Welcome Joseph M
Thank you for the detailed information. I understand how frustrating it is when the files upload successfully but Copilot cannot access their contents.
Before troubleshooting further, could you clarify whether you are signed in with a personal Microsoft account or a work or school account provided by an organization? Also, are you using the consumer Copilot experience or Microsoft 365 Copilot?
In meantime, please try the following steps:
- Start a completely new Copilot chat session instead of reusing the current conversation.
- Upload a single small test file directly from your device, such as a simple PDF, XLSX, or CSV file under 10 MB.
- After the upload completes, ask a basic question such as: "Please summarize this file."
- If the test file works, re-upload one of the original files and test it in the same new conversation.
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