chore: modularize PDF processing by extracting helper functions

packages/app-tests/e2e/auto-placing-fields/auto-place-fields-document.spec.ts

@@ -1,33 +1,50 @@
-import { expect, test } from '@playwright/test';
+import { type Page, expect, test } from '@playwright/test';
 import path from 'path';
 
 import { seedUser } from '@documenso/prisma/seed/users';
 
 import { apiSignin } from '../fixtures/authentication';
 
-const PLACEHOLDER_PDF_PATH = path.join(
+const SINGLE_PLACEHOLDER_PDF_PATH = path.join(
   __dirname,
   '../../../assets/project-proposal-single-recipient.pdf',
 );
+
+const MULTIPLE_PLACEHOLDER_PDF_PATH = path.join(
+  __dirname,
+  '../../../assets/project-proposal-multiple-fields-and-recipients.pdf',
+);
+
+const setupUserAndSignIn = async (page: Page) => {
+  const { user, team } = await seedUser();
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/t/${team.url}/documents`,
+  });
+
+  return { user, team };
+};
+
+const uploadPdfAndContinue = async (page: Page, pdfPath: string, continueClicks: number = 1) => {
+  const fileInput = page.locator('input[type="file"]').nth(1);
+  await fileInput.waitFor({ state: 'attached' });
+  await fileInput.setInputFiles(pdfPath);
+
+  await page.waitForTimeout(3000);
+
+  for (let i = 0; i < continueClicks; i++) {
+    await page.getByRole('button', { name: 'Continue' }).click();
+  }
+};
+
 test.describe('PDF Placeholders with single recipient', () => {
   test('[AUTO_PLACING_FIELDS]: should automatically create recipients from PDF placeholders', async ({
     page,
   }) => {
-    const { user, team } = await seedUser();
+    await setupUserAndSignIn(page);
-
+    await uploadPdfAndContinue(page, SINGLE_PLACEHOLDER_PDF_PATH, 1);
-    await apiSignin({
-      page,
-      email: user.email,
-      redirectPath: `/t/${team.url}/documents`,
-    });
-
-    const fileInput = page.locator('input[type="file"]').nth(1);
-    await fileInput.waitFor({ state: 'attached' });
-    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
-
-    await page.waitForTimeout(3000);
-
-    await page.getByRole('button', { name: 'Continue' }).click();
 
     await expect(page.getByRole('heading', { name: 'Add Signers' })).toBeVisible();
     await expect(page.getByPlaceholder('Email')).toHaveValue('recipient.1@documenso.com');
@@ -37,22 +54,8 @@ test.describe('PDF Placeholders with single recipient', () => {
   test('[AUTO_PLACING_FIELDS]: should automatically place fields from PDF placeholders', async ({
     page,
   }) => {
-    const { user, team } = await seedUser();
+    await setupUserAndSignIn(page);
-
+    await uploadPdfAndContinue(page, SINGLE_PLACEHOLDER_PDF_PATH, 2);
-    await apiSignin({
-      page,
-      email: user.email,
-      redirectPath: `/t/${team.url}/documents`,
-    });
-
-    const fileInput = page.locator('input[type="file"]').nth(1);
-    await fileInput.waitFor({ state: 'attached' });
-    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
-
-    await page.waitForTimeout(3000);
-
-    await page.getByRole('button', { name: 'Continue' }).click();
-    await page.getByRole('button', { name: 'Continue' }).click();
 
     await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
 
@@ -65,22 +68,8 @@ test.describe('PDF Placeholders with single recipient', () => {
   test('[AUTO_PLACING_FIELDS]: should automatically configure fields from PDF placeholders', async ({
     page,
   }) => {
-    const { user, team } = await seedUser();
+    await setupUserAndSignIn(page);
-
+    await uploadPdfAndContinue(page, SINGLE_PLACEHOLDER_PDF_PATH, 2);
-    await apiSignin({
-      page,
-      email: user.email,
-      redirectPath: `/t/${team.url}/documents`,
-    });
-
-    const fileInput = page.locator('input[type="file"]').nth(1);
-    await fileInput.waitFor({ state: 'attached' });
-    await fileInput.setInputFiles(PLACEHOLDER_PDF_PATH);
-
-    await page.waitForTimeout(3000);
-
-    await page.getByRole('button', { name: 'Continue' }).click();
-    await page.getByRole('button', { name: 'Continue' }).click();
 
