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

.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`.

.github/actions/node-install/action.yml

@@ -2,7 +2,7 @@ name: 'Setup node'
 inputs:
   node_version:
     required: false
-    default: v24.x
+    default: v22.x
 
 runs:
   using: 'composite'

README.md

@@ -107,7 +107,7 @@ Contact us if you are interested in our Enterprise plan for large organizations
 
 To run Documenso locally, you will need
 
-- Node.js (v24 or above)
+- Node.js (v22 or above)
 - Postgres SQL Database
 - Docker (optional)
 

apps/docs/content/docs/self-hosting/deployment/manual.mdx

@@ -14,8 +14,8 @@ import { Step, Steps } from 'fumadocs-ui/components/steps';
 
 ## Prerequisites
 
-- Node.js 24 or later
-- npm 11.17 or later
+- Node.js 22 or later
+- npm 11 or later
 - PostgreSQL 14 or later
 - A Linux server (for systemd service setup)
 

apps/docs/content/docs/self-hosting/getting-started/requirements.mdx

@@ -141,8 +141,8 @@ If building from source (not using Docker images):
 
 | Requirement | Version |
 | ----------- | ------- |
-| Node.js     | 24+     |
-| npm         | 11.17+  |
+| Node.js     | 22+     |
+| npm         | 11+     |
 
 ---
 
@@ -169,7 +169,7 @@ Documenso runs on:
 | MySQL/MariaDB  | PostgreSQL-specific features required |
 | SQLite         | Not suitable for production workloads |
 | MongoDB        | Relational database required          |
-| Node.js < 24   | Modern JavaScript features required   |
+| Node.js < 22   | Modern JavaScript features required   |
 
 ---
 

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/Dockerfile.bun

@@ -0,0 +1,25 @@
+FROM oven/bun:1 AS dependencies-env
+COPY . /app
+
+FROM dependencies-env AS development-dependencies-env
+COPY ./package.json bun.lockb /app/
+WORKDIR /app
+RUN bun i --frozen-lockfile
+
+FROM dependencies-env AS production-dependencies-env
+COPY ./package.json bun.lockb /app/
+WORKDIR /app
+RUN bun i --production
+
+FROM dependencies-env AS build-env
+COPY ./package.json bun.lockb /app/
+COPY --from=development-dependencies-env /app/node_modules /app/node_modules
+WORKDIR /app
+RUN bun run build
+
+FROM dependencies-env
+COPY ./package.json bun.lockb /app/
+COPY --from=production-dependencies-env /app/node_modules /app/node_modules
+COPY --from=build-env /app/build /app/build
+WORKDIR /app
+CMD ["bun", "run", "start"]

apps/remix/Dockerfile.pnpm

@@ -0,0 +1,26 @@
+FROM node:20-alpine AS dependencies-env
+RUN npm i -g pnpm
+COPY . /app
+
+FROM dependencies-env AS development-dependencies-env
+COPY ./package.json pnpm-lock.yaml /app/
+WORKDIR /app
+RUN pnpm i --frozen-lockfile
+
+FROM dependencies-env AS production-dependencies-env
+COPY ./package.json pnpm-lock.yaml /app/
+WORKDIR /app
+RUN pnpm i --prod --frozen-lockfile
+
+FROM dependencies-env AS build-env
+COPY ./package.json pnpm-lock.yaml /app/
+COPY --from=development-dependencies-env /app/node_modules /app/node_modules
+WORKDIR /app
+RUN pnpm build
+
+FROM dependencies-env
+COPY ./package.json pnpm-lock.yaml /app/
+COPY --from=production-dependencies-env /app/node_modules /app/node_modules
+COPY --from=build-env /app/build /app/build
+WORKDIR /app
+CMD ["pnpm", "start"]

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

@@ -1,7 +1,4 @@
-import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
-import type { TBulkSendCsvError } from '@documenso/lib/server-only/template/validate-bulk-send-csv';
 import { trpc } from '@documenso/trpc/react';
-import { Alert, AlertDescription } from '@documenso/ui/primitives/alert';
 import { Button } from '@documenso/ui/primitives/button';
 import { Checkbox } from '@documenso/ui/primitives/checkbox';
 import {
@@ -20,9 +17,7 @@ import { msg } from '@lingui/core/macro';
 import { useLingui } from '@lingui/react';
 import { Trans } from '@lingui/react/macro';
 import { File as FileIcon, Upload, X } from 'lucide-react';
-import { useState } from 'react';
 import { useForm } from 'react-hook-form';
-import { match } from 'ts-pattern';
 import { z } from 'zod';
 
 import { useCurrentTeam } from '~/providers/team';
@@ -34,8 +29,6 @@ const ZBulkSendFormSchema = z.object({
 
 type TBulkSendFormSchema = z.infer<typeof ZBulkSendFormSchema>;
 
-type TBulkSendValidationError = TBulkSendCsvError | { type: 'UPLOAD_ERROR'; code: string };
-
 export type TemplateBulkSendDialogProps = {
   templateId: number;
   recipients: Array<{ email: string; name?: string | null }>;
@@ -49,9 +42,6 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
 
   const team = useCurrentTeam();
 
-  const [open, setOpen] = useState(false);
-  const [validationError, setValidationError] = useState<TBulkSendValidationError | null>(null);
-
   const form = useForm<TBulkSendFormSchema>({
     resolver: zodResolver(ZBulkSendFormSchema),
     defaultValues: {
@@ -61,20 +51,6 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
 
   const { mutateAsync: uploadBulkSend } = trpc.template.uploadBulkSend.useMutation();
 
-  const onOpenChange = (value: boolean) => {
-    if (form.formState.isSubmitting) {
-      return;
-    }
-
-    setOpen(value);
-
-    if (!value) {
-      setValidationError(null);
-
-      form.reset();
-    }
-  };
-
   const onDownloadTemplate = () => {
     const headers = recipients.flatMap((_, index) => [`recipient_${index + 1}_email`, `recipient_${index + 1}_name`]);
 
@@ -95,44 +71,36 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
   };
 
   const onSubmit = async (values: TBulkSendFormSchema) => {
-    setValidationError(null);
-
     try {
       const csv = await values.file.text();
 
-      const result = await uploadBulkSend({
+      await uploadBulkSend({
         templateId,
         teamId: team?.id,
         csv: csv,
         sendImmediately: values.sendImmediately,
       });
 
-      if (!result.success) {
-        setValidationError(result.error);
-
-        return;
-      }
-
       toast({
         title: _(msg`Success`),
         description: _(msg`Your bulk send has been initiated. You will receive an email notification upon completion.`),
       });
 
-      setOpen(false);
       form.reset();
-
       onSuccess?.();
     } catch (err) {
       console.error(err);
 
-      const error = AppError.parseError(err);
-
-      setValidationError({ type: 'UPLOAD_ERROR', code: error.code });
+      toast({
+        title: _(msg`Error`),
+        description: _(msg`Failed to upload CSV. Please check the file format and try again.`),
+        variant: 'destructive',
+      });
     }
   };
 
   return (
-    <Dialog open={open} onOpenChange={onOpenChange}>
+    <Dialog>
       <DialogTrigger asChild>
         {trigger ?? (
           <Button variant="outline" className="shrink-0" size="sm">
@@ -206,10 +174,7 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
                             className="hidden"
                             onChange={(e) => {
                               const file = e.target.files?.[0];
-
                               if (file) {
-                                setValidationError(null);
-
                                 onChange(file);
                               }
                             }}
@@ -230,11 +195,7 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
                           type="button"
                           variant="link"
                           className="p-0 text-destructive text-xs hover:text-destructive"
-                          onClick={() => {
-                            setValidationError(null);
-
-                            form.resetField('file');
-                          }}
+                          onClick={() => onChange(null)}
                           disabled={form.formState.isSubmitting}
                         >
                           <X className="h-4 w-4" />
@@ -257,67 +218,6 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
               )}
             />
 
-            {validationError !== null && (
-              <Alert variant="destructive">
-                <AlertDescription className="max-h-32 overflow-y-auto">
-                  {match(validationError)
-                    .with({ type: 'PARSE_ERROR' }, () => (
-                      <Trans>The CSV could not be parsed. Please check the file format and try again.</Trans>
-                    ))
-                    .with({ type: 'EMPTY' }, () => (
-                      <Trans>
-                        The CSV does not contain any rows. Please add at least one row of recipient details.
-                      </Trans>
-                    ))
-                    .with({ type: 'ROW_LIMIT_EXCEEDED' }, ({ rowCount, maxRows }) => (
-                      <Trans>
-                        The CSV contains {rowCount} rows. A maximum of {maxRows} rows is allowed per upload.
-                      </Trans>
-                    ))
-                    .with({ type: 'MISSING_COLUMNS' }, ({ missingColumns }) => (
-                      <>
-                        <Trans>
-                          The CSV is missing the following required columns. Please download the template CSV for the
-                          correct format.
-                        </Trans>
-
-                        <ul className="mt-1 list-inside list-disc">
-                          {missingColumns.map((column) => (
-                            <li key={column} className="font-mono">
-                              {column}
-                            </li>
-                          ))}
-                        </ul>
-                      </>
-                    ))
-                    .with({ type: 'INVALID_RECIPIENTS' }, ({ rowErrors }) => (
-                      <>
-                        <Trans>The CSV contains invalid recipient emails. Please fix the following rows:</Trans>
-
-                        <ul className="mt-1 list-inside list-disc">
-                          {rowErrors.map((rowError, index) => (
-                            <li key={index}>
-                              <Trans>
-                                Row {rowError.row}: <span className="font-mono">{rowError.column}</span> must be a valid
-                                email or empty
-                              </Trans>
-                            </li>
-                          ))}
-                        </ul>
-                      </>
-                    ))
-                    .with({ type: 'UPLOAD_ERROR' }, ({ code }) =>
-                      code === AppErrorCode.LIMIT_EXCEEDED ? (
-                        <Trans>The CSV exceeds the maximum file size.</Trans>
-                      ) : (
-                        <Trans>Failed to upload CSV. Please check the file format and try again.</Trans>
-                      ),
-                    )
-                    .exhaustive()}
-                </AlertDescription>
-              </Alert>
-            )}
-
             <FormField
               control={form.control}
               name="sendImmediately"
@@ -340,12 +240,7 @@ export const TemplateBulkSendDialog = ({ templateId, recipients, trigger, onSucc
             />
 
