Chat with PDF

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Note: This feature is available with an active paid subscription.
Based on 12500+ reviews
Last updated on Feb 9, 2026

AI-powered Ask Documents tool

Transform how you work with PDF documents using pdfFiller's revolutionary Ask Documents feature. Our AI-powered technology lets you instantly extract information, ask questions, and get precise answers from any document—no more scrolling through pages or manual searching. Whether you're reviewing contracts, analyzing reports, or managing business or legal documents, this intelligent feature streamlines your workflow and saves hours of manual work.

Built into pdfFiller's comprehensive document management platform, Ask Documents combines cutting-edge artificial intelligence with enterprise-grade security, giving small business owners, managers, contractors, and agents the power to work smarter.

What is the AI-powered Ask Documents feature?

The Ask Documents feature is an intelligent document assistant that uses advanced AI to understand and analyze your uploaded files. Simply upload any document and ask questions in plain English—the AI instantly provides accurate answers by scanning and interpreting your content.

This powerful tool eliminates the need to manually search through lengthy documents. Whether you need specific data points, document summaries, or answers to complex questions about your files, the AI delivers precise responses in seconds, making document management effortless and efficient.

How does the Ask Documents tool work?

  1. 1.
    Upload your documents easily. Getting started is simple—just drag and drop your files into pdfFiller's secure platform. The system supports PDFs, Word documents, Excel spreadsheets, PowerPoint presentations, and many other popular formats. Once uploaded, your documents are instantly processed and ready for AI analysis. The cloud-based system means you can access your files and ask questions from any device, anywhere.
  2. 2.
    Ask questions and get instant answers. Type your questions in natural language, just like you're talking to a colleague. Ask anything from "What's the total budget in this proposal?" to "When does this contract expire?" or "Summarize the key terms in section 3.". The AI understands context and provides specific, accurate answers by analyzing the relevant sections of your document. No technical knowledge required—just ask what you need to know.
  3. 3.
    Explore detailed insights. Beyond simple Q&A, the feature offers comprehensive document analysis. Generate executive summaries, extract key data points, identify important dates and deadlines, and pull specific information for reports or presentations. The AI can analyze multiple documents simultaneously, helping you compare contracts, merge insights from different sources, or track information across your entire document library.

Why choose pdfFiller's AI assistant?

  1. 1.
    Enhance productivity. Save up to 40 hours per month by eliminating manual document review. Instead of reading through entire contracts or reports, get instant answers to specific questions. Focus your time on decision-making and strategic work rather than document hunting. The feature reduces errors by providing accurate, AI-verified information directly from your source documents, ensuring you never miss critical details or deadlines.
  2. 2.
    Improve document management. Organize and retrieve information more effectively with intelligent search capabilities. The AI remembers document contents and can help you locate specific information across your entire file collection. Create searchable knowledge bases from your documents, making institutional knowledge accessible to your entire team without manual indexing or tagging.
  3. 3.
    Ensure data protection and compliance. Your documents remain secure with enterprise-grade protection. pdfFiller maintains GDPR, HIPAA, and ESIGN compliance, ensuring your sensitive business information stays protected. All processing happens within pdfFiller's secure cloud infrastructure, with encrypted data transmission and storage. Your documents never leave the protected environment, maintaining confidentiality and regulatory compliance.

Use cases for the Ask Documents feature

  1. 1.
    For professionals: Quickly review contracts to identify key information, renewal dates, and obligations without reading every page. Extract client information from agreements, analyze proposal requirements, and prepare summaries for stakeholder meetings. Legal professionals can identify specific clauses, compare contract terms, and prepare case documentation more efficiently.
  2. 2.
    For students and researchers: Summarize lengthy research papers and extract key insights for literature reviews. Ask specific questions about study methodologies, data results, or theoretical frameworks without reading entire documents. Generate citations and references by asking the AI to identify author information, publication details, and key quotes from academic sources.
  3. 3.
    For businesses: Analyze financial documents to extract budget figures, expense categories, and performance metrics. Review employee handbooks to answer policy questions, or examine vendor agreements to understand terms and pricing structures. Teams can collaborate more effectively by asking questions about shared documents and getting consistent, accurate answers across departments.