     await page.getByText('Text').nth(1).click();
     await page.getByRole('button', { name: 'Advanced settings' }).click();
@@ -96,3 +85,45 @@ test.describe('PDF Placeholders with single recipient', () => {
     await expect(page.getByRole('combobox')).toHaveText('Right');
   });
 });
+
+test.describe('PDF Placeholders with multiple recipients', () => {
+  test('[AUTO_PLACING_FIELDS]: should automatically create recipients from PDF placeholders', async ({
+    page,
+  }) => {
+    await setupUserAndSignIn(page);
+    await uploadPdfAndContinue(page, MULTIPLE_PLACEHOLDER_PDF_PATH, 1);
+
+    await expect(page.getByTestId('signer-email-input').first()).toHaveValue(
+      'recipient.1@documenso.com',
+    );
+    await expect(page.getByLabel('Name').first()).toHaveValue('Recipient 1');
+
+    await expect(page.getByTestId('signer-email-input').nth(1)).toHaveValue(
+      'recipient.2@documenso.com',
+    );
+    await expect(page.getByLabel('Name').nth(1)).toHaveValue('Recipient 2');
+
+    await expect(page.getByTestId('signer-email-input').nth(2)).toHaveValue(
+      'recipient.3@documenso.com',
+    );
+    await expect(page.getByLabel('Name').nth(2)).toHaveValue('Recipient 3');
+  });
+
+  test('[AUTO_PLACING_FIELDS]: should automatically create fields from PDF placeholders', async ({
+    page,
+  }) => {
+    await setupUserAndSignIn(page);
+    await uploadPdfAndContinue(page, MULTIPLE_PLACEHOLDER_PDF_PATH, 2);
+
+    await expect(page.getByRole('heading', { name: 'Add Fields' })).toBeVisible();
+
+    await expect(page.locator('[data-field-type="SIGNATURE"]').first()).toBeVisible();
+    await expect(page.locator('[data-field-type="SIGNATURE"]').nth(1)).toBeVisible();
+    await expect(page.locator('[data-field-type="SIGNATURE"]').nth(2)).toBeVisible();
+    await expect(page.locator('[data-field-type="EMAIL"]').first()).toBeVisible();
+    await expect(page.locator('[data-field-type="EMAIL"]').nth(1)).toBeVisible();
+    await expect(page.locator('[data-field-type="NAME"]')).toBeVisible();
+    await expect(page.locator('[data-field-type="TEXT"]')).toBeVisible();
+    await expect(page.locator('[data-field-type="NUMBER"]')).toBeVisible();
+  });
+});

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

@@ -1,21 +1,22 @@
 import { PDFDocument, rgb } from '@cantoo/pdf-lib';
 import type { Recipient } from '@prisma/client';
-import { EnvelopeType, FieldType, RecipientRole } from '@prisma/client';
 import PDFParser from 'pdf2json';
-import { match } from 'ts-pattern';
 
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
 import { getEnvelopeWhereInput } from '@documenso/lib/server-only/envelope/get-envelope-by-id';
 import { createEnvelopeFields } from '@documenso/lib/server-only/field/create-envelope-fields';
-import { createDocumentRecipients } from '@documenso/lib/server-only/recipient/create-document-recipients';
-import { createTemplateRecipients } from '@documenso/lib/server-only/recipient/create-template-recipients';
 import { type TFieldAndMeta, ZFieldAndMetaSchema } from '@documenso/lib/types/field-meta';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import type { EnvelopeIdOptions } from '@documenso/lib/utils/envelope';
-import { mapSecondaryIdToTemplateId } from '@documenso/lib/utils/envelope';
 import { prisma } from '@documenso/prisma';
 
 import { getPageSize } from './get-page-size';
+import {
+  createRecipientsFromPlaceholders,
+  extractRecipientPlaceholder,
+  parseFieldMetaFromPlaceholder,
+  parseFieldTypeFromPlaceholder,
+} from './helpers';
 
 type TextPosition = {
   text: string;
@@ -51,12 +52,6 @@ type FieldToCreate = TFieldAndMeta & {
   height: number;
 };
 
-type RecipientPlaceholderInfo = {
-  email: string;
-  name: string;
-  recipientIndex: number;
-};
-
 /*
   Questions for later:
     - Does it handle multi-page PDFs? ✅ YES! ✅
@@ -67,86 +62,6 @@ type RecipientPlaceholderInfo = {
     - Need to handle envelopes with multiple items. ✅
 */
 