             <DialogFooter className="mt-4">
-              <Button
-                variant="secondary"
-                onClick={() => onOpenChange(false)}
-                disabled={form.formState.isSubmitting}
-                type="button"
-              >
+              <Button variant="secondary" onClick={() => form.reset()} type="button">
                 <Trans>Cancel</Trans>
               </Button>
 

apps/remix/app/entry.server.tsx

@@ -7,11 +7,10 @@ import { createReadableStreamFromReadable } from '@react-router/node';
 import { isbot } from 'isbot';
 import type { RenderToPipeableStreamOptions } from 'react-dom/server';
 import { renderToPipeableStream } from 'react-dom/server';
-import type { EntryContext, RouterContextProvider } from 'react-router';
+import type { AppLoadContext, EntryContext } from 'react-router';
 import { ServerRouter } from 'react-router';
 
 import { langCookie } from './storage/lang-cookie.server';
-import { nonceContext } from './utils/nonce';
 
 export const streamTimeout = 5_000;
 
@@ -20,7 +19,7 @@ export default async function handleRequest(
   responseStatusCode: number,
   responseHeaders: Headers,
   routerContext: EntryContext,
-  loadContext: RouterContextProvider,
+  loadContext: AppLoadContext,
 ) {
   let language = await langCookie.parse(request.headers.get('cookie') ?? '');
 
@@ -34,7 +33,7 @@ export default async function handleRequest(
   // scripts it injects (route manifest, hydration data, module preloads).
   // The same nonce is also exposed to the React tree via the root loader so
   // our own inline scripts/styles can carry it.
-  const nonce = loadContext.get(nonceContext) || undefined;
+  const nonce = loadContext.nonce || undefined;
 
   return new Promise((resolve, reject) => {
     let shellRendered = false;

apps/remix/app/middleware/admin.ts

@@ -1,13 +0,0 @@
-import { getOptionalSession } from '@documenso/auth/server/lib/utils/get-session';
-import { isAdmin } from '@documenso/lib/utils/is-admin';
-import { type MiddlewareFunction, redirect } from 'react-router';
-
-export const adminMiddleware: MiddlewareFunction = async ({ request }, next) => {
-  const { user } = await getOptionalSession(request);
-
-  if (!user || !isAdmin(user)) {
-    throw redirect('/');
-  }
-
-  return next();
-};

apps/remix/app/middleware/nonce.ts

@@ -1,8 +0,0 @@
-import type { MiddlewareFunction } from 'react-router';
-
-import { getRequestNonce } from '../../server/load-context';
-import { nonceContext } from '../utils/nonce';
-
-export const nonceMiddleware: MiddlewareFunction = ({ context }) => {
-  context.set(nonceContext, getRequestNonce());
-};

apps/remix/app/root.tsx

@@ -23,16 +23,13 @@ import {
   useMatches,
 } from 'react-router';
 import { PreventFlashOnWrongTheme, ThemeProvider, useTheme } from 'remix-themes';
-import { nonceMiddleware } from '~/middleware/nonce';
 import type { Route } from './+types/root';
 import stylesheet from './app.css?url';
 import { GenericErrorLayout } from './components/general/generic-error-layout';
 import { langCookie } from './storage/lang-cookie.server';
 import { themeSessionResolver } from './storage/theme-session.server';
 import { appMetaTags } from './utils/meta';
-import { nonce, nonceContext } from './utils/nonce';
-
-export const middleware = [nonceMiddleware];
+import { nonce } from './utils/nonce';
 
 export const links: Route.LinksFunction = () => [{ rel: 'stylesheet', href: stylesheet }];
 
@@ -77,7 +74,7 @@ export async function loader({ context, request }: Route.LoaderArgs) {
       // Surface the per-request CSP nonce produced by `securityHeadersMiddleware` so all
       // SSR-rendered <script>/<style> elements in this layout (and child
       // routes that need it) can carry the matching nonce attribute.
-      nonce: context.get(nonceContext),
+      nonce: context.nonce,
       session: session.isAuthenticated
         ? {
             user: session.user,

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

@@ -1,4 +1,4 @@
-import { getOptionalSession } from '@documenso/auth/server/lib/utils/get-session';
+import { getSession } from '@documenso/auth/server/lib/utils/get-session';
 import { LicenseClient } from '@documenso/lib/server-only/license/license-client';
 import { isAdmin } from '@documenso/lib/utils/is-admin';
 import { cn } from '@documenso/ui/lib/utils';
@@ -20,18 +20,16 @@ import {
 import { Link, Outlet, redirect, useLocation } from 'react-router';
 
 import { AdminLicenseStatusBanner } from '~/components/general/admin-license-status-banner';
-import { adminMiddleware } from '~/middleware/admin';
 import { appMetaTags } from '~/utils/meta';
+
 import type { Route } from './+types/_layout';
 
 export function meta() {
   return appMetaTags(msg`Admin`);
 }
 
-export const middleware = [adminMiddleware];
-
 export async function loader({ request }: Route.LoaderArgs) {
-  const { user } = await getOptionalSession(request);
+  const { user } = await getSession(request);
 
   const license = await LicenseClient.getInstance()?.getCachedLicense();
 

apps/remix/app/routes/api+/certificate-status.ts

@@ -1,8 +1,8 @@
 import { getCertificateStatus } from '@documenso/lib/server-only/cert/cert-status';
 
-export const loader = async () => {
+export const loader = () => {
   try {
-    const certStatus = await getCertificateStatus();
+    const certStatus = getCertificateStatus();
 
     return Response.json({
       isAvailable: certStatus.isAvailable,

apps/remix/app/routes/api+/health.ts

@@ -22,7 +22,7 @@ export const loader = async () => {
   }
 
   try {
-    const certStatus = await getCertificateStatus();
+    const certStatus = getCertificateStatus();
 
     if (certStatus.isAvailable) {
       checks.certificate = { status: 'ok' };

apps/remix/app/utils/nonce.ts

@@ -1,10 +1,4 @@
-import { createContext, useRouteLoaderData } from 'react-router';
-
-/**
- * Per-request CSP nonce. Set by the root route middleware, read with
- * `context.get(nonceContext)` in loaders/actions and `entry.server`.
- */
-export const nonceContext = createContext<string>('');
+import { useRouteLoaderData } from 'react-router';
 
 /**
  * Returns the supplied CSP nonce only when rendering on the server.

apps/remix/package.json

@@ -106,5 +106,5 @@
     "vite-plugin-babel-macros": "^1.0.6",
     "vite-tsconfig-paths": "^5.1.4"
   },
-  "version": "2.18.0"
+  "version": "2.17.0"
 }

apps/remix/react-router.config.ts

@@ -8,7 +8,4 @@ export default {
   // kept without a trailing slash so they match exactly, and so the bare
   // sub-path URL (e.g. "/ESign") still matches the basename at runtime.
   basename: process.env.NEXT_PUBLIC_BASE_PATH ? process.env.NEXT_PUBLIC_BASE_PATH.replace(/\/$/, '') : '/',
-  future: {
-    v8_middleware: true,
-  },
 } satisfies Config;

apps/remix/server/context.ts

@@ -24,11 +24,12 @@ export const appContext = async (c: Context, next: Next) => {
 
   // These are non page paths like API.
   if (!isPageRequest(request) || noSessionCookie || blacklistedPathsRegex.test(url.pathname)) {
-    return await next();
+    return next();
   }
 
   // Add context to any pages you want here.
-  return await next();
+
+  return next();
 };
 
 const setAppContext = (c: Context, context: AppContext) => {

apps/remix/server/load-context.ts

@@ -1,16 +1,33 @@
 import { getContext } from 'hono/context-storage';
-import { RouterContextProvider } from 'react-router';
+import type { AppLoadContext } from 'react-router';
 
 import type { HonoEnv } from './router';
 import { CSP_NONCE_KEY } from './security-headers';
 
 /**
- * Per-request CSP nonce set by `securityHeadersMiddleware`, read via
- * `hono/context-storage` (enabled in `server/router.ts`).
+ * Augment React Router's `AppLoadContext` so loaders, actions, and
+ * `entry.server` can access fields by name without casts.
  */
-export const getRequestNonce = (): string => getContext<HonoEnv>().var[CSP_NONCE_KEY] ?? '';
+declare module 'react-router' {
+  interface AppLoadContext {
+    /**
+     * Per-request CSP nonce. Populated by `securityHeadersMiddleware` and surfaced here
+     * so it can be threaded into `<ServerRouter nonce>` and root loader
+     * data, which then feeds `<Scripts>`, `<Links>`, etc.
+     */
+    nonce: string;
+  }
+}
 
 /**
- * `future.v8_middleware` requires a `RouterContextProvider` instance here.
+ * Builds the React Router `AppLoadContext` for both dev (vite plugin) and
+ * production (`hono-react-router-adapter/node`).
+ *
+ * The Hono context isn't passed directly by the adapter, so we read it via
+ * `hono/context-storage`, which is enabled in `server/router.ts`.
  */
-export const getLoadContext = (): RouterContextProvider => new RouterContextProvider();
+export const getLoadContext = (): AppLoadContext => {
+  const nonce = getContext<HonoEnv>().var[CSP_NONCE_KEY] ?? '';
+
+  return { nonce };
+};

apps/remix/vite.config.ts

@@ -5,7 +5,6 @@ import { lingui } from '@lingui/vite-plugin';
 import { reactRouter } from '@react-router/dev/vite';
 import autoprefixer from 'autoprefixer';
 import serverAdapter from 'hono-react-router-adapter/vite';
-import type { AppLoadContext } from 'react-router';
 import tailwindcss from 'tailwindcss';
 import { defineConfig, normalizePath } from 'vite';
 import macrosPlugin from 'vite-plugin-babel-macros';
@@ -54,7 +53,7 @@ export default defineConfig({
       entry: 'server/router.ts',
       getLoadContext: async () => {
         const { getLoadContext } = await import('./server/load-context');
-        return getLoadContext() as unknown as AppLoadContext;
+        return getLoadContext();
       },
       exclude: [
         // Spread the defaults but replace the /.css$/ rule so that Bull

docker/Dockerfile

@@ -1,7 +1,7 @@
 ###########################
 #     BASE CONTAINER      #
 ###########################
-FROM node:24-alpine3.23 AS base
+FROM node:22-alpine3.22 AS base
 
 RUN apk add --no-cache openssl
 RUN apk add --no-cache font-freefont
@@ -19,10 +19,7 @@ WORKDIR /app
 
 COPY . .
 
