Copilot Chat on Windows repeatedly triggers a file‑access permission prompt; Copilot Health does not

Brad Smith 5 Reputation points
2026-09-16T19:02:03.1366667+00:00

Summary of Behavior: Copilot Chat on Windows displays a Windows dialog asking whether to allow access to local files every time a new chat is started. This happens consistently and repeatedly.

Copilot Health does not display this dialog. If Copilot is closed, reopened, and the user goes directly into Copilot Health, the permission prompt does not appear — even when asking questions that require analysis or reasoning.

Copilot on iPhone also does not display any permission prompt.

Repro Steps:

  1. Open Copilot Chat on Windows.

Start a new chat.

Windows shows a dialog asking whether to allow access to local files.

Close Copilot completely.

Reopen Copilot.

Navigate directly to Copilot Health.

Ask a question.

No permission dialog appears.

Use Copilot on iPhone.

No permission dialog appears.

Troubleshooting Attempts (All Unsuccessful):

Toggled Windows “File system access” privacy settings (global and per‑app).

Verified Edge permissions.

Closed and reopened Copilot.

Tested Copilot Health (no prompt).

Tested Copilot on iPhone (no prompt).

Tested multiple chat sessions (prompt appears every time).

Reboot not yet tested, but all other attempts show the behavior is isolated to Copilot Chat.

None of these actions changed the behavior. The permission prompt appears only in Copilot Chat on Windows.

Impact: This behavior is highly disruptive and makes Copilot appear unsafe or intrusive. It undermines user trust, especially for users who rely on Copilot Health. It creates confusion, breaks workflow, and makes Copilot feel unusable. This is likely to push users toward competing AI products that do not exhibit this behavior.Summary of Behavior:

Copilot Chat on Windows displays a Windows dialog asking whether to allow access to local files every time a new chat is started. This happens consistently and repeatedly.

Copilot Health does not display this dialog. If Copilot is closed, reopened, and the user goes directly into Copilot Health, the permission prompt does not appear — even when asking questions that require analysis or reasoning.

Copilot on iPhone also does not display any permission prompt.

Repro Steps:

Open Copilot Chat on Windows.

Start a new chat.

Windows shows a dialog asking whether to allow access to local files.

Close Copilot completely.

Reopen Copilot.

Navigate directly to Copilot Health.

Ask a question.

No permission dialog appears.

Use Copilot on iPhone.

No permission dialog appears.

Troubleshooting Attempts (All Unsuccessful):

Toggled Windows “File system access” privacy settings (global and per‑app).

Verified Edge permissions.

Closed and reopened Copilot.

Tested Copilot Health (no prompt).

Tested Copilot on iPhone (no prompt).

Tested multiple chat sessions (prompt appears every time).

Reboot not yet tested, but all other attempts show the behavior is isolated to Copilot Chat.

None of these actions changed the behavior. The permission prompt appears only in Copilot Chat on Windows.

Impact: This behavior is highly disruptive and makes Copilot appear unsafe or intrusive. It undermines user trust, especially for users who rely on Copilot Health. It creates confusion, breaks workflow, and makes Copilot feel unusable. This is likely to push users toward competing AI products that do not exhibit this behavior.

Microsoft Copilot | Windows Copilot | App

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