-/*
-  Parse field type string to FieldType enum.
-  Normalizes the input (uppercase, trim) and validates it's a valid field type.
-  This ensures we handle case variations and whitespace, and provides clear error messages.
-*/
-const parseFieldType = (fieldTypeString: string): FieldType => {
-  const normalizedType = fieldTypeString.toUpperCase().trim();
-
-  return match(normalizedType)
-    .with('SIGNATURE', () => FieldType.SIGNATURE)
-    .with('FREE_SIGNATURE', () => FieldType.FREE_SIGNATURE)
-    .with('INITIALS', () => FieldType.INITIALS)
-    .with('NAME', () => FieldType.NAME)
-    .with('EMAIL', () => FieldType.EMAIL)
-    .with('DATE', () => FieldType.DATE)
-    .with('TEXT', () => FieldType.TEXT)
-    .with('NUMBER', () => FieldType.NUMBER)
-    .with('RADIO', () => FieldType.RADIO)
-    .with('CHECKBOX', () => FieldType.CHECKBOX)
-    .with('DROPDOWN', () => FieldType.DROPDOWN)
-    .otherwise(() => {
-      throw new AppError(AppErrorCode.INVALID_BODY, {
-        message: `Invalid field type: ${fieldTypeString}`,
-      });
-    });
-};
-
-/*
-  Transform raw field metadata from placeholder format to schema format.
-  Users should provide properly capitalized property names (e.g., readOnly, fontSize, textAlign).
-  Converts string values to proper types (booleans, numbers).
-*/
-const parseFieldMeta = (
-  rawFieldMeta: Record<string, string>,
-  fieldType: FieldType,
-): Record<string, unknown> | undefined => {
-  if (fieldType === FieldType.SIGNATURE || fieldType === FieldType.FREE_SIGNATURE) {
-    return;
-  }
-
-  if (Object.keys(rawFieldMeta).length === 0) {
-    return;
-  }
-
-  const fieldTypeString = String(fieldType).toLowerCase();
-
-  const parsedFieldMeta: Record<string, boolean | number | string> = {
-    type: fieldTypeString,
-  };
-
-  /*
-    rawFieldMeta is an object with string keys and string values.
-    It contains string values because the PDF parser returns the values as strings.
-
-    E.g. { 'required': 'true', 'fontSize': '12', 'maxValue': '100', 'minValue': '0', 'characterLimit': '100' }
-  */
-  const rawFieldMetaEntries = Object.entries(rawFieldMeta);
-
-  for (const [property, value] of rawFieldMetaEntries) {
-    if (property === 'readOnly' || property === 'required') {
-      parsedFieldMeta[property] = value === 'true';
-    } else if (
-      property === 'fontSize' ||
-      property === 'maxValue' ||
-      property === 'minValue' ||
-      property === 'characterLimit'
-    ) {
-      const numValue = Number(value);
-
-      if (!Number.isNaN(numValue)) {
-        parsedFieldMeta[property] = numValue;
-      }
-    } else {
-      parsedFieldMeta[property] = value;
-    }
-  }
-
-  return parsedFieldMeta;
-};
-
 export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<PlaceholderInfo[]> => {
   return new Promise((resolve, reject) => {
     const parser = new PDFParser(null, true);
@@ -221,8 +136,8 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
             fieldMetaData.map((property) => property.split('=')),
           );
 
-          const fieldType = parseFieldType(fieldTypeString);
+          const fieldType = parseFieldTypeFromPlaceholder(fieldTypeString);
-          const parsedFieldMeta = parseFieldMeta(rawFieldMeta, fieldType);
+          const parsedFieldMeta = parseFieldMetaFromPlaceholder(rawFieldMeta, fieldType);
 
           const fieldAndMeta: TFieldAndMeta = ZFieldAndMetaSchema.parse({
             type: fieldType,
@@ -288,7 +203,7 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
   });
 };
 
-export const replacePlaceholdersInPDF = async (pdf: Buffer): Promise<Buffer> => {
+export const removePlaceholdersFromPDF = async (pdf: Buffer): Promise<Buffer> => {
   const placeholders = await extractPlaceholdersFromPDF(pdf);
 
   const pdfDoc = await PDFDocument.load(new Uint8Array(pdf));
@@ -334,24 +249,6 @@ export const replacePlaceholdersInPDF = async (pdf: Buffer): Promise<Buffer> =>
   return Buffer.from(modifiedPdfBytes);
 };
 