-# Install the exact turbo version resolved in the lockfile, without installing
-# the rest of the dependency tree (prune must run before any npm ci).
-RUN TURBO_VERSION="$(jq -r '.packages["node_modules/turbo"].version' package-lock.json)" \
-    && npm install -g "turbo@${TURBO_VERSION}"
+RUN npm install -g "turbo@^2.10.0"
 
 # Outputs to the /out folder
 # source: https://turbo.build/repo/docs/reference/command-line-reference/prune#--docker
@@ -42,9 +39,9 @@ RUN apk add --no-cache make cmake g++ openssl bash
 WORKDIR /app
 
 # Disable husky from installing hooks
-ENV HUSKY=0
-ENV DOCKER_OUTPUT=1
-ENV NEXT_TELEMETRY_DISABLED=1
+ENV HUSKY 0
+ENV DOCKER_OUTPUT 1
+ENV NEXT_TELEMETRY_DISABLED 1
 
 # Encryption keys
 ARG NEXT_PRIVATE_ENCRYPTION_KEY="CAFEBABE"
@@ -88,17 +85,17 @@ COPY --from=builder /app/out/full/ .
 # Finally copy the turbo.json file so that we can run turbo commands
 COPY turbo.json turbo.json
 
-ENV NODE_OPTIONS="--max-old-space-size=8192"
+RUN npm install -g "turbo@^2.10.0"
 
-RUN npx turbo run build --filter=@documenso/remix...
+RUN turbo run build --filter=@documenso/remix...
 
 ###########################
 #     RUNNER CONTAINER    #
 ###########################
 FROM base AS runner
 
-ENV HUSKY=0
-ENV DOCKER_OUTPUT=1
+ENV HUSKY 0
+ENV DOCKER_OUTPUT 1
 
 # Telemetry credentials (baked into image at build time, can be disabled at runtime)
 ARG NEXT_PRIVATE_TELEMETRY_KEY=""
@@ -121,16 +118,7 @@ COPY --from=builder --chown=nodejs:nodejs /app/out/full/packages/tailwind-config
 # Copy the patches across
 COPY --from=builder --chown=nodejs:nodejs /app/patches ./patches
 
-RUN npm ci --omit=dev --no-audit --no-fund && npm cache clean --force
-
-# Strip build-time residue that ships as production dependencies but is never
-# executed at runtime.
-RUN rm -rf \
-    node_modules/react-email/dist/cli \
-    node_modules/esbuild \
-    node_modules/@esbuild \
-    node_modules/.bin/esbuild \
-    node_modules/.bin/email
+RUN npm ci --only=production
 
 # Automatically leverage output traces to reduce image size
 # https://nodejs.org/docs/advanced-features/output-file-tracing
@@ -141,9 +129,8 @@ COPY --from=installer --chown=nodejs:nodejs /app/apps/remix/public ./apps/remix/
 COPY --from=installer --chown=nodejs:nodejs /app/packages/prisma/schema.prisma ./packages/prisma/schema.prisma
 COPY --from=installer --chown=nodejs:nodejs /app/packages/prisma/migrations ./packages/prisma/migrations
 
-# Generate the prisma client again, this time only targeting the client generator
-RUN npx prisma generate --schema ./packages/prisma/schema.prisma --generator client \
-    && npm cache clean --force
+# Generate the prisma client again
+RUN npx prisma generate --schema ./packages/prisma/schema.prisma
 
 
 # Get the start script from docker/

package-lock.json

@@ -1,12 +1,12 @@
 {
   "name": "@documenso/root",
-  "version": "2.18.0",
+  "version": "2.17.0",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "@documenso/root",
-      "version": "2.18.0",
+      "version": "2.17.0",
       "hasInstallScript": true,
       "workspaces": [
         "apps/*",
@@ -102,8 +102,8 @@
         "zod-prisma-types": "3.3.5"
       },
       "engines": {
-        "node": ">=24.0.0",
-        "npm": ">=11.17.0"
+        "node": ">=22.0.0",
+        "npm": ">=11.11.0"
       }
     },
     "apps/docs": {
@@ -416,7 +416,7 @@
     },
     "apps/remix": {
       "name": "@documenso/remix",
-      "version": "2.18.0",
+      "version": "2.17.0",
       "dependencies": {
         "@cantoo/pdf-lib": "^2.5.3",
         "@documenso/api": "*",
@@ -3153,7 +3153,6 @@
       "version": "10.5.0",
       "resolved": "https://registry.npmjs.org/@chevrotain/cst-dts-gen/-/cst-dts-gen-10.5.0.tgz",
       "integrity": "sha512-lhmC/FyqQ2o7pGK4Om+hzuDrm9rhFYIJ/AXoQBeongmn870Xeb0L6oGEiuR8nohFNL5sMaQEJWCxr1oIVIVXrw==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@chevrotain/gast": "10.5.0",
@@ -3165,7 +3164,6 @@
       "version": "10.5.0",
       "resolved": "https://registry.npmjs.org/@chevrotain/gast/-/gast-10.5.0.tgz",
       "integrity": "sha512-pXdMJ9XeDAbgOWKuD1Fldz4ieCs6+nLNmyVhe2gZVqoO7v8HXuHYs5OV2EzUtbuai37TlOAQHrTDvxMnvMJz3A==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@chevrotain/types": "10.5.0",
@@ -3176,14 +3174,12 @@
       "version": "10.5.0",
       "resolved": "https://registry.npmjs.org/@chevrotain/types/-/types-10.5.0.tgz",
       "integrity": "sha512-f1MAia0x/pAVPWH/T73BJVyO2XU5tI4/iE7cnxb7tqdNTNhQI3Uq3XkqcoteTmD4t1aM0LbHCJOhgIDn07kl2A==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@chevrotain/utils": {
       "version": "10.5.0",
       "resolved": "https://registry.npmjs.org/@chevrotain/utils/-/utils-10.5.0.tgz",
       "integrity": "sha512-hBzuU5+JjB2cqNZyszkDHZgOSrUUT8V3dhgRl8Q9Gp6dAj/H5+KILGjbhDpc3Iy9qmqlm/akuOI2ut9VUtzJxQ==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@commitlint/cli": {
@@ -5727,7 +5723,6 @@
       "version": "0.13.1",
       "resolved": "https://registry.npmjs.org/@mrleebo/prisma-ast/-/prisma-ast-0.13.1.tgz",
       "integrity": "sha512-XyroGQXcHrZdvmrGJvsA9KNeOOgGMg1Vg9OlheUsBOSKznLMDl+YChxbkboRHvtFYJEMRYmlV3uoo/njCw05iw==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "chevrotain": "^10.5.0",
@@ -10300,14 +10295,12 @@
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/dmmf/-/dmmf-6.19.3.tgz",
       "integrity": "sha512-+D6v7RIF21bJrZAXiiIdW0qR73TleYVCqTDozokdEHdGeqN997O7jJW5z+43s5CVwWTZJIwFGpoeXxDDyXDVxA==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@prisma/driver-adapter-utils": {
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/driver-adapter-utils/-/driver-adapter-utils-6.19.3.tgz",
       "integrity": "sha512-UUxn6VLfKKVqm5n9vexOQgFJ9TCBIxupb7F5FzLQ6iM2VV0WZxhgzbQVqBDsGY+VmQLmqaSoKRusEfy3O5KZpA==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@prisma/debug": "6.19.3"
@@ -10356,14 +10349,12 @@
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/generator/-/generator-6.19.3.tgz",
       "integrity": "sha512-rzHJaIZEnEDUWNjjFAimsyMCS9osPxwbwiAbymwFprSHJSAglMxMDVU+xbQUCLeDsjUF09W5ag/aBPL2t3YqgA==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@prisma/generator-helper": {
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/generator-helper/-/generator-helper-6.19.3.tgz",
       "integrity": "sha512-13S8ngSWVKcyuRFqaK/JGMyovjQC5sOKJ9A+ufqePQWeIUbvKO2QY2CmhcV4JAa2vuN22//4Sip5mORVKwS0sw==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@prisma/debug": "6.19.3",
@@ -10384,7 +10375,6 @@
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/internals/-/internals-6.19.3.tgz",
       "integrity": "sha512-1V5ba+BNtGFFlgoA8ecyAbjmoMWzIrEuebmLbJpeS7qbhnY6vbc1OZ6qc55lI/VAkfdALSL5vePG5KF9P8feLw==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@prisma/config": "6.19.3",
@@ -10415,21 +10405,18 @@
       "version": "7.1.1-3.c2990dca591cba766e3b7ef5d9e8a84796e47ab7",
       "resolved": "https://registry.npmjs.org/@prisma/prisma-schema-wasm/-/prisma-schema-wasm-7.1.1-3.c2990dca591cba766e3b7ef5d9e8a84796e47ab7.tgz",
       "integrity": "sha512-/5JrsJQAOIWSl+9WMM/0ugd737kT9zdMNr7EFaP7ogeMxAhxQ78uaOV6JYGEocD8LC0gZx7MXmVE/CTfYdJ2iA==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@prisma/schema-engine-wasm": {
       "version": "7.1.1-3.c2990dca591cba766e3b7ef5d9e8a84796e47ab7",
       "resolved": "https://registry.npmjs.org/@prisma/schema-engine-wasm/-/schema-engine-wasm-7.1.1-3.c2990dca591cba766e3b7ef5d9e8a84796e47ab7.tgz",
       "integrity": "sha512-mXtzeePkSdqpr/HAIclqzQEf+tBzLawy7NQ9AaRCfg8N/cruavpsocgbSwOOfV7JTk9JubyzKuR3tp2bNNuWbQ==",
-      "dev": true,
       "license": "Apache-2.0"
     },
     "node_modules/@prisma/schema-files-loader": {
       "version": "6.19.3",
       "resolved": "https://registry.npmjs.org/@prisma/schema-files-loader/-/schema-files-loader-6.19.3.tgz",
       "integrity": "sha512-rnoL2PgopghakRZLCZwj+d7LPvjbY9mFholFWuibEKzwO7aqS16s60Hz4wxAnKwqOcS/M6pV7QLrsHBYnNR0KA==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@prisma/prisma-schema-wasm": "7.1.1-3.c2990dca591cba766e3b7ef5d9e8a84796e47ab7",
@@ -16287,7 +16274,6 @@
       "version": "10.5.0",
       "resolved": "https://registry.npmjs.org/chevrotain/-/chevrotain-10.5.0.tgz",
       "integrity": "sha512-Pkv5rBY3+CsHOYfV5g/Vs5JY9WTHHDEKOlohI2XeygaZhUeqhAlldZ8Hz9cRmxu709bvS08YzxHdTPHhffc13A==",
-      "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
         "@chevrotain/cst-dts-gen": "10.5.0",
@@ -16639,7 +16625,6 @@
       "version": "13.0.3",
       "resolved": "https://registry.npmjs.org/code-block-writer/-/code-block-writer-13.0.3.tgz",
       "integrity": "sha512-Oofo0pq3IKnsFtuHqSF7TqBfr71aeyZDVJ0HpmqB7FBM2qEigL0iPONSCZSO9pE9dZTAxANe5XHG9Uy0YMv8cg==",
-      "dev": true,
       "license": "MIT"
     },
     "node_modules/collapse-white-space": {
@@ -19886,7 +19871,6 @@
       "version": "11.3.0",
       "resolved": "https://registry.npmjs.org/fs-extra/-/fs-extra-11.3.0.tgz",
       "integrity": "sha512-Z4XaCL6dUDHfP/jT25jJKMmtxvuwbkrD1vNSMFlo9lNLY2c5FHYSQgHPRZUjAB26TpDEoW9HCOgplrdbaPV/ew==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "graceful-fs": "^4.2.0",
@@ -22553,7 +22537,6 @@
       "version": "2.1.0",
       "resolved": "https://registry.npmjs.org/lilconfig/-/lilconfig-2.1.0.tgz",
       "integrity": "sha512-utWOt/GHzuUxnLKxB6dk81RoOeoNeHgbrXiuGk4yyF5qlRz+iIVWu56E2fqGHFrXz0QNUhLB/8nKqvRH66JKGQ==",
-      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">=10"
@@ -26400,7 +26383,6 @@
       "version": "3.6.2",
       "resolved": "https://registry.npmjs.org/prisma-json-types-generator/-/prisma-json-types-generator-3.6.2.tgz",
       "integrity": "sha512-WX/oENQ0S74r/Wgd2uuHT5i3KbnwLFCP2Fq5ISzrXkus/htOC4uCaQPYuGP2m/wSeKZZCw1RxptTlD+ib7Ht/A==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "@prisma/generator-helper": "^6.16.1",
@@ -26426,7 +26408,6 @@
       "version": "2.3.0",
       "resolved": "https://registry.npmjs.org/prisma-kysely/-/prisma-kysely-2.3.0.tgz",
       "integrity": "sha512-/+VF2t2DlY+t/27hhyH5ULWxBAAsMBPgOo8Ltq7uXpBz49lUf4XuO1ff9HV0l7J3aDojG+YyczEvY0og9uRqsw==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "@mrleebo/prisma-ast": "^0.13.1",
@@ -27627,7 +27608,6 @@
       "version": "0.5.0",
       "resolved": "https://registry.npmjs.org/regexp-to-ast/-/regexp-to-ast-0.5.0.tgz",
       "integrity": "sha512-tlbJqcMHnPKI9zSrystikWKwHkBqu2a/Sgw01h3zFjvYrMxEDYHzzoMZnUrbIfpTFEsoRnnviOXNCzFiSc54Qw==",
-      "dev": true,
       "license": "MIT"
     },
     "node_modules/rehype-raw": {
@@ -31674,7 +31654,6 @@
       "version": "3.3.5",
       "resolved": "https://registry.npmjs.org/zod-prisma-types/-/zod-prisma-types-3.3.5.tgz",
       "integrity": "sha512-PDuRRCdX1d6ch6UclNvrqM1SLb2qvuaQPvZT/OHRrcxOQqQUnCz009aBc1uxuwMho1+d42TTDCQr+HPXhTSJtQ==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "@prisma/dmmf": "^6.16.3",
@@ -32431,17 +32410,17 @@
         "nanoid": "^5.1.6",
         "prisma": "^6.19.0",
         "prisma-extension-kysely": "^3.0.0",
+        "prisma-json-types-generator": "^3.6.2",
+        "prisma-kysely": "^2.3.0",
         "ts-pattern": "^5.9.0",
-        "zod": "^3.25.76"
+        "zod": "^3.25.76",
+        "zod-prisma-types": "3.3.5"
       },
       "devDependencies": {
         "dotenv": "^17.2.3",
         "dotenv-cli": "^11.0.0",
-        "prisma-json-types-generator": "^3.6.2",
-        "prisma-kysely": "^2.3.0",
         "tsx": "^4.23.1",
-        "typescript": "5.6.2",
-        "zod-prisma-types": "3.3.5"
+        "typescript": "5.6.2"
       }
     },
     "packages/prisma/node_modules/@esbuild/aix-ppc64": {

