fontSize=12'])).toEqual({
+      required: 'true',
+      fontSize: '12',
+    });
+  });
+
+  it('only splits on the first unescaped equals sign', () => {
+    expect(parseRawFieldMetaFromPlaceholder(['label=a=b'])).toEqual({ label: 'a=b' });
+  });
+
+  it('drops tokens without a value and overwrites duplicate keys with the last', () => {
+    expect(parseRawFieldMetaFromPlaceholder(['required', 'fontSize=12', 'fontSize=14'])).toEqual({
+      fontSize: '14',
+    });
+  });
+});
+
+describe('parseFieldMetaFromPlaceholder function', () => {
+  describe('non-field-meta cases', () => {
+    it('returns undefined for signature and free signature fields', () => {
+      expect(parseFieldMetaFromPlaceholder({ required: 'true' }, FieldType.SIGNATURE)).toBeUndefined();
+      expect(parseFieldMetaFromPlaceholder({}, FieldType.FREE_SIGNATURE)).toBeUndefined();
+    });
+
+    it('returns undefined when there is no metadata', () => {
+      expect(parseFieldMetaFromPlaceholder({}, FieldType.TEXT)).toBeUndefined();
+    });
+  });
+
+  describe('generic metadata', () => {
+    it('coerces required/readOnly to booleans (case-insensitive)', () => {
+      expect(parseFieldMetaFromPlaceholder({ required: 'TRUE', readOnly: 'false' }, FieldType.TEXT)).toEqual({
+        type: 'text',
+        required: true,
+        readOnly: false,
+      });
+    });
+
+    it('coerces numeric properties to numbers', () => {
+      expect(parseFieldMetaFromPlaceholder({ fontSize: '14' }, FieldType.TEXT)).toEqual({
+        type: 'text',
+        fontSize: 14,
+      });
+    });
+
+    it('drops numeric properties that are not a number', () => {
+      const parsed = parseFieldMetaFromPlaceholder({ fontSize: 'abc' }, FieldType.TEXT);
+
+      expect(parsed).toEqual({ type: 'text' });
+      expect(parsed).not.toHaveProperty('fontSize');
+    });
+
+    it('keeps label/placeholder for non-selection fields', () => {
+      expect(parseFieldMetaFromPlaceholder({ label: 'Company Name', placeholder: 'Acme' }, FieldType.TEXT)).toEqual({
+        type: 'text',
+        label: 'Company Name',
+        placeholder: 'Acme',
+      });
+    });
+  });
+
+  describe('radio fields', () => {
+    it('builds stable values from options', () => {
+      expect(parseFieldMetaFromPlaceholder({ options: 'Yes|No|Maybe' }, FieldType.RADIO)).toEqual({
+        type: 'radio',
+        values: [
+          { id: 1, checked: false, value: 'Yes' },
+          { id: 2, checked: false, value: 'No' },
+          { id: 3, checked: false, value: 'Maybe' },
+        ],
+      });
+    });
+
+    it('marks only the selected option as checked', () => {
+      const parsed = parseFieldMetaFromPlaceholder({ options: 'Yes|No|Maybe', selected: 'No' }, FieldType.RADIO);
+
+      expect(parsed).toEqual({
+        type: 'radio',
+        values: [
+          { id: 1, checked: false, value: 'Yes' },
+          { id: 2, checked: true, value: 'No' },
+          { id: 3, checked: false, value: 'Maybe' },
+        ],
+      });
+    });
+
+    it('throws when a default value is provided without options', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ selected: 'No' }, FieldType.RADIO));
+    });
+