-const extractRecipientPlaceholder = (placeholder: string): RecipientPlaceholderInfo => {
-  const indexMatch = placeholder.match(/^r(\d+)$/i);
-
-  if (!indexMatch) {
-    throw new AppError(AppErrorCode.INVALID_BODY, {
-      message: `Invalid recipient placeholder format: ${placeholder}. Expected format: r1, r2, r3, etc.`,
-    });
-  }
-
-  const recipientIndex = Number(indexMatch[1]);
-
-  return {
-    email: `recipient.${recipientIndex}@documenso.com`,
-    name: `Recipient ${recipientIndex}`,
-    recipientIndex,
-  };
-};
-
 export const insertFieldsFromPlaceholdersInPDF = async (
   pdf: Buffer,
   userId: number,
@@ -359,6 +256,7 @@ export const insertFieldsFromPlaceholdersInPDF = async (
   envelopeId: EnvelopeIdOptions,
   requestMetadata: ApiRequestMetadata,
   envelopeItemId?: string,
+  recipients?: Pick<Recipient, 'id' | 'email'>[],
 ): Promise<Buffer> => {
   const placeholders = await extractPlaceholdersFromPDF(pdf);
 
@@ -378,22 +276,6 @@ export const insertFieldsFromPlaceholdersInPDF = async (
     recipientPlaceholders.set(recipientIndex, name);
   }
 
-  /*
-    Create a list of recipients to create.
-    Example: [{ email: 'recipient.1@documenso.com', name: 'Recipient 1', role: 'SIGNER', signingOrder: 1 }]
-  */
-  const recipientsToCreate = Array.from(
-    recipientPlaceholders.entries(),
-    ([recipientIndex, name]) => {
-      return {
-        email: `recipient.${recipientIndex}@documenso.com`,
-        name,
-        role: RecipientRole.SIGNER,
-        signingOrder: recipientIndex,
-      };
-    },
-  );
-
   const { envelopeWhereInput } = await getEnvelopeWhereInput({
     id: envelopeId,
     userId,
@@ -416,53 +298,19 @@ export const insertFieldsFromPlaceholdersInPDF = async (
     });
   }
 
-  const existingRecipients = await prisma.recipient.findMany({
+  let createdRecipients: Pick<Recipient, 'id' | 'email'>[];
-    where: {
-      envelopeId: envelope.id,
-    },
-    select: {
-      id: true,
-      email: true,
-    },
-  });
 
-  const existingEmails = new Set(existingRecipients.map((r) => r.email));
+  if (recipients && recipients.length > 0) {
-  const recipientsToCreateFiltered = recipientsToCreate.filter(
+    createdRecipients = recipients;
-    (recipient) => !existingEmails.has(recipient.email),
+  } else {
-  );
+    createdRecipients = await createRecipientsFromPlaceholders(
-
+      recipientPlaceholders,
-  let createdRecipients: Pick<Recipient, 'id' | 'email'>[] = existingRecipients;
+      envelope,
-
+      envelopeId,
-  if (recipientsToCreateFiltered.length > 0) {
+      userId,
-    if (envelope.type === EnvelopeType.DOCUMENT) {
+      teamId,
-      const { recipients } = await createDocumentRecipients({
+      requestMetadata,
-        userId,
+    );
-        teamId,
-        id: envelopeId,
-        recipients: recipientsToCreateFiltered,
-        requestMetadata,
-      });
-
-      createdRecipients = [...existingRecipients, ...recipients];
-    } else if (envelope.type === EnvelopeType.TEMPLATE) {
-      const templateId =
-        envelopeId.type === 'templateId'
-          ? envelopeId.id
-          : mapSecondaryIdToTemplateId(envelope.secondaryId);
-
-      const { recipients } = await createTemplateRecipients({
-        userId,
-        teamId,
-        templateId,
-        recipients: recipientsToCreateFiltered,
-      });
-
-      createdRecipients = [...existingRecipients, ...recipients];
-    } else {
-      throw new AppError(AppErrorCode.INVALID_BODY, {
-        message: `Invalid envelope type: ${envelope.type}`,
-      });
-    }
   }
 
   const fieldsToCreate: FieldToCreate[] = [];
@@ -479,8 +327,30 @@ export const insertFieldsFromPlaceholdersInPDF = async (
     const widthPercent = (placeholder.width / placeholder.pageWidth) * 100;
     const heightPercent = (placeholder.height / placeholder.pageHeight) * 100;
 
