Upload Documents to a Request
Upload Documents to a Request
How to add, prepare and manage files inside an existing signature request
Upload one or more files into a signature request so signers can review and sign. This page explains supported file types, size considerations, ordering, metadata, signer uploads, and best practices to ensure fields snap into place where you expect.
What you'll learn
Upload to a signature request
Add single or multiple files into an already-created signature request. Files are relayed to the external document service for processing.
Signer-supplied documents
Allow signers to upload documents (signer document requests) that attach to the signature request for review and signature.
Ordering & metadata
Control document order, attach descriptive metadata/tags, add optional passwords/initials settings, and choose whether to parse anchor text for automatic field placement.
Replace & update files
Replace an existing document with a new version while preserving or re-applying fields and anchors.
Supported formats & limits
Which formats work best, what to avoid, sizing guidance and how to handle very large uploads.
Field placement best practices
How to prepare documents so signature, initials and data fields land exactly where you want them.
Always create the signature request first
Documents must be uploaded into an existing signature request. Create the request (in draft) before uploading signable documents or adding signers—this ensures documents are associated with the correct workflow and signer order.
Quick overview
- You upload signable or attachment files into a signature request that already exists.
- Uploaded files are relayed to the document processing service (YouSign) for storage and field parsing.
- You can upload one file at a time or multiple files; you can also replace files after upload.
- Prepare your documents to make field placement accurate (PDFs are usually the most reliable).
Workflow: Prepare a signature request to receive documents
Step 1 — Confirm or create the signature request
Make sure the signature request exists and is in draft or editable state. You cannot attach signable documents to a request that has already been finalized or sent.
Step 2 — Gather and review files
Collect the documents you want signers to receive. Use high-quality PDFs when possible. If you have scans, ensure pages are oriented correctly, text is readable, and images are not heavily compressed.
Step 3 — Decide ordering & merging strategy
Decide whether to upload files separately (keeps them as distinct documents inside the request) or merge them into a single PDF (keeps all pages contiguous). Consider downstream field placement and signer expectations.
Step 4 — Add descriptive metadata
Before uploading, choose meaningful filenames and attach any descriptive metadata or tags (for example: “Contract — Acme — May 2026”). This makes it easier to identify documents in the request and in audit records.
Step 5 — Upload the files
Use your platform’s document upload action to add each file to the signature request. For each file choose whether it should be treated as a signable document (fields can be added) or as an attachment (informational).
Step 6 — Confirm upload & preview
After upload, download or preview the uploaded documents from the request to verify that pages and orientation are correct and that text/images rendered as expected.
Step 7 — Add fields and anchors
Place signature/initial/date/checkbox/text fields, or enable anchor parsing so predefined text markers in the document are replaced by fields automatically. Verify on each page.
Step 8 — Final checks and activation
Confirm signer order, field placements, and notifications. When ready, activate or send the signature request so signers get their invites.
Use a short, descriptive filename
Include customer name, document type and date in the filename. This improves clarity in the request list and makes audit CSVs and downloads easier to manage.
Workflow: Upload one or multiple documents into an existing signature request
Step 1 — Choose signable vs attachment
For each file decide: should signers sign this document, or is it an attachment for reference? Mark files intended for signatures as signable so you can add fields.
Step 2 — Upload a single file
Select the file and use the upload action to attach it to the request. Wait for confirmation that the file completed uploading before moving to the next.
Step 3 — Upload multiple files (sequentially)
Repeat the single-file upload for each additional document. The uploaded documents will appear in the request in the order you added them unless you explicitly set position/ordering.
Step 4 — Insert after / reorder documents
If you want a new file to appear between existing documents, use the request’s re-ordering option (insert after / move) to place it where needed. Reordering preserves each document as a separate unit.
Step 5 — Option: merge before upload
If you prefer a single continuous document, merge files locally into a single PDF and then upload that PDF instead of multiple separate uploads.
Step 6 — Verify parsing options
If your platform supports automatic anchor parsing, enable it for documents that contain anchor texts (e.g., or specific marker text). Confirm anchors were detected and fields added.
Step 7 — Check each uploaded document
Open each uploaded document in preview mode and check page order, orientation, and legibility. Re-upload or replace if anything looks off.
Prefer PDF for complex layouts
PDF is the most predictable for maintaining fonts, layout, and page breaks. If you upload Word or image files, they may be converted — check the preview carefully.
File size & format limits
Many platforms enforce per-file size limits and may reject encrypted or password-protected files. If an upload fails with a “file too large” or similar error, split or compress the file, or ask the signer to submit a smaller scan. If you use password protection, provide the password at upload time or remove the protection.