package.json

@@ -5,7 +5,7 @@
     "apps/*",
     "packages/*"
   ],
-  "version": "2.18.0",
+  "version": "2.17.0",
   "scripts": {
     "postinstall": "patch-package",
     "build": "turbo run build",
@@ -41,10 +41,10 @@
     "translate:extract": "lingui extract --clean",
     "translate:compile": "lingui compile"
   },
-  "packageManager": "npm@11.19.1",
+  "packageManager": "npm@11.11.0",
   "engines": {
-    "npm": ">=11.17.0",
-    "node": ">=24.0.0"
+    "npm": ">=11.11.0",
+    "node": ">=22.0.0"
   },
   "devDependencies": {
     "@biomejs/biome": "2.4.8",

packages/app-tests/e2e/admin/global-search.spec.ts

@@ -10,7 +10,7 @@ test.describe.configure({ mode: 'parallel' });
 
 const nanoid = customAlphabet('1234567890abcdef', 10);
 
-const ADMIN_PROMPT_PLACEHOLDER = 'Search documents, users, organizations…';
+const ADMIN_PROMPT_PLACEHOLDER = 'Search documents, users, organisations…';
 
 test('[ADMIN][GLOBAL_SEARCH]: numeric query shows verified user result and navigates', async ({ page }) => {
   const { user: adminUser } = await seedUser({ isAdmin: true });

packages/app-tests/e2e/admin/organisations/delete-organisation.spec.ts

@@ -411,7 +411,7 @@ test('[ADMIN][DELETE_ORG]: the original owner loses access after deletion', asyn
   });
 
   // They should NOT see the organisation settings heading for this org.
-  await expect(page.getByText('Organization Settings')).not.toBeVisible();
+  await expect(page.getByText('Organisation Settings')).not.toBeVisible();
 });
 
 // ─── Access control: UI ──────────────────────────────────────────────────────

packages/app-tests/e2e/admin/organisations/update-organisation-member-role.spec.ts

@@ -50,9 +50,9 @@ test('[ADMIN]: promote member to owner', async ({ page }) => {
   });
 
   // Verify we're on the admin organisation page
-  await expect(page.getByText(`Manage organization`)).toBeVisible();
+  await expect(page.getByText(`Manage organisation`)).toBeVisible();
 
-  await expect(page.getByLabel('Organization Name')).toHaveValue(organisation.name);
+  await expect(page.getByLabel('Organisation Name')).toHaveValue(organisation.name);
 
   // Check that the organisation members table shows the correct roles
   const ownerRow = page.getByRole('row', { name: ownerUser.email });
@@ -356,7 +356,7 @@ test('[ADMIN]: error handling for invalid organisation', async ({ page }) => {
   });
 
   // Should show 404 error
-  await expect(page.getByRole('heading', { name: 'Organization not found' })).toBeVisible({
+  await expect(page.getByRole('heading', { name: 'Organisation not found' })).toBeVisible({
     timeout: 10_000,
   });
 });
@@ -525,8 +525,8 @@ test('[ADMIN]: verify organisation access after ownership change', async ({ page
 
   // Should be able to access organisation settings
   await expect(page.getByTestId('unified-settings-sidebar')).toBeVisible();
-  await expect(page.getByLabel('Organization Name*')).toBeVisible();
-  await expect(page.getByLabel('Organization Name*')).toBeEnabled();
+  await expect(page.getByLabel('Organisation Name*')).toBeVisible();
+  await expect(page.getByLabel('Organisation Name*')).toBeEnabled();
 
   // Should have delete permissions
   await expect(page.getByRole('button', { name: 'Delete' })).toBeVisible();

packages/app-tests/e2e/documents/bulk-document-actions.spec.ts

@@ -408,7 +408,7 @@ test('[BULK_ACTIONS]: can cancel multiple pending documents', async ({ page }) =
 
   await dialog.getByRole('button', { name: 'Cancel documents' }).click();
 
-  await expectToastTextToBeVisible(page, 'Documents canceled');
+  await expectToastTextToBeVisible(page, 'Documents cancelled');
 
   // Selection clears after a successful cancel.
   await expect(page.getByText(/\d+ selected/)).not.toBeVisible();
@@ -455,7 +455,7 @@ test('[BULK_ACTIONS]: bulk cancel only affects pending documents', async ({ page
   await dialog.getByRole('button', { name: 'Cancel documents' }).click();
 
   // Only one of the three was pending, so this is a partial result.
-  await expectToastTextToBeVisible(page, 'Documents partially canceled');
+  await expectToastTextToBeVisible(page, 'Documents partially cancelled');
 
   const pendingEnvelope = await prisma.envelope.findFirstOrThrow({
     where: { id: pending.id },
@@ -505,7 +505,7 @@ test('[BULK_ACTIONS]: a MEMBER cannot bulk cancel documents they do not own', as
 
   // The server rejects the cancellation for a document the MEMBER does not own,
   // so it reports zero cancelled (a partial result with the document in failedIds).
-  await expectToastTextToBeVisible(page, 'Documents partially canceled');
+  await expectToastTextToBeVisible(page, 'Documents partially cancelled');
 
   // The document remains pending.
   const envelope = await prisma.envelope.findFirstOrThrow({

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

@@ -41,7 +41,7 @@ const cancelDocumentViaUi = async (page: Page, documentTitle: string, reason?: s
   await expect(page.getByRole('heading', { name: 'Are you sure?' })).toBeVisible();
 
   if (reason) {
-    await page.getByPlaceholder('Add an optional reason for canceling this document').fill(reason);
+    await page.getByPlaceholder('Add an optional reason for cancelling this document').fill(reason);
   }
 
   await page.getByRole('button', { name: 'Cancel document' }).click();
@@ -58,13 +58,13 @@ test('[DOCUMENTS]: cancelling a pending document keeps it in the owner dashboard
 
   await cancelDocumentViaUi(page, 'Document 1 - Pending', 'No longer required');
 
-  await expectToastTextToBeVisible(page, 'Document canceled');
+  await expectToastTextToBeVisible(page, 'Document cancelled');
 
   // The document must remain in the dashboard, unlike deleting a pending document.
   await checkDocumentCounts(page, { inbox: 0, pending: 0, cancelled: 1, all: 1 });
 
   // The cancelled document is still listed.
-  await selectDocumentStatusFilter(page, 'Canceled');
+  await selectDocumentStatusFilter(page, 'Cancelled');
   await expect(page.getByRole('link', { name: 'Document 1 - Pending' })).toBeVisible();
 
