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Outlook issue with App Specific Password and iCloud

Phil Walter 30 Reputation points
2025-12-04T08:53:36.97+00:00

I have been using outlook with my iCloud email for years. I have recently been asked to enter my password again and it will not accept my App Specific Password. This is both on a desktop and on my M5 13in iPad Pro.

I have tried the original passwords, creating new passwords and all potential alias to no luck. I think this happened about the same time as the app was updated on my iPad.

I do have this still working on my iPhone and my work laptop. It is only two of the 4 devices that are causing an issue.

I have tried copy and pasting, typing to ensure that no random chars are included and even tried removing the -.

Any other throughts?

Moved from Outlook | Outlook for mobile | Outlook for iOS | For business

Outlook | Outlook for mobile | Outlook for iOS | For home

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  1. Phil Walter 30 Reputation points
    2025-12-04T10:12:12.0933333+00:00

    I managed to resolve the issue by forcing this through an advanced set up, the app-specific password was accepted when entered directly into the Outlook interface and not the Apple Sign-in page.

    This suggests that something has changed in the process that is out of sync with how the process is expected to run.

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