diff --git a/apps/remix/server/api/files/files.ts b/apps/remix/server/api/files/files.ts
index 04588a7b2..a27ec4d8e 100644
--- a/apps/remix/server/api/files/files.ts
+++ b/apps/remix/server/api/files/files.ts
@@ -11,6 +11,7 @@ import { Hono } from 'hono';
 import type { HonoEnv } from '../../router';
 import { checkEnvelopeFileAccess, handleEnvelopeItemFileRequest, resolveFileUploadUserId } from './files.helpers';
 import {
+  type TUploadPdfResponse,
   ZGetEnvelopeItemFileDownloadRequestParamsSchema,
   ZGetEnvelopeItemFileRequestParamsSchema,
   ZGetEnvelopeItemFileRequestQuerySchema,
@@ -51,9 +52,13 @@ export const filesRoute = new Hono<HonoEnv>()
         return c.json({ error: 'File too large' }, 400);
       }
 
-      const result = await putNormalizedPdfFileServerSide(file);
+      const { documentData } = await putNormalizedPdfFileServerSide(file);
 
-      return c.json(result);
+      // Typed so the response cannot drift from the shape `putPdfFile` reads
+      // on the client.
+      const response: TUploadPdfResponse = documentData;
+
+      return c.json(response);
     } catch (error) {
       console.error('Upload failed:', error);
       return c.json({ error: 'Upload failed' }, 500);
diff --git a/packages/api/v1/implementation.ts b/packages/api/v1/implementation.ts
index 91d6be1df..62aa410a1 100644
--- a/packages/api/v1/implementation.ts
+++ b/packages/api/v1/implementation.ts
@@ -818,7 +818,7 @@ export const ApiContractV1Implementation = tsr.router(ApiContractV1, {
         formValues: body.formValues,
       });
 
-      const newDocumentData = await putNormalizedPdfFileServerSide({
+      const { documentData: newDocumentData } = await putNormalizedPdfFileServerSide({
         name: fileName,
         type: 'application/pdf',
         arrayBuffer: async () => Promise.resolve(prefilled),
diff --git a/packages/app-tests/e2e/api/v2/envelope-copy-contents.spec.ts b/packages/app-tests/e2e/api/v2/envelope-copy-contents.spec.ts
index d627f4db5..4be3e8846 100644
--- a/packages/app-tests/e2e/api/v2/envelope-copy-contents.spec.ts
+++ b/packages/app-tests/e2e/api/v2/envelope-copy-contents.spec.ts
@@ -2,8 +2,12 @@ import fs from 'node:fs';
 import path from 'node:path';
 import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
 import { createApiToken } from '@documenso/lib/server-only/public-api/create-api-token';
-import { EnvelopeContentType, type TEnvelopeContentMetaInput } from '@documenso/lib/types/envelope-content-meta';
-import { nanoid } from '@documenso/lib/universal/id';
+import {
+  EnvelopeContentType,
+  type TEnvelopeContentMetaInput,
+  ZEnvelopeContentMetaSchema,
+} from '@documenso/lib/types/envelope-content-meta';
+import { generateDatabaseId, nanoid } from '@documenso/lib/universal/id';
 import { mapSecondaryIdToTemplateId } from '@documenso/lib/utils/envelope';
 import { prisma } from '@documenso/prisma';
 import { seedUser } from '@documenso/prisma/seed/users';
@@ -33,6 +37,9 @@ test.describe.configure({
 
 const examplePdfBuffer = fs.readFileSync(path.join(__dirname, '../../../../../assets/example.pdf'));
 
+// Three pages, against the single page of `example.pdf`.
+const multiPagePdfBuffer = fs.readFileSync(path.join(__dirname, '../../../../../assets/field-font-alignment.pdf'));
+
 const textMeta = (text: string): TEnvelopeContentMetaInput => ({
   type: EnvelopeContentType.TEXT,
   page: 1,
@@ -346,6 +353,70 @@ test.describe('Copy contents to new envelopes', () => {
     expect(await prisma.documentAuditLog.count({ where: { envelopeId: sourceId } })).toBe(sourceAuditLogCount);
   });
 