   // The envelope status is persisted as CANCELLED.
@@ -95,7 +95,7 @@ test('[DOCUMENTS]: cancelling a pending document retains it for recipients', asy
 
   await cancelDocumentViaUi(page, 'Document 1 - Pending');
 
-  await expectToastTextToBeVisible(page, 'Document canceled');
+  await expectToastTextToBeVisible(page, 'Document cancelled');
 
   await apiSignout({ page });
 
@@ -125,10 +125,10 @@ test('[DOCUMENTS]: a cancelled document can be deleted, hiding it from the owner
   });
 
   await cancelDocumentViaUi(page, 'Document 1 - Pending');
-  await expectToastTextToBeVisible(page, 'Document canceled');
+  await expectToastTextToBeVisible(page, 'Document cancelled');
 
   // Delete the now-cancelled document. Being terminal, it should soft delete (hide).
-  await selectDocumentStatusFilter(page, 'Canceled');
+  await selectDocumentStatusFilter(page, 'Cancelled');
 
   const documentActionBtn = page
     .locator('tr', { hasText: 'Document 1 - Pending' })
@@ -328,7 +328,7 @@ test('[DOCUMENTS]: a team ADMIN sees and can use the Cancel action on a document
 
   await cancelDocumentViaUi(page, 'Admin Cancellable Document');
 
-  await expectToastTextToBeVisible(page, 'Document canceled');
+  await expectToastTextToBeVisible(page, 'Document cancelled');
 
   const envelope = await prisma.envelope.findFirstOrThrow({
     where: { id: document.id },

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

@@ -29,11 +29,11 @@ test('[ORGANISATIONS]: create and delete organisation', async ({ page }) => {
 
   await page.waitForURL(`/settings/organisations`);
   await expectTextToBeVisible(page, 'No results found');
-  await page.getByRole('button', { name: 'Create organization' }).click();
+  await page.getByRole('button', { name: 'Create organisation' }).click();
 
-  await page.getByLabel('Organization Name*').fill('test');
+  await page.getByLabel('Organisation Name*').fill('test');
   await page.getByRole('button', { name: 'Create' }).click();
-  await expect(page.getByText('Your organization has been created').first()).toBeVisible();
+  await expect(page.getByText('Your organisation has been created').first()).toBeVisible();
   await page.reload();
 
   await page.getByRole('row').filter({ hasText: 'test' }).getByRole('link').nth(1).click();
@@ -53,12 +53,12 @@ test('[ORGANISATIONS]: manage general settings', async ({ page }) => {
   const updatedOrganisationId = `organisation-${Date.now()}`;
 
   // Update team.
-  await page.getByLabel('Organization Name*').click();
-  await page.getByLabel('Organization Name*').clear();
-  await page.getByLabel('Organization Name*').fill(updatedOrganisationId);
-  await page.getByLabel('Organization URL*').click();
-  await page.getByLabel('Organization URL*').clear();
-  await page.getByLabel('Organization URL*').fill(updatedOrganisationId);
+  await page.getByLabel('Organisation Name*').click();
+  await page.getByLabel('Organisation Name*').clear();
+  await page.getByLabel('Organisation Name*').fill(updatedOrganisationId);
+  await page.getByLabel('Organisation URL*').click();
+  await page.getByLabel('Organisation URL*').clear();
+  await page.getByLabel('Organisation URL*').fill(updatedOrganisationId);
 
   await page.getByRole('button', { name: 'Save changes' }).click();
 
@@ -277,8 +277,8 @@ test('[ORGANISATIONS]: manage groups and members', async ({ page }) => {
   // Create a custom group A with 3 members "ORGANISATION ADMIN" to check that they get the correct roles.
   await page.getByRole('button', { name: 'Create group' }).click();
   await page.getByRole('textbox', { name: 'Group Name *' }).fill('CUSTOM_GROUP');
-  await page.getByRole('combobox').filter({ hasText: 'Organization Member' }).click();
-  await page.getByRole('option', { name: 'Organization Admin' }).click();
+  await page.getByRole('combobox').filter({ hasText: 'Organisation Member' }).click();
+  await page.getByRole('option', { name: 'Organisation Admin' }).click();
   await page.getByTestId('group-members-picker').click();
   await page.getByRole('option', { name: 'Member1' }).click();
   await page.getByRole('option', { name: 'Member2' }).click();
@@ -291,16 +291,16 @@ test('[ORGANISATIONS]: manage groups and members', async ({ page }) => {
   await page.goto(`/o/${organisation.url}/settings/members`);
 
   // Confirm org roles have been applied to these members.
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(memberEmail1)).toBeVisible();
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(memberEmail2)).toBeVisible();
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(memberEmail3)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(memberEmail1)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(memberEmail2)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(memberEmail3)).toBeVisible();
 
   // Test updating the group.
   await page.goto(`/o/${organisation.url}/settings/groups`);
   await page.getByRole('link', { name: 'Manage' }).click();
   await page.getByRole('textbox', { name: 'Group Name *' }).fill('CUSTOM_GROUP_A');
-  await page.getByRole('combobox').filter({ hasText: 'Organization Admin' }).click();
-  await page.getByRole('option', { name: 'Organization Member' }).click();
+  await page.getByRole('combobox').filter({ hasText: 'Organisation Admin' }).click();
+  await page.getByRole('option', { name: 'Organisation Member' }).click();
   // Remove Member3 by clicking the X on its chip in the multiselect.
   await page
     .getByTestId('group-members-picker')
@@ -327,16 +327,16 @@ test('[ORGANISATIONS]: manage groups and members', async ({ page }) => {
   await page.goto(`/o/${organisation.url}/settings/members`);
 
   // Confirm admins still get admin roles.
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(adminEmail1)).toBeVisible();
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(adminEmail2)).toBeVisible();
-  await expect(page.getByRole('row').filter({ hasText: 'Organization Admin' }).getByText(adminEmail3)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(adminEmail1)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(adminEmail2)).toBeVisible();
+  await expect(page.getByRole('row').filter({ hasText: 'Organisation Admin' }).getByText(adminEmail3)).toBeVisible();
 
   // Create another custom group with 3 members with "ORGANISATION MEMBER" role.
   await page.goto(`/o/${organisation.url}/settings/groups`);
   await page.getByRole('button', { name: 'Create group' }).click();
   await page.getByRole('textbox', { name: 'Group Name *' }).fill('CUSTOM_GROUP_B');
-  await page.getByRole('combobox').filter({ hasText: 'Organization Member' }).click();
-  await page.getByRole('option', { name: 'Organization Admin' }).click();
+  await page.getByRole('combobox').filter({ hasText: 'Organisation Member' }).click();
+  await page.getByRole('option', { name: 'Organisation Admin' }).click();
   await page.getByTestId('group-members-picker').click();
   await page.getByRole('option', { name: 'Member4' }).click();
   await page.getByRole('option', { name: 'Member5' }).click();
@@ -537,6 +537,6 @@ test('[ORGANISATIONS]: leave organisation', async ({ page }) => {
   await page.getByRole('button', { name: 'Leave' }).click();
   await page.getByRole('button', { name: 'Leave' }).click();
 
-  await expect(page.getByText('You have successfully left this organization').first()).toBeVisible();
+  await expect(page.getByText('You have successfully left this organisation').first()).toBeVisible();
   await expect(page.getByText('No results found').first()).toBeVisible();
 });

packages/app-tests/e2e/organisations/organisation-quota-banner.spec.ts

@@ -7,8 +7,8 @@ import { expect, test } from '@playwright/test';
 
 import { apiSignin } from '../fixtures/authentication';
 
-const BANNER_EXCEEDED_TEXT = 'Your organization has exceeded a fair use limit';
-const BANNER_NEARING_TEXT = 'Your organization is approaching a fair use limit';
+const BANNER_EXCEEDED_TEXT = 'Your organisation has exceeded a fair use limit';
+const BANNER_NEARING_TEXT = 'Your organisation is approaching a fair use limit';
 
 type SeedQuotaStateOptions = {
   organisationId: string;
@@ -162,7 +162,7 @@ test('[QUOTA BANNER]: is hidden for free-claim organisations', async ({ page })
   });
 
   // Anchor on a stable element so banner-absence is meaningful (page fully loaded).
-  await expect(page.getByLabel('Organization Name*')).toBeVisible();
+  await expect(page.getByLabel('Organisation Name*')).toBeVisible();
 
   await expect(page.getByText(BANNER_EXCEEDED_TEXT)).toBeHidden();
   await expect(page.getByRole('button', { name: 'Learn more' })).toBeHidden();

packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts

@@ -176,7 +176,7 @@ test('[ORGANISATIONS]: manage branding preferences', async ({ page }) => {
 
   // Test inheritance by setting team back to inherit from organisation
   await page.getByTestId('enable-branding').click();
-  await page.getByRole('option', { name: 'Inherit from organization' }).click();
+  await page.getByRole('option', { name: 'Inherit from organisation' }).click();
   await page.getByRole('button', { name: 'Save changes' }).first().click();
   await expect(page.getByText('Your branding preferences have been updated').first()).toBeVisible();
 
@@ -254,9 +254,9 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
   await page
     .getByTestId('inheritable-email-document-settings')
     .getByRole('combobox')
-    .filter({ hasText: 'Inherit from organization' })
+    .filter({ hasText: 'Inherit from organisation' })
     .click();
-  await page.getByRole('option', { name: 'Override organization settings' }).click();
+  await page.getByRole('option', { name: 'Override organisation settings' }).click();
 
   // Update some email settings
   await page.getByRole('checkbox', { name: 'Email recipients with a signing request' }).uncheck();
@@ -308,8 +308,8 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
 
   // Test inheritance by setting team back to inherit from organisation
   await page.getByRole('textbox', { name: 'Reply to email' }).fill('');
-  await page.getByRole('combobox').filter({ hasText: 'Override organization settings' }).click();
-  await page.getByRole('option', { name: 'Inherit from organization' }).click();
+  await page.getByRole('combobox').filter({ hasText: 'Override organisation settings' }).click();
+  await page.getByRole('option', { name: 'Inherit from organisation' }).click();
   await page.getByRole('button', { name: 'Save changes' }).first().click();
   await expect(page.getByText('Your email preferences have been updated').first()).toBeVisible();
 

packages/app-tests/e2e/settings/unified-settings.spec.ts

@@ -248,7 +248,7 @@ test.describe('Unified Settings', () => {
 
     // Wait for the organisation page to actually render — asserting straight after
     // `waitForURL` can read the previous scope's still-mounted sidebar and pass falsely.
-    await expect(page.getByTestId('settings-scope-breadcrumb-chip')).toContainText('Organization Settings');
+    await expect(page.getByTestId('settings-scope-breadcrumb-chip')).toContainText('Organisation Settings');
 
     await expect(trigger).toContainText(selected.name);
 
