Outlook prompting for credentials after migration

Question

Good day all i'm currently experiencing a strange issue with Outlook being prompted for Username and password after migration.

The strange thing is if i use the new SaRA tool - SaRACmd.exe -S OutlookEmailSetupScenario -AcceptEula

It says there are no issues, and it creates a new profile just fine, but if i try to load the old profile it keeps prompting

Secondly, if i use HKEY_CURRENT_USER\Software\Microsoft\Exchange (AlwaysUseMSOAuthForAutoDiscover set to 1), then create a new profile or use the existing one, then it prompts for credentials and connects just fine.

Thirdly if i cancel the Outlook login prompts on the original profile, i'm met with the "Allow this website... " autodiscover message, which if i Allow doesn't do anything and just fails.

The Outlook version is M365 Apps Microsoft 365 MSO (Version 2408 Build 16.0.17928.20336) 64-bit

Windows version 22H2 19045.5371

Its in Classic Outlook Mode

Autodiscover still points to Exchange 2019 CU14

Any ideas? Thanks

Answer 1

Hi @Raymond Brooks ,

Welcome to the Microsoft Q&A platform!

 
This can be caused by the presence of old and new credentials that end up conflicting with each other after migration.

Although the email address and password may be the same, the GUIDs generated may not be the same between different exhcange server versions, which can lead to internal errors.

I suggest you access it via Control Panel - User Accounts - Credential Manager. Delete all credentials under web credentials and windows credentials. After deletion, outlook will prompt for password again, enter it correctly and select “Remember my credentials”.

Until then, to prevent other errors, you can backup your credentials.

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