+  test('envelope/use leaves behind contents on pages a custom file does not have', async ({ request }) => {
+    // A template with a three page file.
+    const createForm = new FormData();
+
+    createForm.append(
+      'payload',
+      JSON.stringify({ type: EnvelopeType.TEMPLATE, title: 'Template With Contents On Later Pages' }),
+    );
+
+    createForm.append('files', new File([multiPagePdfBuffer], 'multi-page.pdf', { type: 'application/pdf' }));
+
+    const createRes = await request.post(`${baseUrl}/envelope/create`, {
+      headers: { Authorization: `Bearer ${token}` },
+      multipart: createForm,
+    });
+
+    expect(createRes.ok(), await createRes.text()).toBeTruthy();
+
+    const { id: templateId } = (await createRes.json()) as TCreateEnvelopeResponse;
+
+    const template = await prisma.envelope.findUniqueOrThrow({
+      where: { id: templateId },
+      include: { envelopeItems: true },
+    });
+
+    // A content on its first and third page, as the editor would have placed.
+    await prisma.envelopeContent.createMany({
+      data: [1, 3].map((page) => ({
+        id: generateDatabaseId('envelope_content'),
+        envelopeId: templateId,
+        envelopeItemId: template.envelopeItems[0].id,
+        contentMeta: ZEnvelopeContentMetaSchema.parse({ ...textMeta(`On page ${page}`), page }),
+      })),
+    });
+
+    // Use it with a single page file in place of the template's own.
+    const payload: TUseEnvelopePayload = {
+      envelopeId: templateId,
+      customDocumentData: [{ identifier: 0, envelopeItemId: template.envelopeItems[0].id }],
+    };
+
+    const useForm = new FormData();
+
+    useForm.append('payload', JSON.stringify(payload));
+    useForm.append('files', new File([examplePdfBuffer], 'single-page.pdf', { type: 'application/pdf' }));
+
+    const useRes = await request.post(`${baseUrl}/envelope/use`, {
+      headers: { Authorization: `Bearer ${token}` },
+      multipart: useForm,
+    });
+
+    expect(useRes.ok(), await useRes.text()).toBeTruthy();
+
+    const { id: documentId } = (await useRes.json()) as TUseEnvelopeResponse;
+
+    // Only the page 1 content made it across, the template keeps both.
+    const copied = await getContentSummaries(documentId);
+
+    expect(copied).toHaveLength(1);
+    expect(copied[0].contentMeta).toMatchObject({ page: 1, text: 'On page 1' });
+
+    expect(await prisma.envelopeContent.count({ where: { envelopeId: templateId } })).toBe(2);
+  });
+
   test('envelope/duplicate logs nothing for a template', async ({ request }) => {
     const sourceId = await createSourceEnvelope(request, token, EnvelopeType.TEMPLATE, { withSignerFields: true });
 
diff --git a/packages/lib/server-only/document/send-document.ts b/packages/lib/server-only/document/send-document.ts
index 3bf1cc2dd..e62e150bb 100644
--- a/packages/lib/server-only/document/send-document.ts
+++ b/packages/lib/server-only/document/send-document.ts
@@ -454,7 +454,7 @@ const injectFormValuesIntoDocument = async (
     fileName = `${envelope.title}.pdf`;
   }
 
-  const newDocumentData = await putNormalizedPdfFileServerSide({
+  const { documentData: newDocumentData } = await putNormalizedPdfFileServerSide({
     name: fileName,
     type: 'application/pdf',
     arrayBuffer: async () => Promise.resolve(prefilled),
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..fa92e4654 100644
--- a/packages/lib/server-only/envelope-item/create-envelope-items.ts
+++ b/packages/lib/server-only/envelope-item/create-envelope-items.ts
@@ -53,7 +53,7 @@ export const UNSAFE_createEnvelopeItems = async ({
         buffer = await insertFormValuesInPdf({ pdf: buffer, formValues: envelope.formValues });
       }
 
-      const normalized = await normalizePdf(buffer, {
+      const { pdf: normalized } = await normalizePdf(buffer, {
         flattenForm: envelope.type !== 'TEMPLATE',
       });
 
