refactor: improve logger for wrong pdf placeholders

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

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

apps/docs/content/docs/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">

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

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