+    it('throws when the default value does not match an option', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ options: 'Yes|No', selected: 'Maybe' }, FieldType.RADIO));
+    });
+
+    it('throws when options is empty', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ options: '' }, FieldType.RADIO));
+    });
+  });
+
+  describe('checkbox fields', () => {
+    it('builds values with checked state, validation rule alias and length', () => {
+      const parsed = parseFieldMetaFromPlaceholder(
+        {
+          options: 'Email|SMS|Phone',
+          checked: 'Email|Phone',
+          validationRule: 'atLeast',
+          validationLength: '1',
+        },
+        FieldType.CHECKBOX,
+      );
+
+      expect(parsed).toEqual({
+        type: 'checkbox',
+        validationRule: 'Select at least',
+        validationLength: 1,
+        values: [
+          { id: 1, checked: true, value: 'Email' },
+          { id: 2, checked: false, value: 'SMS' },
+          { id: 3, checked: true, value: 'Phone' },
+        ],
+      });
+    });
+
+    it('throws for an unknown validation rule', () => {
+      expectInvalidBody(() =>
+        parseFieldMetaFromPlaceholder({ options: 'A|B', validationRule: 'nope' }, FieldType.CHECKBOX),
+      );
+    });
+
+    it('throws when checked values are provided without options', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ checked: 'A' }, FieldType.CHECKBOX));
+    });
+
+    it('throws when a checked value does not match an option', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ options: 'A|B', checked: 'C' }, FieldType.CHECKBOX));
+    });
+  });
+
+  describe('dropdown fields', () => {
+    it('builds values and sets a matching default value', () => {
+      expect(
+        parseFieldMetaFromPlaceholder(
+          { options: 'United States|Canada|United Kingdom', defaultValue: 'Canada' },
+          FieldType.DROPDOWN,
+        ),
+      ).toEqual({
+        type: 'dropdown',
+        values: [{ value: 'United States' }, { value: 'Canada' }, { value: 'United Kingdom' }],
+        defaultValue: 'Canada',
+      });
+    });
+
+    it('throws when the default value does not match an option', () => {
+      expectInvalidBody(() => parseFieldMetaFromPlaceholder({ options: 'A|B', defaultValue: 'C' }, FieldType.DROPDOWN));
+    });
+  });
+
+  describe('selection field options parsing', () => {
+    it('trims option values and drops empty entries', () => {
+      expect(parseFieldMetaFromPlaceholder({ options: ' A ||  B  ' }, FieldType.DROPDOWN)).toEqual({
+        type: 'dropdown',
+        values: [{ value: 'A' }, { value: 'B' }],
+      });
+    });
+
+    it('parses escaped delimiters through the full placeholder pipeline', () => {
+      const [, , ...fieldMetaData] = parsePlaceholderData(
+        'dropdown, r1, options=Sales\\|Ops|Legal\\, Compliance|A\\=B',
+      );
+
+      const rawFieldMeta = parseRawFieldMetaFromPlaceholder(fieldMetaData);
+      const parsed = parseFieldMetaFromPlaceholder(rawFieldMeta, FieldType.DROPDOWN);
+
+      expect(parsed).toEqual({
+        type: 'dropdown',
+        values: [{ value: 'Sales|Ops' }, { value: 'Legal, Compliance' }, { value: 'A=B' }],
+      });
+    });
+  });
+});

