Comparison

Fill and Sign Documents vs Winthrop

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

Fill and Sign Documents

This app allows users to fill out, sign, and manage PDF documents digitally. It supports creating electronic signatures, requesting signatures from others, and securely storing signed contracts with audit trails. Users can also scan documents and convert them into editable digital files.

Highlights
  • Fill PDF forms
  • Create digital signatures
  • Request e-signatures
  • Annotate and stamp PDFs
  • Scan and convert documents
  • Secure document management
  • Audit trails for contracts
Features
Read full description

Stop printing, scanning, and chasing down signatures. Trusted by 2 million+ users, Fill turns your iPhone / iPad into a complete PDF and signature workspace - fill out any form, eSign PDFs, assign fields to multiple signers, track audit trail live, convert file formats and send legally binding agreements in just 3 taps. ESIGN DOCUMENTS - LEGALLY BINDING, ANYWHERE Create a secure digital signature and sign documents wherever you are. eSign PDF, contracts, agreements and forms - legally binding and court-admissible • Draw, type or upload your signature • Store and reuse signature across documents • Keep paperwork moving without printing or scanning • Full audit trail for legal compliance and traceability FILL OUT FORMS IN MINUTES Complete forms digitally without printing paperwork. Add text, checkboxes, dates, initials and signatures directly to your documents. • Fill out tax forms: 1040, W-9, W-4, and more • Complete rental agreements, lease forms, and real estate files • Finish university or job applications, registration forms and medical paperwork • Choose from pre-built templates - fill, sign and share immediately • Reuse saved information across multiple documents ASSIGN FIELDS & COLLECT SIGNATURES FROM MULTIPLE SIGNERS Send one document to multiple people and assign exactly who fills what and where. Watch progress live as each person completes their part. No chasing, no confusion, no follow-up emails! • Assign specific form fields and signature blocks to each signer so that no one sign in the wrong place • Send to clients, employees, partners, or teams in one go • Track live progress of who has filled, signed, or is still pending • Manage multi-party agreements, contracts and onboarding docs from one place PDF EDITOR FOR EVERYDAY DOCUMENTS Edit, annotate and prepare documents before sharing or adding esign, no desktop needed. • Add text, annotations, highlights, stamps and comments • Merge, split, reorder and add pages to any PDF SCAN DOCUMENTS WITH YOUR CAMERA Turn paper documents into digital files instantly, no separate scanner app needed. Scan documents on the go to fill, edit or signing them digitally. • Scan receipts, forms, contracts and multipage documents • Auto-detect document edges for clean, straight results CONVERT FILES TO PDF Convert any file into PDF for easier signing and editing. Export completed PDF in any file format you need. • Convert JPG, PNG and other images to PDF • Export completed forms in multiple file format • Import & export via Google Drive, Dropbox, iCloud and email SECURE, COMPLIANT & PAPERLESS Fill helps individuals and businesses manage documents securely while reducing paperwork. • 256-bit AES military-grade encryption on every file • Full esign records and audit history for every document • GDPR, HIPAA and GLBA compliant, built for regulated industries • Legally recognised eSignature • Secure document storage and sharing from anywhere WHO USES FILL? • HR teams handling onboarding documents • Real estate agents processing lease agreements • Freelancers sending proposals • Small businesses managing approvals & multi-party agreements • Professionals signing contracts or agreements • Students completing applications & registration forms • Anyone who needs to fill, sign and send documents without printing HOW IT WORKS? 1. Import or scan a document 2. Fill forms, assign fields and prepare the file 3. Add your sign or request signatures from others 4. Collaborate with multiple signers when needed 5. Share, download or save completed documents Download Fill - start your 7 day free trial. The easiest way to fill forms, eSign doc, assign fields to multiple signers, track live progress, edit PDF, scan paperwork & convert files, all from one secure app on your iPhone / iPad. Subscribe for full access to all premium features. Subscriptions automatically renew unless auto-renewal is turned off at least 24 hours before the end of subscription period. Terms - https://www.fillhq.com/terms

About

Winthrop

Features
Read full description

Winthrop Financial Planning are proud to offer the Winthrop App. Securely store your most important files and access them at any time within your app. Protect your most personal data using enterprise-graded, encrypted security. Protected by ultra-secure, state-of-the-art technology, all your documents are available to you, wherever you are, offering you the value of secure collaboration and information sharing, to aid you in your life and financial planning.

Screenshots

Fill and Sign Documents4 screens
Winthrop3 screens

Verdict

The call

The clearest difference is in-app purchases: Winthrop at none against Fill and Sign Documents's 10. Winthrop also leads on ads (none vs shown) and iOS requirement (15.0 vs 17.0). Fill and Sign Documents's advantage is update cadence (every 3 weeks vs every 8 months). On price and device support there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. Fill and Sign Documents sells 8 in-app purchases, starting at $4.99 per 7 days. Winthrop asks for nothing beyond the download.

UpkeepUpdate frequency

Fill and Sign Documents ships an update every 3 weeks, Winthrop every 8 months. The most recent releases landed on November 2, 2026 and October 25, 2026 respectively.

Scorecard4 real differences · 6 level
Fill and Sign Documents versus Winthrop: the parameters behind the verdict, then further details
ParameterFill and Sign DocumentsWinthrop
PriceFreeFree
Rating4.3 (5.2K ratings) — better—
Positive reviews24.9% of reviews—
Number of ratings5.2K — better—
Update frequencyEvery 3 weeks — betterEvery 8 months
AdsYesNo — better
In-app purchasesYesNo — better
MonetizationFree with in-app purchases—
DevicesiPhone, iPadiPhone, iPad, iPod — better
Requires iOS17.015.0 — better
Further details — not scored
Size100 MB3 MB
Age rating4+4+
DeveloperCrowded RoadMy Wealth Cloud

Bugs and requests

Fill and Sign Documents

Reported bugs

4 issues
  • App crashes frequently
  • Text formatting issues
  • Signature feature not working as expected
  • Subscription charges despite cancellation attempts

Requested features

4 requests
  • Improve subscription cancellation process
  • Offer more affordable pricing options
  • Fix bugs and improve overall stability
  • Enhance document export and sharing capabilities

Winthrop

Not enough reviews yet to summarise bugs or requests.

In-app purchases

8 purchases

Fill and Sign Documents

Subscriptions7
  • Fill and Sign PDF Expert$4.997 Days
  • Fill Plan - Free for 7 days7 Days trial$14.991 Month
  • Fill, Edit and eSign PDF Form7 Days trial2 variants$14.991 Month
Show 4 more
  • Fill and Sign Now: PDF Editor7 Days trial$59.991 Year
  • Fill and Sign Now: PDF Filler7 Days trial2 variants$79.991 Year
  • Fill and Sign Plus: PDF Editor7 Days trial$119.991 Year
  • Fill and Sign Pro: PDF Editor7 Days trial$119.991 Year
One-time1
  • Fill Plus: Edit PDF & Sign Now$0.99
None

Winthrop

No in-app purchases

Questions

Is Fill and Sign Documents free?
Fill and Sign Documents is free to download, with in-app purchases available.
Is Winthrop free?
Winthrop is free to download, with no in-app purchases.
Do Fill and Sign Documents or Winthrop have ads?
Fill and Sign Documents shows ads; Winthrop does not.
Which is updated more often, Fill and Sign Documents or Winthrop?
Fill and Sign Documents ships an update every 3 weeks, and Winthrop every 8 months. Most recently, Fill and Sign Documents was updated on November 2, 2026 and Winthrop on October 25, 2026.

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