Outlook Keeps Asking for Password? Check These 5 Things on the Exchange Side

If you’ve ever heard this from a user:
“I keep typing my password in Outlook, but it just keeps asking again!”
Then you know what we’re talking about.

This issue is very common, especially in hybrid environments or after migrations. You might troubleshoot Outlook all day—but the actual issue often lives on the Exchange side.

Where to Look?

1. Autodiscover DNS Record

Outlook needs autodiscover to pull server settings. If the DNS record is wrong, it can’t connect. Check if autodiscover.domain.com is correctly routed and matches both internal and external DNS.

2. Modern Authentication (OAuth)

Is Modern Auth enabled? Conflicts between legacy Exchange and Azure can break login. Check EnableADAL in registry, and verify app permissions in Azure AD.

3. Outlook Profile Corruption

Sometimes the user profile is just broken. Try creating a new Outlook profile and test.

4. Credential Cache Issues

Windows Credential Manager might store outdated entries. Clear Office-related entries via Control Panel > Credential Manager.

5. Exchange Virtual Directory Configuration

Misconfigured autodiscover or EWS directories on Exchange can prevent authentication.

Get-AutodiscoverVirtualDirectory | FL Identity,InternalUrl,ExternalUrl

Real-Life Case

Once, a client had this exact issue. Turned out the CNAME record for autodiscover was missing. 2 hours of stress could’ve been 2 minutes—if we had looked in the right place first.

Final Thoughts

Instead of fighting Outlook, step back and inspect the whole setup. Exchange, DNS, Azure, authentication—it’s all one big puzzle.

What’s the trickiest Outlook login issue you’ve fixed? Let’s build a solution pool together.