How to get started with pdfFiller's Ask Documents

Your step-by-step guide to using Ask Document AI chat

  1. 1.
    Create your free pdfFiller account or log in to your existing account at pdffiller.com.
  2. 2.
    Upload your documents using the simple drag-and-drop interface or browse from your device. Supported formats include PDF, DOC, DOCX, XLS, XLSX, PPT, and more.
  3. 3.
    Click the AI assistant tool at the top right of the toolbar.
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  4. 4.
    Start asking questions directly within the platform. Type your questions in the AI assistant interface and receive instant, accurate answers from your uploaded files.
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  5. 5.
    You can then edit text, add images, rearrange pages, eSign your document, and more.
  6. 6.
    When finished, click Done to save changes. Download, print, or send your PDF form to your recipients.

Testimonials and success stories

Small business owners report saving 35+ hours monthly by using an AI assistant to quickly extract information from contracts and proposals. Real estate agents use the feature to instantly pull property details from lengthy agreements, while consultants analyze client documents to prepare presentations faster.

One HR manager shared: "I can now answer team member policy questions instantly by asking our handbook directly. What used to take 15 minutes of searching now takes 15 seconds."

Ready to revolutionize your document management?

Stop wasting time manually searching through documents. Join thousands of professionals already using pdfFiller's AI-powered Ask Documents to work smarter and faster.

Start your free 30-day trial today and experience how artificial intelligence can transform your document workflows.

Transform your document management experience with pdfFiller's free plan trial. Beyond Ask Documents, you'll get access to advanced PDF editing, eSignature workflows, unlimited cloud storage, and collaborative tools—all designed to eliminate paperwork hassles and boost your productivity. Discover why 56 million users trust pdfFiller to handle their most important documents securely and efficiently.

Try these PDF tools

Edit PDF
Quickly edit and annotate PDFs online.
Sign
eSign documents from anywhere.
Request signatures
Send a document for eSignature.
Share
Instantly send PDFs for review and editing.
Merge
Combine multiple PDFs into one.
Rearrange
Rearrange pages in a PDF document.
Compress
Compress PDFs to reduce their size.
Convert
Convert PDFs into Word, Excel, JPG, or PPT files and vice versa.
Create from scratch
Start with a blank page.
Edit DOC
Edit Word documents.

How to chat with AI in your documents

Illustration

1. Upload your file

Drag and drop or import a document from your computer or cloud storage, then open it in the editor.
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2. Enter a prompt

Ask the assistant to find information, clarify complex topics and terms, summarize content, and more. Work through documents faster than ever!
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3. Get your document done

With your answers ready, go ahead and complete your document: edit, sign, or share with anyone.
Upload document

Stop searching. Start asking.

Your editing co-pilot

Not sure what a term means or where to find a specific clause to update? Just ask the AI assistant for suggestions and locations to make editing faster.
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Ask before you sign

Got questions about a contract's terms before eSigning? Ask the AI to define legal jargon or summarize your obligations so you can sign with total peace of mind.
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Share with insight

Before sharing a lengthy report, ask the AI for a bulleted list of its key takeaways. You can then give your team a clear overview by including these points when you share the file.
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Collaborate with clarity

Want to add a helpful comment for a colleague? Use the assistant to quickly find supporting data or clarify a complex point, ensuring your annotations drive the collaboration forward.
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Simplify complex processes with the power of AI

Check out common use cases for the AI assistant.
Instant search
Stop hunting for specific names, dates, or figures buried in your documents. Ask the AI assistant to find what you need and get the exact data in seconds.
In-app guidance
Looking for the right pdfFiller tool and how to use it? Ask the assistant for quick, step-by-step instructions without leaving your document.
Content analysis
Don't get stuck on dense paragraphs or confusing jargon. Command the AI to explain complex sections in simple terms or define any key terms you don't know.
Summarization
Get the main points of any document without reading every page. Ask the AI for a concise summary or a bulleted list of key takeaways to understand the core message.

Who needs this?