@@ -283,7 +283,7 @@ test.describe('Unified Settings', () => {
 
     // Selecting the inherit option stages the field back to inherited.
     await page.getByTestId('document-language-trigger').click();
-    await page.getByRole('option', { name: /inherit from organization/i }).click();
+    await page.getByRole('option', { name: /inherit from organisation/i }).click();
 
     await expect(langStatus).toHaveText(/inherited/i);
   });
@@ -450,7 +450,7 @@ test.describe('Unified Settings', () => {
     // An empty group would just look broken, so it explains itself directly under the switcher.
     const emptyState = sidebar.getByTestId('unified-settings-organisation-empty-state');
     await expect(emptyState).toBeVisible();
-    await expect(emptyState).toContainText(/permission to manage this organization/i);
+    await expect(emptyState).toContainText(/permission to manage this organisation/i);
 
     // Team and account pages remain navigable.
     await expect(sidebar.getByTestId('unified-settings-nav-team-general')).toBeVisible();

packages/lib/constants/app.ts

@@ -93,8 +93,6 @@ export const NEXT_PRIVATE_USE_PLAYWRIGHT_PDF = () => env('NEXT_PRIVATE_USE_PLAYW
 
 export const NEXT_PRIVATE_SIGNING_TIMESTAMP_AUTHORITY = () => env('NEXT_PRIVATE_SIGNING_TIMESTAMP_AUTHORITY');
 
-export const NEXT_PRIVATE_SIGNING_TRANSPORT = () => env('NEXT_PRIVATE_SIGNING_TRANSPORT') || 'local';
-
 /**
  * Whether this Documenso instance is running in CSC (Cloud Signature Consortium) mode.
  *

packages/lib/jobs/definitions/internal/bulk-send-template.handler.ts

@@ -2,10 +2,12 @@ import { BulkSendCompleteEmail } from '@documenso/email/templates/bulk-send-comp
 import { sendDocument } from '@documenso/lib/server-only/document/send-document';
 import { createDocumentFromTemplate } from '@documenso/lib/server-only/template/create-document-from-template';
 import { getTemplateById } from '@documenso/lib/server-only/template/get-template-by-id';
-import { validateBulkSendCsv } from '@documenso/lib/server-only/template/validate-bulk-send-csv';
+import { zEmail } from '@documenso/lib/utils/zod';
 import { prisma } from '@documenso/prisma';
 import { msg } from '@lingui/macro';
+import { parse } from 'csv-parse/sync';
 import { createElement } from 'react';
+import { z } from 'zod';
 
 import { getI18nInstance } from '../../../client-only/providers/i18n-server';
 import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
@@ -15,6 +17,14 @@ import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
 import type { JobRunIO } from '../../client/_internal/job';
 import type { TBulkSendTemplateJobDefinition } from './bulk-send-template';
 
+const ZRecipientRowSchema = z.object({
+  name: z.string().optional(),
+  email: z.union([
+    zEmail('Value must be a valid email or empty string'),
+    z.string().max(0, { message: 'Value must be a valid email or empty string' }),
+  ]),
+});
+
 export const run = async ({ payload, io }: { payload: TBulkSendTemplateJobDefinition; io: JobRunIO }) => {
   const { userId, teamId, templateId, csvContent, sendImmediately, requestMetadata } = payload;
 
@@ -31,20 +41,24 @@ export const run = async ({ payload, io }: { payload: TBulkSendTemplateJobDefini
     throw new Error('Template not found');
   }
 
-  const { recipients } = template;
+  // eslint-disable-next-line @typescript-eslint/no-explicit-any
+  const rows = parse<any>(csvContent, { columns: true, skip_empty_lines: true });
 
-  // The CSV is validated upfront when the bulk send is uploaded, this acts as
-  // a final safeguard prior to processing.
-  const csvValidationResult = validateBulkSendCsv({
-    csvContent,
-    recipientCount: recipients.length,
-  });
-
-  if (!csvValidationResult.success) {
-    throw new Error(`Bulk send CSV failed validation: ${JSON.stringify(csvValidationResult.error)}`);
+  if (rows.length > 100) {
+    throw new Error('Maximum 100 rows allowed per upload');
   }
 
-  const rows = csvValidationResult.data;
+  const { recipients } = template;
+
+  // Validate CSV structure
+  const csvHeaders = Object.keys(rows[0]);
+  const requiredHeaders = recipients.map((_, index) => `recipient_${index + 1}_email`);
+
+  for (const header of requiredHeaders) {
+    if (!csvHeaders.includes(header)) {
+      throw new Error(`Missing required column: ${header}`);
+    }
+  }
 
   const user = await prisma.user.findFirstOrThrow({
     where: {
@@ -65,6 +79,22 @@ export const run = async ({ payload, io }: { payload: TBulkSendTemplateJobDefini
   // Process each row
   for (const [rowIndex, row] of rows.entries()) {
     try {
+      for (const [recipientIndex] of recipients.entries()) {
+        const nameKey = `recipient_${recipientIndex + 1}_name`;
+        const emailKey = `recipient_${recipientIndex + 1}_email`;
+
+        const parsed = ZRecipientRowSchema.safeParse({
+          name: row[nameKey],
+          email: row[emailKey],
+        });
+
+        if (!parsed.success) {
+          throw new Error(
+            `Invalid recipient data provided for ${emailKey}, ${nameKey}: ${parsed.error.issues?.[0]?.message}`,
+          );
+        }
+      }
+
       const envelope = await io.runTask(`create-document-${rowIndex}`, async () => {
         return await createDocumentFromTemplate({
           id: {

packages/lib/server-only/cert/cert-status.ts

@@ -1,36 +1,26 @@
-import { X509Certificate } from 'node:crypto';
+import * as fs from 'node:fs';
 
-import { createLocalSigner } from '@documenso/signing/transports/local';
+import { env } from '@documenso/lib/utils/env';
 
-import { NEXT_PRIVATE_SIGNING_TRANSPORT } from '../../constants/app';
-
-/**
- * Whether the local P12 opens with the configured passphrase and is in date.
- * Skips AIA so this stays offline. gcloud-hsm and csc always report available.
- */
-export const getCertificateStatus = async () => {
-  const transport = NEXT_PRIVATE_SIGNING_TRANSPORT();
-
-  // Cannot inspect a remote HSM or CSC provider from this process.
-  if (transport === 'gcloud-hsm' || transport === 'csc') {
+export const getCertificateStatus = () => {
+  if (env('NEXT_PRIVATE_SIGNING_TRANSPORT') !== 'local') {
     return { isAvailable: true };
   }
 
-  // Anything else (typo, leftover `http`) would throw at seal time.
-  if (transport !== 'local') {
-    return { isAvailable: false };
+  if (env('NEXT_PRIVATE_SIGNING_LOCAL_FILE_CONTENTS')) {
+    return { isAvailable: true };
   }
 
+  const defaultPath = env('NODE_ENV') === 'production' ? '/opt/documenso/cert.p12' : './example/cert.p12';
+
+  const filePath = env('NEXT_PRIVATE_SIGNING_LOCAL_FILE_PATH') || defaultPath;
+
   try {
-    const signer = await createLocalSigner({ buildChain: false });
+    fs.accessSync(filePath, fs.constants.F_OK | fs.constants.R_OK);
 
-    const certificate = new X509Certificate(Buffer.from(signer.certificate));
+    const stats = fs.statSync(filePath);
 
-    const now = new Date();
-
-    const isWithinValidityPeriod = new Date(certificate.validFrom) <= now && now <= new Date(certificate.validTo);
-
-    return { isAvailable: isWithinValidityPeriod };
+    return { isAvailable: stats.size > 0 };
   } catch {
     return { isAvailable: false };
   }

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/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/lib/server-only/template/validate-bulk-send-csv.test.ts