packages/lib/server-only/pdf/helpers.ts

@@ -45,6 +45,134 @@ type RecipientPlaceholderInfo = {
   recipientIndex: number;
 };
 
+const CHECKBOX_VALIDATION_RULE_BY_ALIAS: Record<string, string> = {
+  atLeast: 'Select at least',
+  exactly: 'Select exactly',
+  atMost: 'Select at most',
+};
+
+/*
+  Split a string on a delimiter, treating `\` as an escape for the next character.
+  Delimiters preceded by `\` are kept in the output instead of splitting (e.g. `\,`, `\=`, `\|`).
+
+  With delimiter ',' (top-level placeholder parts):
+  'radio, r1, options=Card/Check|Bank Transfer, selected=Bank Transfer'
+    -> ['radio', ' r1', ' options=Card/Check|Bank Transfer', ' selected=Bank Transfer']
+
+  With delimiter '=' (split one field metadata token into key + value):
+  'options=Card/Check|Bank Transfer'
+    -> ['options', 'Card/Check|Bank Transfer']
+
+  With delimiter '|' (split option list inside 'options='):
+  'Card/Check|Bank Transfer'
+    -> ['Card/Check', 'Bank Transfer']
+*/
+const splitPlaceholderToken = (value: string, delimiter: string): string[] => {
+  const parts: string[] = [];
+  let currentPart = '';
+
+  for (let index = 0; index < value.length; index++) {
+    const char = value[index];
+    const nextChar = value[index + 1];
+
+    if (char === '\\' && nextChar) {
+      currentPart += char + nextChar;
+      index++;
+      continue;
+    }
+
+    if (char === delimiter) {
+      parts.push(currentPart);
+      currentPart = '';
+      continue;
+    }
+
+    currentPart += char;
+  }
+
+  parts.push(currentPart);
+
+  return parts;
+};
+
+/*
+  Removes the escape backslashes left over after splitting, so \,=, \|, \\ become their literal characters.
+
+  E.g.
+  'Legal\, Compliance' -> 'Legal, Compliance'
+  'Card\|Check'        -> 'Card|Check'
+  'A\=B'               -> 'A=B'
+  'C\D'                -> 'C\D'
+*/
+const unescapePlaceholderValue = (value: string): string => {
+  return value.replace(/\\([,=|\\])/g, '$1');
+};
+
+/*
+  Cleans up a selection option/default after splitting:
+  unescapes literal delimiters, collapses repeated whitespace, and trims the ends.
+
+  E.g.
+  '  Legal\,   Compliance  ' -> 'Legal, Compliance'
+*/
+const normalizePlaceholderSelectionValue = (value: string): string => {
+  return unescapePlaceholderValue(value).replace(/\s+/g, ' ').trim();
+};
+
+/*
+  Split an options string into individual choices.
+  Splits on unescaped '|', then unescapes, trims, and drops empty entries.
+
+  E.g.
+  'Card/Check|Bank Transfer'     -> ['Card/Check', 'Bank Transfer']
+  'Card\\|Check|Bank Transfer'   -> ['Card|Check', 'Bank Transfer']
+*/
+const parsePlaceholderOptions = (value: string): string[] => {
+  return splitPlaceholderToken(value, '|')
+    .map((option) => normalizePlaceholderSelectionValue(option))
+    .filter((option) => option.length > 0);
+};
+
+/*
+  Split a placeholder string into top-level parts (field type, recipient, metadata).
+  Splits on unescaped commas, then trims whitespace.
+
+  E.g.
+  'SIGNATURE, r1, required=true'
+    -> ['SIGNATURE', 'r1', 'required=true']
+*/
+export const parsePlaceholderData = (value: string): string[] => {
+  return splitPlaceholderToken(value, ',').map((token) => token.trim());
+};
+
+/*
+  Transforms the field metadata string array into a record of key/value pairs.
+  Each token is split on the first unescaped '='; tokens with no key or no '=' are dropped.
+
+  E.g.
+  ['required=true', 'fontSize=12', 'label=a=b']
+    -> { required: 'true', fontSize: '12', label: 'a=b' }
+*/
+export const parseRawFieldMetaFromPlaceholder = (fieldMetaData: string[]): Record<string, string> => {
+  const rawFieldMeta: Record<string, string> = {};
+
+  for (const fieldMeta of fieldMetaData) {
+    // Split on the first '=' only; any further '=' stays part of the value (e.g. 'label=a=b').
+    const [rawKey, ...valueParts] = splitPlaceholderToken(fieldMeta, '=');
+
+    if (!rawKey || valueParts.length === 0) {
+      continue;
+    }
+
+    const key = rawKey.trim();
+    const value = valueParts.join('=').trim();
+
+    rawFieldMeta[key] = value;
+  }
+
+  return rawFieldMeta;
+};
+
 /*
   Parse field type string to FieldType enum.
   Normalizes the input (uppercase, trim) and validates it's a valid field type.
@@ -72,6 +200,169 @@ export const parseFieldTypeFromPlaceholder = (fieldTypeString: string): FieldTyp
     });
 };
 
