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Copilot (windows app) cannot accept file uploads or screenshots

Donna D 0 Reputation points
2025-12-05T10:50:22.5+00:00

Starting yesterday, my Windows Copilot displays a tiny error box if I try to upload any file or collect a screenshot. I am able to provide files to the web version and the mobile version. I checked to see if it was updated recently and my last Windows update was in November. My issue started on 12/4. I checked to see if I was missing any updates and I am not. I have rebooted and the issue still persists. I'm using the app that was downloaded from the Microsoft App Store, so I uninstalled and reinstalled the app. After doing that, I'm still getting the error.

Things that are happening:

  1. When I first opened the app after reinstall (and this has happened randomly other times, as well), I get a screen that says "Well, that wasn't supposed to happen. We hit a snag while processing your request. Please try again in a moment." This happened just while opening the app. I hadn't even done anything yet.
  2. If I try to upload a file (I've tried excel, PDF, jpg and png files), I get a tiny box that just says "error". Sometimes a red box will appear at the top of the screen saying the file type is unsupported.
Microsoft Copilot | Windows Copilot | App
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  1. Haien-L 6,925 Reputation points Microsoft External Staff Moderator
    2025-12-05T19:06:23.1633333+00:00

    Dear Donna D

    Thanks for posting your question in the Microsoft Q&A Forum.  

    Thank you for reaching out to us about the difficulties you are experiencing with file uploads and screenshots in the Copilot (Windows app).  This could stem from temporary connectivity hiccups, app cache buildup, or file format checks in the Windows app.

    To help me investigate the state of your content on our side, could you please confirm the following? 

    • Are you using a personal Microsoft account (e.g., @outlook.com, @gmail.com) or a work/school account (Copilot for Microsoft 365)?  
    • Your Copilot subscription type (free, Pro, or Microsoft 365)? 
    • Which browser (e.g., Edge, Chrome) or application desktop? 
    • Any error messages? 
    • What is your Windows version? (Go to "Setting" > "System" > "About") 

    In the meantime, please consider trying my suggestions and keep me updated with anything news from it: 

    • Press the Windows Key + R > type wsreset.exe > press [Enter] 
    • Press Windows + R, type ms-settings:troubleshoot, hit [Enter] > Go to [Other troubleshooters] > Find [Copilot] > [Run] > Follow prompts. 

    Note: Ensure under 50MB; try images (JPG/PNG) first—docs may need Copilot Pro for full support. Note: Avoid protected/sensitive files, as they might block 

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".  

    Note: Please follow the steps in Change your Microsoft Q&A preferences | Microsoft Learn to enable e-mail notifications if you want to receive the related email notification for this thread. 

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