@@ -1,208 +0,0 @@
-import { describe, expect, it } from 'vitest';
-
-import type { TBulkSendCsvError, TValidateBulkSendCsvResult } from './validate-bulk-send-csv';
-import { validateBulkSendCsv } from './validate-bulk-send-csv';
-
-const buildCsv = (headers: string[], rows: string[][]) =>
-  [headers.join(','), ...rows.map((row) => row.join(','))].join('\n');
-
-const expectFailure = (result: TValidateBulkSendCsvResult): TBulkSendCsvError => {
-  if (result.success) {
-    throw new Error('Expected validation to fail, but it passed');
-  }
-
-  return result.error;
-};
-
-describe('validateBulkSendCsv', () => {
-  describe('valid CSVs', () => {
-    it('returns the parsed rows for a valid CSV', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email', 'recipient_1_name'],
-        [
-          ['alice@example.com', 'Alice'],
-          ['bob@example.com', 'Bob'],
-        ],
-      );
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 1 });
-
-      expect(result).toEqual({
-        success: true,
-        data: [
-          { recipient_1_email: 'alice@example.com', recipient_1_name: 'Alice' },
-          { recipient_1_email: 'bob@example.com', recipient_1_name: 'Bob' },
-        ],
-      });
-    });
-
-    it('allows an empty string email so template defaults can be used', () => {
-      const csvContent = buildCsv(['recipient_1_email', 'recipient_1_name'], [['', 'Alice']]);
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 1 });
-
-      expect(result.success).toBe(true);
-    });
-
-    it('allows the optional name column to be omitted entirely', () => {
-      const csvContent = buildCsv(['recipient_1_email'], [['alice@example.com']]);
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 1 });
-
-      expect(result.success).toBe(true);
-    });
-
-    it('allows unknown extra columns', () => {
-      const csvContent = buildCsv(['recipient_1_email', 'unrelated_column'], [['alice@example.com', 'anything']]);
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 1 });
-
-      expect(result.success).toBe(true);
-    });
-
-    it('validates columns for every configured recipient', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email', 'recipient_2_email'],
-        [['alice@example.com', 'bob@example.com']],
-      );
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 2 });
-
-      expect(result.success).toBe(true);
-    });
-
-    it('allows exactly the maximum number of rows', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email'],
-        Array.from({ length: 100 }, (_, index) => [`user${index}@example.com`]),
-      );
-
-      const result = validateBulkSendCsv({ csvContent, recipientCount: 1 });
-
-      expect(result.success).toBe(true);
-    });
-  });
-
-  describe('PARSE_ERROR', () => {
-    it('rejects a CSV that cannot be parsed', () => {
-      const csvContent = 'recipient_1_email\n"unclosed quote';
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'PARSE_ERROR' });
-    });
-
-    it('rejects a CSV with inconsistent column counts', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email', 'recipient_1_name'],
-        [['alice@example.com', 'Alice', 'unexpected-extra-value']],
-      );
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'PARSE_ERROR' });
-    });
-  });
-
-  describe('EMPTY', () => {
-    it('rejects an empty file', () => {
-      const error = expectFailure(validateBulkSendCsv({ csvContent: '', recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'EMPTY' });
-    });
-
-    it('rejects a CSV containing only a header row', () => {
-      const csvContent = buildCsv(['recipient_1_email', 'recipient_1_name'], []);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'EMPTY' });
-    });
-  });
-
-  describe('ROW_LIMIT_EXCEEDED', () => {
-    it('rejects a CSV exceeding the default limit of 100 rows', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email'],
-        Array.from({ length: 101 }, (_, index) => [`user${index}@example.com`]),
-      );
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'ROW_LIMIT_EXCEEDED', rowCount: 101, maxRows: 100 });
-    });
-
-    it('respects a custom maxRows option', () => {
-      const csvContent = buildCsv(['recipient_1_email'], [['alice@example.com'], ['bob@example.com']]);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1, maxRows: 1 }));
-
-      expect(error).toEqual({ type: 'ROW_LIMIT_EXCEEDED', rowCount: 2, maxRows: 1 });
-    });
-  });
-
-  describe('MISSING_COLUMNS', () => {
-    it('rejects a CSV missing a required email column', () => {
-      const csvContent = buildCsv(['recipient_1_name'], [['Alice']]);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toEqual({ type: 'MISSING_COLUMNS', missingColumns: ['recipient_1_email'] });
-    });
-
-    it('reports every missing column', () => {
-      const csvContent = buildCsv(['recipient_1_email'], [['alice@example.com']]);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 3 }));
-
-      expect(error).toEqual({
-        type: 'MISSING_COLUMNS',
-        missingColumns: ['recipient_2_email', 'recipient_3_email'],
-      });
-    });
-  });
-
-  describe('INVALID_RECIPIENTS', () => {
-    it('rejects a CSV containing an invalid email', () => {
-      const csvContent = buildCsv(['recipient_1_email'], [['not-an-email']]);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toMatchObject({
-        type: 'INVALID_RECIPIENTS',
-        rowErrors: [{ row: 1, column: 'recipient_1_email' }],
-      });
-    });
-
-    it('references the offending row and column', () => {
-      const csvContent = buildCsv(['recipient_1_email'], [['alice@example.com'], ['not-an-email']]);
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 1 }));
-
-      expect(error).toMatchObject({
-        type: 'INVALID_RECIPIENTS',
-        rowErrors: [{ row: 2, column: 'recipient_1_email' }],
-      });
-    });
-
-    it('aggregates errors across multiple rows and recipients', () => {
-      const csvContent = buildCsv(
-        ['recipient_1_email', 'recipient_2_email'],
-        [
-          ['not-an-email', 'bob@example.com'],
-          ['alice@example.com', 'also-not-an-email'],
-        ],
-      );
-
-      const error = expectFailure(validateBulkSendCsv({ csvContent, recipientCount: 2 }));
-
-      expect(error).toMatchObject({
-        type: 'INVALID_RECIPIENTS',
-        rowErrors: [
-          { row: 1, column: 'recipient_1_email' },
-          { row: 2, column: 'recipient_2_email' },
-        ],
-      });
-    });
-  });
-});

packages/lib/server-only/template/validate-bulk-send-csv.ts

@@ -1,117 +0,0 @@
-import { parse } from 'csv-parse/sync';
-import { z } from 'zod';
-
-import { zEmail } from '../../utils/zod';
-
-const ZRecipientRowSchema = z.object({
-  name: z.string().optional(),
-  email: z.union([
-    zEmail('Value must be a valid email or empty string'),
-    z.string().max(0, { message: 'Value must be a valid email or empty string' }),
-  ]),
-});
-
-export type TBulkSendCsvRow = Record<string, string | undefined>;
-
-export type TBulkSendCsvRowError = {
-  /**
-   * The 1-indexed row number the error occurred on, excluding the header row.
-   */
-  row: number;
-
-  /**
-   * The column the error occurred in, such as `recipient_1_email`.
-   */
-  column: string;
-
-  message: string;
-};
-
-export type TBulkSendCsvError =
-  | { type: 'PARSE_ERROR' }
-  | { type: 'EMPTY' }
-  | { type: 'ROW_LIMIT_EXCEEDED'; rowCount: number; maxRows: number }
-  | { type: 'MISSING_COLUMNS'; missingColumns: string[] }
-  | { type: 'INVALID_RECIPIENTS'; rowErrors: TBulkSendCsvRowError[] };
-
-export type TValidateBulkSendCsvResult =
-  | { success: true; data: TBulkSendCsvRow[] }
-  | { success: false; error: TBulkSendCsvError };
-
-export type ValidateBulkSendCsvOptions = {
-  csvContent: string;
-
-  /**
-   * The number of recipients configured on the template, used to derive the
-   * required `recipient_N_email` columns.
-   */
-  recipientCount: number;
-
-  maxRows?: number;
-};
-
-/**
- * Validate the CSV provided for a template bulk send.
- *
- * Returns a discriminated union so callers can surface structured error
- * details, such as which rows contain invalid recipients.
- */
-export const validateBulkSendCsv = ({
-  csvContent,
-  recipientCount,
-  maxRows = 100,
-}: ValidateBulkSendCsvOptions): TValidateBulkSendCsvResult => {
-  let rows: TBulkSendCsvRow[];
-
-  try {
-    rows = parse(csvContent, { columns: true, skip_empty_lines: true });
-  } catch {
-    return { success: false, error: { type: 'PARSE_ERROR' } };
-  }
-
-  if (rows.length === 0) {
-    return { success: false, error: { type: 'EMPTY' } };
-  }
-
-  if (rows.length > maxRows) {
-    return { success: false, error: { type: 'ROW_LIMIT_EXCEEDED', rowCount: rows.length, maxRows } };
-  }
-
-  const csvHeaders = Object.keys(rows[0]);
-
-  const requiredHeaders = Array.from({ length: recipientCount }, (_, index) => `recipient_${index + 1}_email`);
-
-  const missingColumns = requiredHeaders.filter((header) => !csvHeaders.includes(header));
-
-  if (missingColumns.length > 0) {
-    return { success: false, error: { type: 'MISSING_COLUMNS', missingColumns } };
-  }
-
-  const rowErrors: TBulkSendCsvRowError[] = [];
-
-  for (const [rowIndex, row] of rows.entries()) {
-    for (let recipientIndex = 0; recipientIndex < recipientCount; recipientIndex += 1) {
-      const nameKey = `recipient_${recipientIndex + 1}_name`;
-      const emailKey = `recipient_${recipientIndex + 1}_email`;
-
-      const parsed = ZRecipientRowSchema.safeParse({
-        name: row[nameKey],
-        email: row[emailKey],
-      });
-
-      if (!parsed.success) {
-        rowErrors.push({
-          row: rowIndex + 1,
-          column: emailKey,
-          message: parsed.error.issues?.[0]?.message ?? 'Invalid value',
-        });
-      }
-    }
-  }
-
-  if (rowErrors.length > 0) {
-    return { success: false, error: { type: 'INVALID_RECIPIENTS', rowErrors } };
-  }
-
-  return { success: true, data: rows };
-};

packages/lib/server-only/user/create-user.ts

@@ -35,6 +35,33 @@ export const createUser = async ({ name, email, password, signature }: CreateUse
     },
   });
 
+  // Todo: (RR7) Migrate to use this after RR7.
+  // Note: If we actually ever proceed with this, there are multiple
+  // locations where we will need to update this.
+  // const user = await prisma.$transaction(async (tx) => {
+  //   const user = await tx.user.create({
+  //     data: {
+  //       name,
+  //       email: email.toLowerCase(),
+  //       password: hashedPassword, // Todo: (RR7) Drop password.
+  //       signature,
+  //     },
+  //   });
+
+  //   await tx.account.create({
+  //     data: {
+  //       userId: user.id,
+  //       type: 'emailPassword', // Todo: (RR7)
+  //       provider: 'DOCUMENSO', // Todo: (RR7) Enums
+  //       providerAccountId: user.id.toString(),
+  //       password: hashedPassword,
+  //     },
+  //   });
+
+  //   return user;
+  // });
+
+  // Not used at the moment, uncomment if required.
   await onCreateUserHook(user).catch((err) => {
     // Todo: (RR7) Add logging.
     console.error(err);

packages/lib/server-only/webhooks/is-private-url.test.ts

@@ -81,20 +81,13 @@ describe('isPrivateUrl', () => {
       expect(isPrivateUrl('http://[fd12::1]')).toBe(true);
     });
 
-    it('should detect private IPv4-mapped IPv6 addresses (URL parser normalizes to hex)', () => {
-      // new URL() normalizes "::ffff:127.0.0.1" to the hex form "::ffff:7f00:1",
-      // so the embedded IPv4 must be decoded and re-checked. Otherwise a literal
-      // host such as http://[::ffff:127.0.0.1] bypasses every dotted-decimal
-      // check above (SSRF, see #2901).
-      expect(isPrivateUrl('http://[::ffff:127.0.0.1]')).toBe(true);
-      expect(isPrivateUrl('http://[::ffff:10.0.0.1]')).toBe(true);
-      expect(isPrivateUrl('http://[::ffff:192.168.0.1]')).toBe(true);
-      expect(isPrivateUrl('http://[::ffff:169.254.169.254]')).toBe(true);
-    });
-
-    it('should still allow public IPv4-mapped IPv6 addresses', () => {
+    it('should not catch IPv4-mapped IPv6 in URL form (URL parser normalizes to hex)', () => {
+      // new URL() normalizes "::ffff:127.0.0.1" to "::ffff:7f00:1" which none
+      // of the checks handle. This is fine because dns.lookup never returns
+      // IPv4-mapped addresses — it returns plain IPv4 (family: 4) instead.
+      expect(isPrivateUrl('http://[::ffff:127.0.0.1]')).toBe(false);
+      expect(isPrivateUrl('http://[::ffff:10.0.0.1]')).toBe(false);
       expect(isPrivateUrl('http://[::ffff:8.8.8.8]')).toBe(false);
-      expect(isPrivateUrl('http://[::ffff:1.1.1.1]')).toBe(false);
     });
   });
 

packages/lib/server-only/webhooks/is-private-url.ts

@@ -69,25 +69,11 @@ export const isPrivateUrl = (url: string): boolean => {
       }
     }
 
