Outlook keeps prompting for password, account fails
Nine times out of ten autodiscover is the culprit. A stale DNS record or a hijack domain points Outlook at the wrong server.
Try this first
- 1Test via the Microsoft Remote Connectivity Analyzer (testconnectivity.microsoft.com). It tells you per step where autodiscover stalls.
- 2Check DNS at your registrar: is there an autodiscover CNAME pointing at an old provider? For M365 it should be autodiscover.outlook.com.
- 3Group policy or registry can hold ExcludeHttpsAutoDiscoverDomain set wrong. For M365 it should be 1.
- 4Recreate the Outlook profile via Control Panel, Mail. A half-populated cache rarely heals on its own.
When to bring us in
If you run hybrid Exchange or just migrated from another provider, autodiscover is a minefield. We have scripted tests for this, pull us in around the DNS cutover.
See also
- Outlook crashes or freezes on large attachmentsUsually the mailbox cache is the culprit, not Outlook itself. Shrinking or relocating usually helps within ten minutes.
- Teams: they cannot hear me, or I hear nothingIn our experience Teams usually picked the wrong audio device after a Windows update or a new headset.
- OneDrive has stopped syncingThe cloud icon is grey or has a warning. Locally changed files are not showing up for colleagues.
None of the above fits?
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