Can Copilot read uploaded PDFs in a chatbot like ChatGPT does?

Graziano Stefanelli
May 6
3 min read

Yes — but only certain versions of Microsoft Copilot offer a true “drag-and-chat” PDF workflow, and the experience is not yet as uniform or generous as ChatGPT’s. Below is a 2025-level snapshot to help you decide which tool (or combination) makes sense for your document work.

Both ChatGPT and certain versions of Microsoft Copilot now let you upload a PDF and chat with it.

ChatGPT accepts files up to 512 MB, allows multiple documents in one conversation, and offers built-in Python and visualization tools.

Copilot’s PDF chat is limited to Windows, Edge and mobile apps, caps files at 50 MB, handles one document per session, and is still testing full image understanding.

1 Why the answer changed in 2025

Copilot flavours and current PDF status (May 2025)

Copilot on Windows & Edge – PDF upload enabled (50 MB limit); chat over the file inside the sidebar or standalone Windows app.
Copilot mobile (iOS / iPad / Android) – PDF upload enabled; attach a PDF and ask questions.
Copilot macOS app – Upload for text and PDF in gradual rollout.
Copilot Vision (Windows Insider build) – Beta feature that adds screen reading and local file search for .pdf, .docx and others.
Copilot in Word / Excel / Teams (Microsoft 365) – No native PDF chat; requires pasting or converting the PDF to Word.

ChatGPT Plus / Enterprise has offered file uploads since late 2023 and now supports PDFs up to 512 MB (or two million tokens) and up to 80 files every three hours on GPT-4o.

2 Deep dive — Copilot’s PDF workflow

2.1 How it works

Click the paper-clip icon in Copilot (Windows, Edge or mobile).
Select a PDF (50 MB or smaller).
Ask questions such as “Summarise the executive overview” or “List every GAAP citation.”
Follow-up prompts stay aware of the same file.

2.2 Security & retention

Files are stored for up to 30 days and are not used for model training.
Enterprise tenants can disable uploads through admin policy.

2.3 Current limits & gaps

Size ceiling of 50 MB blocks very large reports.
Chat handles only one file at a time (no multi-file reasoning).
Embedded images are understood only in the Vision beta; otherwise Copilot reads text only.

3 Deep dive — ChatGPT’s PDF workflow

Key characteristics

Maximum file size: 512 MB or two million tokens.
Uploads per window: up to 20 files, capped at 80 files every three hours on GPT-4o.
File retention: tied to the chat; files can be deleted manually or expire automatically; Enterprise uploads are excluded from model training.
Visual retrieval: reads charts and images in PDFs on Enterprise plans (added January 2025).
Built-in analysis tools: Python code interpreter, graphing, and SQL-style querying.

Workflow tips

Combine several PDFs in one chat to request cross-document comparisons.
Use Advanced Data Analysis mode for heavy tables or lengthy documents.
Export code or charts directly from the conversation.

4 Side-by-side comparison (May 2025)

True chat over PDF

Copilot: Available on Windows, Edge, mobile, macOS rollout in progress.
ChatGPT: Available on web, macOS, iOS and Android.

Maximum file size

Copilot: 50 MB.
ChatGPT: 512 MB.

Supported file types

Copilot: PDF, DOCX, XLSX, PPTX, images, TXT, CSV, JSON, Markdown.
ChatGPT: Nearly all common text and data formats.

Image understanding

Copilot: Requires Vision beta.
ChatGPT: Included in Enterprise and Education plans.

File retention policy

Copilot: 30 days.
ChatGPT: Stored with the chat; user-controlled deletion.

Multi-file reasoning

Copilot: One file at a time.
ChatGPT: Up to 20 files per GPT.

Pricing snapshot

Copilot: Free on Windows/Edge/mobile or included with a Microsoft 365 licence.
ChatGPT: Free tier (three uploads a day) or paid Plus / Enterprise plans.

5 Practical scenarios

Quick five-page brochure summary – Use Copilot in Edge for an instant sidebar overview without a subscription.
Analyse a 100 MB annual report with charts – Use ChatGPT Plus for its higher size allowance and image reading.
Ask about a PDF viewed on your phone – Share to Copilot on iOS or Android.
Bulk-compare ten invoices – Use ChatGPT for multi-file conversation and code-based extraction.
Strict on-premises work document – Convert PDF to Word and use Microsoft 365 Copilot so the file never leaves your tenant.

6 Getting the most out of each tool

Copilot tips

Compress or split documents that exceed 50 MB.
Use follow-up prompts such as “next section” or “explain the graph on page 7” to keep context.
Watch the Vision rollout for richer, image-aware answers.

ChatGPT tips

Select GPT-4o for the highest upload caps and fastest responses.
For finance documents, request: “Extract every footnote table and generate a bar chart of revenue.”
Remember the free tier’s three-upload daily limit.