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Hi Colin Shelton,
Thank you for posting your question in the Microsoft Q&A forum.
From your description, you mentioned "keychain", it seems that you are using a Mac device, is that correct?
To help narrow down the troubleshooting path, could you please share:
- The macOS version
- The Outlook for Mac build (e.g., New Outlook version 16.xx or Classic Outlook version 16.xx)?
In the meantime, based on your scenario, these Microsoft articles provide the most relevant guidance you can review and consider trying:
- Office for Mac repeatedly requesting keychain access: https://support.microsoft.com/en-us/office/office-for-mac-repeatedly-requesting-keychain-access-ced5a09c-3099-47cb-9190-e961bf63e240
- Outlook repeatedly prompts for authentication (Keychain cleanup): https://learn.microsoft.com/en-us/troubleshoot/outlook/sign-in/repeated-prompts-authentication#workaround
I hope the above suggestions are helpful!
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