+const getDefaultFieldMetaValue = (rawFieldMeta: Record<string, string>) => {
+  const defaultValue = rawFieldMeta.defaultValue ?? rawFieldMeta.default ?? rawFieldMeta.selected;
+
+  return defaultValue ? normalizePlaceholderSelectionValue(defaultValue) : undefined;
+};
+
+const parseCheckboxValidationRule = (value: string): string => {
+  const validationRule = CHECKBOX_VALIDATION_RULE_BY_ALIAS[value];
+
+  if (!validationRule) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: `Invalid checkbox placeholder validation rule: ${value}`,
+    });
+  }
+
+  return validationRule;
+};
+
+const parseSelectionFieldOptions = (
+  rawFieldMeta: Record<string, string>,
+  fieldType: FieldType,
+): string[] | undefined => {
+  const rawOptions = rawFieldMeta.options;
+
+  if (rawOptions === undefined) {
+    return;
+  }
+
+  const parsedOptions = parsePlaceholderOptions(rawOptions);
+
+  if (parsedOptions.length === 0) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: `${fieldType} placeholder options must contain at least one value`,
+    });
+  }
+
+  return parsedOptions;
+};
+
+const applyRadioFieldOptions = (parsedFieldMeta: Record<string, unknown>, rawFieldMeta: Record<string, string>) => {
+  const options = parseSelectionFieldOptions(rawFieldMeta, FieldType.RADIO);
+  const defaultValue = getDefaultFieldMetaValue(rawFieldMeta);
+
+  if (!options && defaultValue) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: 'Radio placeholder default value requires options',
+    });
+  }
+
+  if (!options) {
+    return;
+  }
+
+  const selectedOptionIndex = defaultValue ? options.findIndex((option) => option === defaultValue) : -1;
+
+  if (defaultValue && selectedOptionIndex === -1) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: `Radio placeholder default value "${defaultValue}" must match one of the options`,
+    });
+  }
+
+  parsedFieldMeta.values = options.map((option, index) => ({
+    id: index + 1,
+    checked: index === selectedOptionIndex,
+    value: option,
+  }));
+};
+
+const applyCheckboxFieldOptions = (parsedFieldMeta: Record<string, unknown>, rawFieldMeta: Record<string, string>) => {
+  const options = parseSelectionFieldOptions(rawFieldMeta, FieldType.CHECKBOX);
+  const checkedValues = rawFieldMeta.checked ? parsePlaceholderOptions(rawFieldMeta.checked) : [];
+
+  if (!options && checkedValues.length > 0) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: 'Checkbox placeholder checked values require options',
+    });
+  }
+
+  if (!options) {
+    return;
+  }
+
+  const unmatchedCheckedValues = checkedValues.filter((checkedValue) => !options.includes(checkedValue));
+
+  if (unmatchedCheckedValues.length > 0) {
+    const unmatchedCheckedValue = unmatchedCheckedValues[0];
+
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: [`Checkbox placeholder checked value "${unmatchedCheckedValue}"`, 'must match one of the options'].join(
+        ' ',
+      ),
+    });
+  }
+
+  parsedFieldMeta.values = options.map((option, index) => ({
+    id: index + 1,
+    checked: checkedValues.includes(option),
+    value: option,
+  }));
+};
+
+const applyDropdownFieldOptions = (parsedFieldMeta: Record<string, unknown>, rawFieldMeta: Record<string, string>) => {
+  const options = parseSelectionFieldOptions(rawFieldMeta, FieldType.DROPDOWN);
+  const defaultValue = getDefaultFieldMetaValue(rawFieldMeta);
+
+  if (!options && defaultValue) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: 'Dropdown placeholder default value requires options',
+    });
+  }
+
+  if (!options) {
+    return;
+  }
+
+  if (defaultValue && !options.includes(defaultValue)) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: `Dropdown placeholder default value "${defaultValue}" must match one of the options`,
+    });
+  }
+
+  parsedFieldMeta.values = options.map((option) => ({
+    value: option,
+  }));
+
+  if (defaultValue) {
+    parsedFieldMeta.defaultValue = defaultValue;
+  }
+};
+
+/*
+  Generic field metadata properties are simple properties consisting of a key and a value.
+  E.g. 'required=true', 'fontSize=12', 'textAlign=left'
+  They don't require special handling.
+
+  Special field metadata properties are complex properties consisting of a key and a value with multiple parts.
+  E.g. 'options=Card/Check|Bank Transfer', 'checked=Card|Check', 'selected=Bank Transfer'
+  They require special handling.
+*/
+const shouldSkipGenericFieldMetaParsing = (property: string, fieldType: FieldType): boolean => {
+  if (property === 'options' || property === 'default' || property === 'selected') {
+    return true;
+  }
+
+  const isSelectionField =
+    fieldType === FieldType.CHECKBOX || fieldType === FieldType.RADIO || fieldType === FieldType.DROPDOWN;
+
+  if (!isSelectionField) {
+    return false;
+  }
+
+  if (
+    property === 'label' ||
+    property === 'placeholder' ||
+    property === 'defaultValue' ||
+    (fieldType === FieldType.CHECKBOX && property === 'checked')
+  ) {
+    return true;
+  }
+
+  return false;
+};
+
 /*
   Transform raw field metadata from placeholder format to schema format.
   Users should provide properly capitalized property names (e.g., readOnly, fontSize, textAlign).
@@ -91,7 +382,7 @@ export const parseFieldMetaFromPlaceholder = (
 