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 427f42df2..c14896fb9 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
@@ -89,7 +89,7 @@ export const UNSAFE_replaceEnvelopeItemPdf = async ({
     buffer = await insertFormValuesInPdf({ pdf: buffer, formValues: envelope.formValues });
   }
 
-  const normalized = await normalizePdf(buffer, {
+  const { pdf: normalized } = await normalizePdf(buffer, {
     flattenForm: envelope.type !== 'TEMPLATE',
   });
 
diff --git a/packages/lib/server-only/envelope/create-envelope.ts b/packages/lib/server-only/envelope/create-envelope.ts
index 7d1b3ef36..9ae8e9ee4 100644
--- a/packages/lib/server-only/envelope/create-envelope.ts
+++ b/packages/lib/server-only/envelope/create-envelope.ts
@@ -261,7 +261,7 @@ export const createEnvelope = async ({
 
         const buffer = await getFileServerSide(documentData);
 
-        const normalizedPdf = await makeNormalizedPdf(Buffer.from(buffer), {
+        const { pdf: normalizedPdf } = await makeNormalizedPdf(Buffer.from(buffer), {
           flattenForm: type !== EnvelopeType.TEMPLATE,
         });
 
diff --git a/packages/lib/server-only/pdf/insert-page-overlay.ts b/packages/lib/server-only/pdf/insert-page-overlay.ts
index ce098d351..49f16cf04 100644
--- a/packages/lib/server-only/pdf/insert-page-overlay.ts
+++ b/packages/lib/server-only/pdf/insert-page-overlay.ts
@@ -3,6 +3,7 @@ import type { PDF } from '@libpdf/core';
 import { PDF as PDFDocument } from '@libpdf/core';
 import { groupBy, unique } from 'remeda';
 
+import { AppError, AppErrorCode } from '../../errors/app-error';
 import type { ContentImageMap } from '../../universal/content-renderer/content-renderer';
 import { insertFieldInPDFV2, type OverlayContent } from './insert-field-in-pdf-v2';
 
@@ -33,7 +34,9 @@ export const insertPageOverlays = async ({ pdfDoc, fields, contents = [], images
     const page = pdfDoc.getPage(pageNumber - 1);
 
     if (!page) {
-      throw new Error(`Page ${pageNumber} does not exist`);
+      throw new AppError(AppErrorCode.INVALID_REQUEST, {
+        message: `Page ${pageNumber} does not exist`,
+      });
     }
 
     const pageWidth = page.width;
diff --git a/packages/lib/server-only/pdf/normalize-pdf.ts b/packages/lib/server-only/pdf/normalize-pdf.ts
index d2f5b8833..eb7ad9c6b 100644
--- a/packages/lib/server-only/pdf/normalize-pdf.ts
+++ b/packages/lib/server-only/pdf/normalize-pdf.ts
@@ -2,6 +2,14 @@ import { PDF } from '@libpdf/core';
 
 import { AppError } from '../../errors/app-error';
 
+/**
+ * Normalize a PDF for storage: unlock it, flatten its layers and optionally
+ * its form.
+ *
+ * Returns the normalized bytes along with the page count, since the document
+ * is already parsed here and callers otherwise have to parse it again to
+ * learn how many pages it has.
+ */
 export const normalizePdf = async (pdf: Buffer, options: { flattenForm?: boolean } = {}) => {
   const shouldFlattenForm = options.flattenForm ?? true;
 
@@ -34,5 +42,8 @@ export const normalizePdf = async (pdf: Buffer, options: { flattenForm?: boolean
 
   const normalizedPdfBytes = await pdfDoc.save();
 
-  return Buffer.from(normalizedPdfBytes);
+  return {
+    pdf: Buffer.from(normalizedPdfBytes),
+    pageCount: pdfDoc.getPageCount(),
+  };
 };
diff --git a/packages/lib/server-only/template/create-document-from-template.ts b/packages/lib/server-only/template/create-document-from-template.ts
index 16651c463..693cd8ab4 100644
--- a/packages/lib/server-only/template/create-document-from-template.ts
+++ b/packages/lib/server-only/template/create-document-from-template.ts
@@ -451,6 +451,13 @@ export const createDocumentFromTemplate = async ({
   // Value = duplicated envelope item ID.
   const oldEnvelopeItemToNewEnvelopeItemIdMap: Record<string, string> = {};
 
