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PaddyY1
Dec 26, 2025Occasional Reader
Teams drag-and-drop upload fails only from macOS screenshot thumbnail / markup window
I’m encountering a reproducible issue with Microsoft Teams file uploads that appears to be specific to the drag-and-drop source on macOS.
Steps to reproduce
- On macOS, take a screenshot using:
- Cmd + Shift + 4 or Cmd + Shift + 5
- When the floating screenshot thumbnail / markup window appears (bottom-right of screen), do not save the file manually
- Drag the screenshot directly from the floating thumbnail or markup window
- Drop it into the Teams message compose box in:
- a 1:1 chat, or
- a group chat
Result
- Upload gets stuck on Uploading
Environment
- macOS
- Teams Web (Chrome)
- Teams macOS desktop app
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