Workflow: Signer-supplied documents (requesting uploads from a signer)
Step 1 — Add a signer document request
Add a “request documents from signer” step inside your signature request and indicate which signer should upload. This attaches a document slot that the signer can fill.
Step 2 — Explain required files to signer
In your signer message provide clear instructions (accepted formats, maximum size, naming conventions) so signers upload usable files on the first try.
Step 3 — Signer uploads their file
Signer follows the upload link, selects a file, and submits it. The file becomes attached to the signature request for the reviewing parties.
Step 4 — Review uploaded signer file
After the signer uploads, preview and confirm the document. If the file is unusable (low quality, wrong pages), ask the signer to re-upload or replace it.
Step 5 — Add fields or route the file
If the signer-supplied document needs signable fields, add them to that document. If it’s an attachment, move it into the right place for review.
Step 6 — Finalize or continue the workflow
Continue with the normal signature workflow (send reminders, finalize) after verifying signer-supplied documents are correct.
Workflow: Replace an existing document in a signature request
Step 1 — Identify the document to replace
Open the signature request, view the documents list, and select the document you want to replace. Confirm whether fields were already placed on the original.
Step 2 — Prepare the replacement file
Ensure the replacement has the same page count and layout where possible. If page positions shift, fields may need to be re-applied.
Step 3 — Upload the replacement
Use the replace action to submit the new file. The system will swap the file inside the request.
Step 4 — Verify fields & anchors
Check whether existing fields were preserved and remain aligned. If not, re-position or re-create fields as needed. Use anchor text to auto-place fields if helpful.
Step 5 — Re-activate the request (if needed)
If the request was paused or returned to draft for the replacement, re-send or re-activate so signers resume the process.
- Keeps documents distinct (useful for contracts + exhibits).
- Easier to replace individual files without affecting others.
- Field placement is per-document (page numbers restart per document).
- Best when documents represent different logical units.
Before (raw scans or Word documents)
- Mixed page sizes and orientations
- Invisible form fields or comments
- Missing fonts or layout shifts after conversion
- Large image-only PDFs with low contrast
After (prepared PDFs)
- Consistent page sizes & orientation
- Fonts embedded or converted to outlines
- Anchor markers where you want fields placed
- Optimized (compressed where needed) for upload and processing
Use anchor markers for repeatable placement
If you have many documents with the same layout, insert consistent anchor text (e.g., SIGN_HERE or /sig/) where signatures should go. Enabling automatic anchor parsing will place fields at those markers, saving manual work.
Flatten any editable form fields before upload
If a source PDF contains existing interactive form fields (from a form editor), flatten them so they appear as part of the page. Interactive form fields can interfere with adding signature fields or cause alignment issues.
Common mistakes that break field placement
- Uploading compressed low-resolution scans: fields may appear misaligned.
- Changing page counts or margins during replacement: existing fields may no longer match.
- Using password-protected files without providing the password: upload will fail or the document will be unusable.
- Relying on Word/Office conversions without previewing: conversions can shift layout and break anchors.
Supported file types and conversions
- Best: PDF (keeps layout and fonts predictable).
- Also commonly accepted: JPEG/PNG/TIFF images and standard office formats (Word). If you upload Word or image formats they are usually converted to PDF for signing—always preview after upload.
- Avoid: encrypted/password-protected documents unless you supply the password or remove protection.
Note: exact supported formats and size limits may vary by plan or workspace. If an upload is rejected for size or format, split the document or convert it to an optimized PDF and retry.
Metadata & processing options
Descriptive names & tags
Use descriptive filenames and tags so documents are easily identified in the request and audit exports.
Ordering & insertion
Place a document at a specific position in the request (insert between documents) to control signer flow.
Anchor parsing
If you include anchor markers in the document, enable parsing so fields are added automatically at those markers.
Password & initials options
If a document requires a password to open or an initials setting, provide those at upload time or prepare the document without encryption.
Replace vs re-upload
Replace an existing document to keep the request structure intact; re-upload when you want a new separate document item.
Signer-document routing
Ask specific signers to upload documents and route them for review or signing as part of the same request.
Frequently Asked Questions
When something goes wrong
If an upload fails: check file size and format first, preview the file locally, attempt an optimized PDF save, and retry. If the system returns an error about encryption or unreadable content, remove protection and re-upload. Contact support with the document filename and timestamp if the issue persists.
Ready to add documents?
Follow the steps above to upload and prepare documents before sending your signature request. If you need help preparing a PDF or designing anchors, reach out to support.