-    const { email } = extractRecipientPlaceholder(placeholder.recipient);
+    let recipient: Pick<Recipient, 'id' | 'email'> | undefined;
-    const recipient = createdRecipients.find((r) => r.email === email);
+
+    if (recipients && recipients.length > 0) {
+      /*
+        Map placeholder by index: r1 -> recipients[0], r2 -> recipients[1], etc.
+        recipientIndex is 1-based, so we subtract 1 to get the array index.
+      */
+      const { recipientIndex } = extractRecipientPlaceholder(placeholder.recipient);
+      const recipientArrayIndex = recipientIndex - 1;
+
+      if (recipientArrayIndex < 0 || recipientArrayIndex >= recipients.length) {
+        throw new AppError(AppErrorCode.INVALID_BODY, {
+          message: `Recipient placeholder ${placeholder.recipient} (index ${recipientIndex}) is out of range. Provided ${recipients.length} recipient(s).`,
+        });
+      }
+
+      recipient = recipients[recipientArrayIndex];
+    } else {
+      /*
+        Use email-based matching for placeholder recipients.
+      */
+      const { email } = extractRecipientPlaceholder(placeholder.recipient);
+      recipient = createdRecipients.find((r) => r.email === email);
+    }
 
     if (!recipient) {
       throw new AppError(AppErrorCode.INVALID_BODY, {

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

@@ -0,0 +1,191 @@
+import { FieldType } from '@prisma/client';
+import { type Envelope, EnvelopeType, RecipientRole } from '@prisma/client';
+import type { Recipient } from '@prisma/client';
+import { match } from 'ts-pattern';
+
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { createDocumentRecipients } from '@documenso/lib/server-only/recipient/create-document-recipients';
+import { createTemplateRecipients } from '@documenso/lib/server-only/recipient/create-template-recipients';
+import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
+import { mapSecondaryIdToTemplateId } from '@documenso/lib/utils/envelope';
+import type { EnvelopeIdOptions } from '@documenso/lib/utils/envelope';
+import { prisma } from '@documenso/prisma';
+
+type RecipientPlaceholderInfo = {
+  email: string;
+  name: string;
+  recipientIndex: number;
+};
+
+/*
+  Parse field type string to FieldType enum.
+  Normalizes the input (uppercase, trim) and validates it's a valid field type.
+  This ensures we handle case variations and whitespace, and provides clear error messages.
+*/
+export const parseFieldTypeFromPlaceholder = (fieldTypeString: string): FieldType => {
+  const normalizedType = fieldTypeString.toUpperCase().trim();
+
+  return match(normalizedType)
+    .with('SIGNATURE', () => FieldType.SIGNATURE)
+    .with('FREE_SIGNATURE', () => FieldType.FREE_SIGNATURE)
+    .with('INITIALS', () => FieldType.INITIALS)
+    .with('NAME', () => FieldType.NAME)
+    .with('EMAIL', () => FieldType.EMAIL)
+    .with('DATE', () => FieldType.DATE)
+    .with('TEXT', () => FieldType.TEXT)
+    .with('NUMBER', () => FieldType.NUMBER)
+    .with('RADIO', () => FieldType.RADIO)
+    .with('CHECKBOX', () => FieldType.CHECKBOX)
+    .with('DROPDOWN', () => FieldType.DROPDOWN)
+    .otherwise(() => {
+      throw new AppError(AppErrorCode.INVALID_BODY, {
+        message: `Invalid field type: ${fieldTypeString}`,
+      });
+    });
+};
+
+/*
+  Transform raw field metadata from placeholder format to schema format.
+  Users should provide properly capitalized property names (e.g., readOnly, fontSize, textAlign).
+  Converts string values to proper types (booleans, numbers).
+*/
+export const parseFieldMetaFromPlaceholder = (
+  rawFieldMeta: Record<string, string>,
+  fieldType: FieldType,
+): Record<string, unknown> | undefined => {
+  if (fieldType === FieldType.SIGNATURE || fieldType === FieldType.FREE_SIGNATURE) {
+    return;
+  }
+
+  if (Object.keys(rawFieldMeta).length === 0) {
+    return;
+  }
+
+  const fieldTypeString = String(fieldType).toLowerCase();
+
+  const parsedFieldMeta: Record<string, boolean | number | string> = {
+    type: fieldTypeString,
+  };
+
+  /*
+    rawFieldMeta is an object with string keys and string values.
+    It contains string values because the PDF parser returns the values as strings.