   const fieldTypeString = String(fieldType).toLowerCase();
 
-  const parsedFieldMeta: Record<string, boolean | number | string> = {
+  const parsedFieldMeta: Record<string, unknown> = {
     type: fieldTypeString,
   };
 
@@ -104,24 +395,39 @@ export const parseFieldMetaFromPlaceholder = (
   const rawFieldMetaEntries = Object.entries(rawFieldMeta);
 
   for (const [property, value] of rawFieldMetaEntries) {
+    if (shouldSkipGenericFieldMetaParsing(property, fieldType)) {
+      continue;
+    }
+
+    const unescapedValue = unescapePlaceholderValue(value);
+
     if (property === 'readOnly' || property === 'required') {
-      parsedFieldMeta[property] = value === 'true';
+      parsedFieldMeta[property] = unescapedValue.toLowerCase() === 'true';
+    } else if (property === 'validationRule' && fieldType === FieldType.CHECKBOX) {
+      parsedFieldMeta[property] = parseCheckboxValidationRule(unescapedValue);
     } else if (
       property === 'fontSize' ||
       property === 'maxValue' ||
       property === 'minValue' ||
-      property === 'characterLimit'
+      property === 'characterLimit' ||
+      property === 'validationLength'
     ) {
-      const numValue = Number(value);
+      const numValue = Number(unescapedValue);
 
       if (!Number.isNaN(numValue)) {
         parsedFieldMeta[property] = numValue;
       }
     } else {
-      parsedFieldMeta[property] = value;
+      parsedFieldMeta[property] = unescapedValue;
     }
   }
 
+  match(fieldType)
+    .with(FieldType.RADIO, () => applyRadioFieldOptions(parsedFieldMeta, rawFieldMeta))
+    .with(FieldType.CHECKBOX, () => applyCheckboxFieldOptions(parsedFieldMeta, rawFieldMeta))
+    .with(FieldType.DROPDOWN, () => applyDropdownFieldOptions(parsedFieldMeta, rawFieldMeta))
+    .otherwise(() => undefined);
+
   return parsedFieldMeta;
 };
 

packages/trpc/server/envelope-router/create-envelope.ts

@@ -124,7 +124,9 @@ export const createEnvelopeRouteCaller = async ({
       });
 
       // Todo: Embeds - Might need to add this for client-side embeds in the future.
-      const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized);
+      const { cleanedPdf, placeholders } = await extractPdfPlaceholders(normalized, {
+        fileName: file.name,
+      });
 
       const { documentData } = await putPdfFileServerSide({
         name: file.name,