-    // IPv4-mapped IPv6, dotted form (e.g. ::ffff:127.0.0.1)
-    const v4MappedDotted = normalizedHost.match(/^::ffff:(\d+\.\d+\.\d+\.\d+)$/i);
+    // IPv4-mapped IPv6 (e.g. ::ffff:127.0.0.1)
+    const v4Mapped = normalizedHost.match(/^::ffff:(\d+\.\d+\.\d+\.\d+)$/i);
 
-    if (v4MappedDotted) {
-      return isPrivateUrl(`http://${v4MappedDotted[1]}`);
-    }
-
-    // IPv4-mapped IPv6, hex form (e.g. ::ffff:7f00:1). `new URL()` normalizes the
-    // dotted form above to this, so it must be decoded to the embedded IPv4 as
-    // well - otherwise a literal host such as `http://[::ffff:127.0.0.1]` slips
-    // through every dotted-decimal check above (SSRF, see #2901).
-    const v4MappedHex = normalizedHost.match(/^::ffff:([0-9a-f]{1,4}):([0-9a-f]{1,4})$/i);
-
-    if (v4MappedHex) {
-      const high = parseInt(v4MappedHex[1], 16);
-      const low = parseInt(v4MappedHex[2], 16);
-      const ipv4 = [high >> 8, high & 0xff, low >> 8, low & 0xff].join('.');
-
-      return isPrivateUrl(`http://${ipv4}`);
+    if (v4Mapped) {
+      return isPrivateUrl(`http://${v4Mapped[1]}`);
     }
 
     return false;

packages/prisma/package.json

@@ -26,16 +26,16 @@
     "nanoid": "^5.1.6",
     "prisma": "^6.19.0",
     "prisma-extension-kysely": "^3.0.0",
+    "prisma-kysely": "^2.3.0",
+    "prisma-json-types-generator": "^3.6.2",
     "ts-pattern": "^5.9.0",
-    "zod": "^3.25.76"
+    "zod": "^3.25.76",
+    "zod-prisma-types": "3.3.5"
   },
   "devDependencies": {
     "dotenv": "^17.2.3",
     "dotenv-cli": "^11.0.0",
-    "prisma-kysely": "^2.3.0",
-    "prisma-json-types-generator": "^3.6.2",
     "tsx": "^4.23.1",
-    "typescript": "5.6.2",
-    "zod-prisma-types": "3.3.5"
+    "typescript": "5.6.2"
   }
 }

packages/signing/index.ts

@@ -1,9 +1,9 @@
 import {
-  NEXT_PRIVATE_SIGNING_TRANSPORT,
   NEXT_PRIVATE_USE_LEGACY_SIGNING_SUBFILTER,
   NEXT_PUBLIC_SIGNING_CONTACT_INFO,
   NEXT_PUBLIC_WEBAPP_URL,
 } from '@documenso/lib/constants/app';
+import { env } from '@documenso/lib/utils/env';
 import type { PDF, Signer } from '@libpdf/core';
 import { match } from 'ts-pattern';
 
@@ -22,7 +22,7 @@ const getSigner = async () => {
     return signer;
   }
 
-  const transport = NEXT_PRIVATE_SIGNING_TRANSPORT();
+  const transport = env('NEXT_PRIVATE_SIGNING_TRANSPORT') || 'local';
 
   // eslint-disable-next-line require-atomic-updates
   signer = await match(transport)
@@ -49,11 +49,6 @@ export const signPdf = async ({ pdf }: SignOptions) => {
     timestampAuthority: tsa ?? undefined,
     longTermValidation: !!tsa,
     archivalTimestamp: !!tsa,
-    // A B-LTA signature (signer chain + RFC 3161 timestamp token + LTV
-    // revocation data) can exceed the 12288-byte default placeholder,
-    // depending on the signing certificate chain and the TSA responder.
-    // The unused portion is zero-padding, so over-reserving is cheap.
-    estimatedSize: tsa ? 32768 : undefined,
   });
 
   return bytes;

packages/signing/transports/local.ts

@@ -22,20 +22,10 @@ const loadP12 = (): Uint8Array => {
   throw new Error('No certificate found for local signing');
 };
 
-export type CreateLocalSignerOptions = {
-  /**
-   * Fetch missing intermediates via AIA. Leave on for sealing.
-   * Turn off for health checks so they do not hit the network.
-   *
-   * @default true
-   */
-  buildChain?: boolean;
-};
-
-export const createLocalSigner = async ({ buildChain = true }: CreateLocalSignerOptions = {}) => {
+export const createLocalSigner = async () => {
   const p12 = loadP12();
 
   return await P12Signer.create(p12, env('NEXT_PRIVATE_SIGNING_PASSPHRASE') || '', {
-    buildChain,
+    buildChain: true,
   });
 };

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

@@ -125,7 +125,9 @@ 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,

packages/trpc/server/template-router/router.ts

@@ -22,7 +22,6 @@ import { findTemplates } from '@documenso/lib/server-only/template/find-template
 import { getOrganisationTemplateById } from '@documenso/lib/server-only/template/get-organisation-template-by-id';
 import { getTemplateById } from '@documenso/lib/server-only/template/get-template-by-id';
 import { toggleTemplateDirectLink } from '@documenso/lib/server-only/template/toggle-template-direct-link';
-import { validateBulkSendCsv } from '@documenso/lib/server-only/template/validate-bulk-send-csv';
 import { fireAndForget } from '@documenso/lib/universal/fire-and-forget';
 import { putNormalizedPdfFileServerSide } from '@documenso/lib/universal/upload/put-file.server';
 import { getPresignPostUrl } from '@documenso/lib/universal/upload/server-actions';
@@ -880,15 +879,6 @@ export const templateRouter = router({
       });
     }
 
-    const csvValidationResult = validateBulkSendCsv({
-      csvContent: csv,
-      recipientCount: template.recipients.length,
-    });
-
-    if (!csvValidationResult.success) {
-      return { success: false as const, error: csvValidationResult.error };
-    }
-
     await jobs.triggerJob({
       name: 'internal.bulk-send-template',
       payload: {
@@ -901,6 +891,6 @@ export const templateRouter = router({
       },
     });
 
-    return { success: true as const };
+    return { success: true };
   }),
 });

packages/ui/primitives/auto-sized-text.tsx

@@ -0,0 +1,143 @@
+import { useLayoutEffect, useRef } from 'react';
+
+import { cn } from '../lib/utils';
+
+export type Dimensions = {
+  height: number;
+  width: number;
+};
+
+export type AutoSizedTextProps = {
+  children: React.ReactNode;
+  className?: string;
+  maxHeight?: number;
+  useRem?: boolean;
+};
+
+const ITERATION_LIMIT = 20;
+const MAXIMUM_DIFFERENCE = 1; // px
+
+function getElementDimensions(element: HTMLElement): Dimensions {
+  const bbox = element.getBoundingClientRect();
+
+  return {
+    width: bbox.width,
+    height: bbox.height,
+  };
+}
+
+function getBaseFontSize(): number {
+  try {
+    const fontSize = getComputedStyle(document.documentElement).fontSize;
+    const parsed = parseFloat(fontSize);
+
+    // Check if we got a valid number
+    if (!Number.isFinite(parsed)) {
+      return 16;
+    }
+
+    return parsed;
+  } catch (error) {
+    // Fallback to browser default if anything goes wrong
+    return 16;
+  }
+}
+
+function pxToRem(px: number): number {
+  return px / getBaseFontSize();
+}
+
+export function AutoSizedText({ children, className, maxHeight, useRem = false }: AutoSizedTextProps) {
+  const childRef = useRef<HTMLDivElement>(null);
+
+  const fontSize = useRef<number>(0);
+  const fontSizeLowerBound = useRef<number>(0);
+  const fontSizeUpperBound = useRef<number>(0);
+
+  const adjustFontSize = (childDimensions: Dimensions, parentDimensions: Dimensions) => {
+    const childElement = childRef.current;
+
+    if (!childElement) {
+      return;
+    }
+
+    let newFontSize: number;
+
+    const targetHeight = maxHeight && maxHeight < parentDimensions.height ? maxHeight : parentDimensions.height;
+
+    const isElementTooBig = childDimensions.width > parentDimensions.width || childDimensions.height > targetHeight;
+
+    if (isElementTooBig) {
+      // Scale down if element is bigger than target
+      newFontSize = (fontSizeLowerBound.current + fontSize.current) / 2;
+      fontSizeUpperBound.current = fontSize.current;
+    } else if (childDimensions.width < parentDimensions.width || childDimensions.height < parentDimensions.height) {
+      // Scale up if element is smaller than target
+      newFontSize = (fontSizeUpperBound.current + fontSize.current) / 2;
+      fontSizeLowerBound.current = fontSize.current;
+    }
+
+    fontSize.current = newFontSize;
+
+    // Convert to rem if useRem is true
+    const displayFontSize = useRem ? `${pxToRem(newFontSize)}rem` : `${newFontSize}px`;
+    childElement.style.fontSize = displayFontSize;
+  };
+
+  useLayoutEffect(() => {
+    const childElement = childRef.current;
+    const parentElement = childRef.current?.parentElement;
+
+    if (!childElement || !parentElement) {
+      return;
+    }
+
+    const observer = new ResizeObserver((entries) => {
+      const entry = entries[0];
+
+      if (!entry) {
+        return;
+      }
+
+      const parentDimensions = entry.contentRect;
+
+      // Reset iteration parameters
+      fontSizeLowerBound.current = 0;
+      fontSizeUpperBound.current = parentDimensions.height;
+
+      let iterationCount = 0;
+
+      while (iterationCount <= ITERATION_LIMIT) {
+        const childDimensions = getElementDimensions(childElement);
+
+        const targetHeight = maxHeight && maxHeight < parentDimensions.height ? maxHeight : parentDimensions.height;
+
+        const widthDifference = parentDimensions.width - childDimensions.width;
+        const heightDifference = targetHeight - childDimensions.height;
+
+        const childFitsIntoParent = heightDifference >= 0 && widthDifference >= 0;
+        const isWithinTolerance =
+          Math.abs(widthDifference) <= MAXIMUM_DIFFERENCE || Math.abs(heightDifference) <= MAXIMUM_DIFFERENCE;
+
+        if (childFitsIntoParent && isWithinTolerance) {
+          break;
+        }
+
+        adjustFontSize(childDimensions, parentDimensions);
+        iterationCount += 1;
+      }
+    });
+
+    observer.observe(parentElement);
+
+    return () => {
+      observer.disconnect();
+    };
+  }, [maxHeight, useRem]);
+
+  return (
+    <div ref={childRef} className={cn('inline-block leading-none', className)}>
+      {children}
+    </div>
+  );
+}