diff --git a/packages/lib/server-only/envelope/create-envelope.ts b/packages/lib/server-only/envelope/create-envelope.ts
index 5f4198377..b92ba2d32 100644
--- a/packages/lib/server-only/envelope/create-envelope.ts
+++ b/packages/lib/server-only/envelope/create-envelope.ts
@@ -10,6 +10,7 @@ import {
 } from '@prisma/client';
 
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { insertFieldsFromPlaceholdersInPDF } from '@documenso/lib/server-only/pdf/auto-place-fields';
 import { normalizePdf as makeNormalizedPdf } from '@documenso/lib/server-only/pdf/normalize-pdf';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
@@ -233,7 +234,7 @@ export const createEnvelope = async ({
       ? await incrementDocumentId().then((v) => v.formattedDocumentId)
       : await incrementTemplateId().then((v) => v.formattedTemplateId);
 
-  return await prisma.$transaction(async (tx) => {
+  const createdEnvelope = await prisma.$transaction(async (tx) => {
     const envelope = await tx.envelope.create({
       data: {
         id: prefixedId('envelope'),
@@ -353,8 +354,12 @@ export const createEnvelope = async ({
         recipients: true,
         fields: true,
         folder: true,
-        envelopeItems: true,
         envelopeAttachments: true,
+        envelopeItems: {
+          include: {
+            documentData: true,
+          },
+        },
       },
     });
 
@@ -390,4 +395,51 @@ export const createEnvelope = async ({
 
     return createdEnvelope;
   });
+
+  for (const envelopeItem of createdEnvelope.envelopeItems) {
+    const buffer = await getFileServerSide(envelopeItem.documentData);
+
+    // Use normalized PDF if normalizePdf was true, otherwise use original
+    const pdfToProcess = normalizePdf
+      ? await makeNormalizedPdf(Buffer.from(buffer))
+      : Buffer.from(buffer);
+
+    await insertFieldsFromPlaceholdersInPDF(
+      pdfToProcess,
+      userId,
+      teamId,
+      {
+        type: 'envelopeId',
+        id: createdEnvelope.id,
+      },
+      requestMetadata,
+      envelopeItem.id,
+    );
+  }
+
+  const finalEnvelope = await prisma.envelope.findFirst({
+    where: {
+      id: createdEnvelope.id,
+    },
+    include: {
+      documentMeta: true,
+      recipients: true,
+      fields: true,
+      folder: true,
+      envelopeAttachments: true,
+      envelopeItems: {
+        include: {
+          documentData: true,
+        },
+      },
+    },
+  });
+
+  if (!finalEnvelope) {
+    throw new AppError(AppErrorCode.NOT_FOUND, {
+      message: 'Envelope not found',
+    });
+  }
+
+  return finalEnvelope;
 };
diff --git a/packages/lib/server-only/pdf/auto-place-fields.ts b/packages/lib/server-only/pdf/auto-place-fields.ts
index ecd714e04..923c8138c 100644
--- a/packages/lib/server-only/pdf/auto-place-fields.ts
+++ b/packages/lib/server-only/pdf/auto-place-fields.ts
@@ -63,8 +63,8 @@ type RecipientPlaceholderInfo = {
     - Does it handle multiple recipients on the same page? ✅ YES! ✅
     - Does it handle multiple recipients on multiple pages? ✅ YES! ✅
     - What happens with incorrect placeholders? E.g. those containing non-accepted properties.
-    - The placeholder data is dynamic. How to handle this parsing? Perhaps we need to do it similar to the fieldMeta parsing.
-    - Need to handle envelopes with multiple items.
+    - The placeholder data is dynamic. How to handle this parsing? Perhaps we need to do it similar to the fieldMeta parsing. ✅
+    - Need to handle envelopes with multiple items. ✅
 */
 
 /*
@@ -202,9 +202,9 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
 
         const placeholderMatches = pageText.matchAll(/{{([^}]+)}}/g);
 
-        for (const match of placeholderMatches) {
-          const placeholder = match[0];
-          const placeholderData = match[1].split(',').map((part) => part.trim());
+        for (const placeholderMatch of placeholderMatches) {
+          const placeholder = placeholderMatch[0];
+          const placeholderData = placeholderMatch[1].split(',').map((part) => part.trim());
 
           const [fieldTypeString, recipient, ...fieldMetaData] = placeholderData;
 
@@ -223,7 +223,12 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
 
             Then find the position of where the placeholder ends in the text by adding the length of the placeholder to the index of the placeholder.
           */
-          const matchIndex = match.index;
+          const matchIndex = placeholderMatch.index;
+
+          if (matchIndex === undefined) {
+            continue;
+          }
+
           const placeholderLength = placeholder.length;
           const placeholderEndIndex = matchIndex + placeholderLength;