+  // Key = original envelope item ID
+  // Value = the page count of the custom file which replaced its PDF.
+  //
+  // Only items given a custom file are counted, since the template's own
+  // files have the pages its contents were placed on.
+  const replacedEnvelopeItemPageCounts = new Map<string, number>();
+
   // Duplicate the envelope item data.
   // Note: This is duplicated in createDocumentFromDirectTemplate
   const envelopeItemsToCreate = await Promise.all(
@@ -496,7 +503,7 @@ export const createDocumentFromTemplate = async ({
 
       // The copy keeps the source as its initial data, so the two share the
       // stored file rather than re-uploading it.
-      const newDocumentData = await putNormalizedPdfFileServerSide(
+      const { documentData: newDocumentData, filePageCount } = await putNormalizedPdfFileServerSide(
         {
           name: titleToUse,
           type: 'application/pdf',
@@ -507,6 +514,10 @@ export const createDocumentFromTemplate = async ({
         },
       );
 
+      if (foundCustomDocumentData) {
+        replacedEnvelopeItemPageCounts.set(item.id, filePageCount);
+      }
+
       const newEnvelopeItemId = prefixedId('envelope_item');
 
       oldEnvelopeItemToNewEnvelopeItemIdMap[item.id] = newEnvelopeItemId;
@@ -583,11 +594,18 @@ export const createDocumentFromTemplate = async ({
 
   const envelopeId = prefixedId('envelope');
 
+  // Trim the contents if the replaced PDF has fewer pages than the content's page.
+  const contentsToCopy = template.contents.filter((content) => {
+    const replacedPageCount = replacedEnvelopeItemPageCounts.get(content.envelopeItemId);
+
+    return replacedPageCount === undefined || content.contentMeta.page <= replacedPageCount;
+  });
+
   // The template's contents are remapped onto the new envelope items up front
   // so they can be inserted as soon as the envelope exists.
   const contentsToCreate = includeContents
     ? buildEnvelopeContentCopyData({
-        contents: template.contents,
+        contents: contentsToCopy,
         envelopeId,
         envelopeItemIdMap: oldEnvelopeItemToNewEnvelopeItemIdMap,
       })
diff --git a/packages/lib/types/envelope-content-meta.ts b/packages/lib/types/envelope-content-meta.ts
index 776e411fd..0ce12fbc4 100644
--- a/packages/lib/types/envelope-content-meta.ts
+++ b/packages/lib/types/envelope-content-meta.ts
@@ -54,7 +54,11 @@ export const ZContentLetterSpacingSchema = z
  * All content geometry is percentage based (0-100) relative to the page, unlike
  * fields which are stored in page units and clamped separately.
  */
-export const ZContentPageNumberSchema = z.number().min(1).describe('The page number the content will be on.');
+export const ZContentPageNumberSchema = z
+  .number()
+  .int()
+  .min(1)
+  .describe('The page number the content will be on. Starts from 1.');
 
 export const ZContentPercentageSchema = z.number().min(0).max(100);
 
diff --git a/packages/lib/universal/upload/put-file.server.ts b/packages/lib/universal/upload/put-file.server.ts
index 991ecd658..3ef0cd011 100644
--- a/packages/lib/universal/upload/put-file.server.ts
+++ b/packages/lib/universal/upload/put-file.server.ts
@@ -66,6 +66,9 @@ type PutNormalizedPdfFileOptions = {
 
 /**
  * Uploads a pdf file and normalizes it.
+ *
+ * Returns the created document data and the file's page count, in the same
+ * shape as `putPdfFileServerSide`.
  */
 export const putNormalizedPdfFileServerSide = async (
   file: File,
@@ -73,21 +76,26 @@ export const putNormalizedPdfFileServerSide = async (
 ) => {
   const buffer = Buffer.from(await file.arrayBuffer());
 
-  const normalized = await normalizePdf(buffer, normalizePdfOptions);
+  const { pdf: normalized, pageCount } = await normalizePdf(buffer, normalizePdfOptions);
 
   const fileName = file.name.endsWith('.pdf') ? file.name : `${file.name}.pdf`;
 