Explore how professionals across industries handle PDFs using AI.
Healthcare
Real Estate
Legal
Education
Finance
Human Resources
Healthcare

Healthcare

Streamline the creation of patient intake forms, consent documents, and medical history questionnaires with AI. Use AI-powered OCR to digitize and restore scanned medical records, making them editable and easy to store.
  • Patient intake forms
  • Medical history questionnaires
  • Consent and release forms
  • Insurance claims
Real estate

Real Estate

Create property agreements, lease contracts, and disclosure forms with AI to ensure accuracy and professionalism. Let AI detect and assign signature fields to buyers, sellers, and agents, speeding up the signing process and reducing errors in property transactions.
  • Lease agreements
  • Purchase contracts
  • Property disclosure forms
  • Mortgage applications
Education

Education

Generate student enrollment forms, permission slips, and academic reports with AI to reduce administrative workload. Translate educational materials on the fly to support students from different countries and ensure accessibility for everyone.
  • Enrollment forms
  • Permission slips
  • Academic transcripts
  • Research papers
Finance

Finance

Digitize and restore scanned receipts, invoices, and bank statements for seamless record-keeping. Summarize complex financial reports to simplify data analysis and focus on important insights and decision-making.
  • Invoices
  • Tax forms
  • Loan agreements
  • Financial statements
Human resources

Human Resources

Create offer letters, employment contracts, and performance review templates with AI to maintain consistency and professionalism. Let AI detect and assign signature fields to new hires, ensuring a smooth and efficient onboarding process.
  • Offer letters
  • Employment contracts
  • Performance review forms
  • Employee handbooks

More than an AI PDF editor

GDPR
AICPA SOC 2
PCI
HIPAA
CCPA

Complete document management

Create and edit PDFs, collect data and signatures, collaborate, and keep files secure in the cloud. With pdfFiller, you can take care of all your document needs in one place.

Perfect for individuals and teams

Users love pdfFiller because it’s easy to use, versatile, and reasonably priced. For teams, it offers a secure space to collaborate, share, and track documents more efficiently.

Designed with security in mind

pdfFiller ensures compliance with industry standards such as HIPAA, SOC 2 Type II, and PCI DSS by introducing data encryption, signer authentication, and other safeguards.

Enhance your PDF experience with AI superpowers

Try easy-to-use tools for all your document management needs.
Upload your document

pdfFiller scores top ratings on review platforms

Users Most Likely To Recommend - Summer 2025
Grid Leader in Small-Business - Summer 2025
High Performer - Summer 2025
Regional Leader - Summer 2025
please inform people it isnt a free service before they spend hours doing something that may be important and they are required to pay your ransom for printing and saving.
Anonymous Customer
I am not 100% satisfied reason being the… I am not 100% satsfied reason being the whole document is not turning into Word, I want turn the whole document in word edit, retype as a word document and have it resaved it as word document.
Miss Renee
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FAQs

If you can't find what you're looking for, please contact us anytime!
The Ask Documents feature is included with pdfFiller Premium subscriptions. This comprehensive plan includes unlimited cloud storage, advanced PDF editing, eSignature capabilities, and now AI-powered document chat—all in one affordable package.
Yes, your documents and relevant information are completely secure. pdfFiller complies with GDPR, HIPAA, PCI DSS, and other major security standards while maintaining SOC 2 Type II certification. All data is encrypted during transmission and storage, keeping your data secure, and multi-level access controls protect sensitive information.
Absolutely. As a cloud-native platform, pdfFiller works on any device with internet access—desktops, tablets, smartphones, and even Chromebooks. Start a document review on your computer and continue asking questions on your mobile device without interruption.
pdfFiller uses advanced artificial intelligence algorithms to research papers and provide feedback on areas such as grammar, spelling, punctuation, and overall readability. This can save you time and ensure that your documents are error-free before sending them out to clients or colleagues. You can also choose to enable real-time suggestions while typing, giving you instant feedback as you create your document. With pdfFiller's AI-powered document analysis, you can confidently produce professional and polished documents every time.
There are numerous benefits to using the AI Assistant with pdfFiller. First and foremost, it can greatly improve the quality of your written content. The AI Assistant utilizes machine learning algorithms to analyze long documents and research papers and provide suggestions for improvement in terms of grammar, punctuation, spelling, and readability. This not only saves you time but also helps ensure that all your documents are error-free. Another benefit is the convenience factor. With the AI Assistant, you no longer have to rely on external tools or editors to review your work. It's all built into the app, making it a one-stop solution for creating high-quality documents.

Enhance your PDF experience with AI superpowers

Try easy-to-use tools for all your document management needs.
Upload your document