diff --git a/packages/lib/server-only/envelope-item/create-envelope-items.ts b/packages/lib/server-only/envelope-item/create-envelope-items.ts
index b4e5dda38..c1cc9c429 100644
--- a/packages/lib/server-only/envelope-item/create-envelope-items.ts
+++ b/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,
diff --git a/packages/lib/server-only/envelope-item/replace-envelope-item-pdf.ts b/packages/lib/server-only/envelope-item/replace-envelope-item-pdf.ts
index fb305e311..0af19138a 100644
--- a/packages/lib/server-only/envelope-item/replace-envelope-item-pdf.ts
+++ b/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({
diff --git a/packages/lib/server-only/pdf/auto-place-fields.ts b/packages/lib/server-only/pdf/auto-place-fields.ts
index 5095e5f07..d2c807af4 100644
--- a/packages/lib/server-only/pdf/auto-place-fields.ts
+++ b/packages/lib/server-only/pdf/auto-place-fields.ts
@@ -68,7 +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[] = [];
@@ -149,6 +157,8 @@ export const extractPlaceholdersFromPDF = async (pdf: Buffer): Promise<Placehold
 
         logger.warn(
           {
+            envelopeId: logContext?.envelopeId,
+            fileName: logContext?.fileName,
             placeholder,
             page: page.index + 1,
             code: appError.code,
@@ -224,8 +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: [] };
diff --git a/packages/trpc/server/envelope-router/create-envelope.ts b/packages/trpc/server/envelope-router/create-envelope.ts
index c721ad31e..eb92dab9f 100644
--- a/packages/trpc/server/envelope-router/create-envelope.ts
+++ b/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,