-  const documentData = await putFileServerSide({
+  const uploadedFile = await putFileServerSide({
     name: fileName,
     type: 'application/pdf',
     arrayBuffer: async () => Promise.resolve(normalized),
   });
 
-  return await createDocumentData({
-    type: documentData.type,
-    data: documentData.data,
+  const documentData = await createDocumentData({
+    type: uploadedFile.type,
+    data: uploadedFile.data,
     initialData,
   });
+
+  return {
+    documentData,
+    filePageCount: pageCount,
+  };
 };
 
 /**
diff --git a/packages/trpc/server/document-router/create-document.ts b/packages/trpc/server/document-router/create-document.ts
index f2e84364e..c657ac377 100644
--- a/packages/trpc/server/document-router/create-document.ts
+++ b/packages/trpc/server/document-router/create-document.ts
@@ -46,7 +46,7 @@ export const createDocumentRoute = authenticatedProcedure
       });
     }
 
-    const { id: documentDataId } = await putNormalizedPdfFileServerSide({
+    const { documentData } = await putNormalizedPdfFileServerSide({
       name: file.name,
       type: 'application/pdf',
       arrayBuffer: async () => Promise.resolve(pdf),
@@ -86,14 +86,14 @@ export const createDocumentRoute = authenticatedProcedure
             page: field.pageNumber,
             positionX: field.pageX,
             positionY: field.pageY,
-            documentDataId,
+            documentDataId: documentData.id,
           })),
         })),
         folderId,
         envelopeItems: [
           {
             // If you ever allow more than 1 in this endpoint, make sure to use `maximumEnvelopeItemCount` to limit it.
-            documentDataId,
+            documentDataId: documentData.id,
           },
         ],
       },
diff --git a/packages/trpc/server/envelope-router/create-envelope.ts b/packages/trpc/server/envelope-router/create-envelope.ts
index 4e9d0edfa..0af905196 100644
--- a/packages/trpc/server/envelope-router/create-envelope.ts
+++ b/packages/trpc/server/envelope-router/create-envelope.ts
@@ -144,7 +144,7 @@ export const createEnvelopeRouteCaller = async ({
         });
       }
 
-      const normalized = await normalizePdf(pdf, {
+      const { pdf: normalized } = await normalizePdf(pdf, {
         flattenForm: type !== EnvelopeType.TEMPLATE,
       });
 
diff --git a/packages/trpc/server/envelope-router/use-envelope.ts b/packages/trpc/server/envelope-router/use-envelope.ts
index 913ed0ad6..a3ef541ad 100644
--- a/packages/trpc/server/envelope-router/use-envelope.ts
+++ b/packages/trpc/server/envelope-router/use-envelope.ts
@@ -76,13 +76,13 @@ export const useEnvelopeRoute = authenticatedProcedure
     const uploadedFiles = await Promise.all(
       filesToUpload.map(async (file) => {
         // We disable flattening here since `createDocumentFromTemplate` will handle it.
-        const { id: documentDataId } = await putNormalizedPdfFileServerSide(file, {
+        const { documentData } = await putNormalizedPdfFileServerSide(file, {
           flattenForm: false,
         });
 
         return {
           name: file.name,
-          documentDataId,
+          documentDataId: documentData.id,
         };
       }),
     );
diff --git a/packages/trpc/server/template-router/router.ts b/packages/trpc/server/template-router/router.ts
index c8aeafa64..22cba6954 100644
--- a/packages/trpc/server/template-router/router.ts
+++ b/packages/trpc/server/template-router/router.ts
@@ -237,7 +237,7 @@ export const templateRouter = router({
 
       const pdf = await convertToPdf(file, ctx.logger);
 
-      const { id: templateDocumentDataId } = await putNormalizedPdfFileServerSide(
+      const { documentData: templateDocumentData } = await putNormalizedPdfFileServerSide(
         {
           name: file.name,
           type: 'application/pdf',
@@ -263,7 +263,7 @@ export const templateRouter = router({
           title,
           envelopeItems: [
             {
-              documentDataId: templateDocumentDataId,
+              documentDataId: templateDocumentData.id,
             },
           ],
           folderId,