CoPilot Can't Remember the Documents I Upload

Copilot is treating each upload as if it’s new because of how file upload and limits work, and possibly because of which Copilot experience is being used.

Key points and checks:

1. Confirm supported file types and sizes
   • For consumer Microsoft Copilot (web/mobile): PDFs are supported, but each file must be ≤ 50 MB and you can upload up to 20 files per conversation.
   • If a file is too large or in an unsupported format, Copilot may keep asking to upload again.
   • If using Microsoft 365 Copilot Chat (work account), standard file upload limits apply and files are stored in OneDrive for Business.
2. Make sure files are actually attached in the chat
   • Use the + / Add images or files button (or paperclip in Edge) and confirm each PDF appears as an attachment in the chat window before sending the prompt.
   • After the files appear as attachments, send a prompt that explicitly references them (for example, “Using the PDFs I just uploaded, identify trends in X”).
3. Stay in the same conversation
   • Uploaded files are scoped to the current chat session. Starting a new chat or refreshing the page means Copilot no longer has access to the previously uploaded files and will ask for them again.
   • Keep all follow-up questions about those PDFs in the same thread.
4. Watch for daily/usage limits
   • Copilot enforces usage limits (for example, AI credits or daily caps). Repeatedly re-uploading and re-asking can consume those quickly, leading to “you’ve reached your limit for the day.”
   • To reduce usage, upload the PDFs once in a single conversation and ask multiple follow-up questions about those same files instead of re-uploading.
5. If using Microsoft 365 Copilot Chat at work
   • Upload via the “(+) Add content” button or drag-and-drop into the chat box.
   • Once uploaded, Copilot Chat can summarize, analyze, and run data analysis/visualizations over those files as long as they remain attached in that conversation.
   • Uploaded files are stored in OneDrive for Business and can be deleted there at any time.
6. If using Copilot in Edge at work
   • Use the paperclip icon or drag-and-drop into the Edge Copilot sidebar.
   • After upload, the file content is treated as if pasted into the chat; follow-up questions should work without re-uploading, as long as the same chat session is used.
7. If issues persist
   • Try a smaller subset of PDFs (for example, 3–5 at a time) and ask for trends across just those.
   • If using Microsoft 365 Copilot for work and the behavior continues across browsers/devices, contact the organization’s admin or support to check for tenant-level restrictions or issues with Copilot features.

References:

• File upload in Microsoft Copilot
• File formats supported by Microsoft 365 Copilot
• Using Microsoft Copilot in Edge at work
• Frequently asked questions about Copilot Chat