+
+    E.g. { 'required': 'true', 'fontSize': '12', 'maxValue': '100', 'minValue': '0', 'characterLimit': '100' }
+  */
+  const rawFieldMetaEntries = Object.entries(rawFieldMeta);
+
+  for (const [property, value] of rawFieldMetaEntries) {
+    if (property === 'readOnly' || property === 'required') {
+      parsedFieldMeta[property] = value === 'true';
+    } else if (
+      property === 'fontSize' ||
+      property === 'maxValue' ||
+      property === 'minValue' ||
+      property === 'characterLimit'
+    ) {
+      const numValue = Number(value);
+
+      if (!Number.isNaN(numValue)) {
+        parsedFieldMeta[property] = numValue;
+      }
+    } else {
+      parsedFieldMeta[property] = value;
+    }
+  }
+
+  return parsedFieldMeta;
+};
+
+export const extractRecipientPlaceholder = (placeholder: string): RecipientPlaceholderInfo => {
+  const indexMatch = placeholder.match(/^r(\d+)$/i);
+
+  if (!indexMatch) {
+    throw new AppError(AppErrorCode.INVALID_BODY, {
+      message: `Invalid recipient placeholder format: ${placeholder}. Expected format: r1, r2, r3, etc.`,
+    });
+  }
+
+  const recipientIndex = Number(indexMatch[1]);
+
+  return {
+    email: `recipient.${recipientIndex}@documenso.com`,
+    name: `Recipient ${recipientIndex}`,
+    recipientIndex,
+  };
+};
+
+export const createRecipientsFromPlaceholders = async (
+  recipientPlaceholders: Map<number, string>,
+  envelope: Pick<Envelope, 'id' | 'type' | 'secondaryId'>,
+  envelopeId: EnvelopeIdOptions,
+  userId: number,
+  teamId: number,
+  requestMetadata: ApiRequestMetadata,
+): Promise<Pick<Recipient, 'id' | 'email'>[]> => {
+  const recipientsToCreate = Array.from(
+    recipientPlaceholders.entries(),
+    ([recipientIndex, name]) => {
+      return {
+        email: `recipient.${recipientIndex}@documenso.com`,
+        name,
+        role: RecipientRole.SIGNER,
+        signingOrder: recipientIndex,
+      };
+    },
+  );
+
+  const existingRecipients = await prisma.recipient.findMany({
+    where: {
+      envelopeId: envelope.id,
+    },
+    select: {
+      id: true,
+      email: true,
+    },
+  });
+
+  const existingEmails = new Set(existingRecipients.map((r) => r.email));
+  const recipientsToCreateFiltered = recipientsToCreate.filter(
+    (recipient) => !existingEmails.has(recipient.email),
+  );
+
+  if (recipientsToCreateFiltered.length === 0) {
+    return existingRecipients;
+  }
+
+  const newRecipients = await match(envelope.type)
+    .with(EnvelopeType.DOCUMENT, async () => {
+      const { recipients } = await createDocumentRecipients({
+        userId,
+        teamId,
+        id: envelopeId,
+        recipients: recipientsToCreateFiltered,
+        requestMetadata,
+      });
+
+      return recipients;
+    })
+    .with(EnvelopeType.TEMPLATE, async () => {
+      const templateId =
+        envelopeId.type === 'templateId'
+          ? envelopeId.id
+          : mapSecondaryIdToTemplateId(envelope.secondaryId ?? '');
+
+      const { recipients } = await createTemplateRecipients({
+        userId,
+        teamId,
+        templateId,
+        recipients: recipientsToCreateFiltered,
+      });
+
+      return recipients;
+    })
+    .otherwise(() => {
+      throw new AppError(AppErrorCode.INVALID_BODY, {
+        message: `Invalid envelope type: ${envelope.type}`,
+      });
+    });
+
+  return [...existingRecipients, ...newRecipients];
+};

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

@@ -1,6 +1,6 @@
 import { PDFDocument } from '@cantoo/pdf-lib';
 
-import { replacePlaceholdersInPDF } from './auto-place-fields';
+import { removePlaceholdersFromPDF } from './auto-place-fields';
 import { flattenAnnotations } from './flatten-annotations';
 import { flattenForm, removeOptionalContentGroups } from './flatten-form';
 
@@ -14,7 +14,7 @@ export const normalizePdf = async (pdf: Buffer) => {
   removeOptionalContentGroups(pdfDoc);
   await flattenForm(pdfDoc);
   flattenAnnotations(pdfDoc);
-  const pdfWithoutPlaceholders = await replacePlaceholdersInPDF(pdf);
+  const pdfWithoutPlaceholders = await removePlaceholdersFromPDF(pdf);
 
   return pdfWithoutPlaceholders;
 };