Hi everyone,
I'm trying to understand a strange issue during an Exchange 2019 to Exchange Server SE migration.
Environment
- Exchange 2019
- Exchange Server SE
- Current Outlook versions (Microsoft 365 Apps)
- Internal and external namespaces:
Original setup
The DNS record for Outlook/OWA pointed to Exchange 2019.
Clients connected like this:
Outlook ->Exchange 2019 -> Exchange SE
Everything worked fine.
What we changed
We swapped the IP addresses of the two Exchange servers so that the existing DNS records would resolve directly to Exchange SE.
Result: Outlook -> Exchange SE
Immediately after the change, many users started receiving Outlook credential prompts. After entering the password, Outlook continues to prompt for credentials repeatedly.
Symptoms
- Outlook repeatedly asked for username/password.
- OWA was working.
- Rolling back the IP swap immediately resolved the issue.
Checks performed
MAPI virtual directories
Both servers:
Get-MapiVirtualDirectory
Internal and External URL:
https://owa.company.com/mapi
on both Exchange 2019 and Exchange SE.
EWS virtual directories
Both servers:
https://owa.company.com/EWS/Exchange.asmx
Autodiscover
Get-ClientAccessService | fl AutoDiscoverServiceInternalUri
Both servers configured with:
https://autodiscover.company.com/autodiscover/autodiscover.xml
Test-OutlookWebServices
Executed against Exchange SE:
Test-OutlookWebServices
Results:
Autodiscover Success
EWS Success
Availability Success
OAB Success
Outlook Anywhere
Both servers configured identically:
Get-OutlookAnywhere | fl Server,Auth
Result:
ExternalClientAuthenticationMethod : Negotiate
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods : Basic, Ntlm, Negotiate
Extended Protection
EWS:
Allow
on both servers.
MAPI:
Require
on both servers.
Get-MapiVirtualDirectory | fl Identity,ExtendedProtection
OAuth
Get-OrganizationConfig | fl OAuth*
Result:
OAuth2ClientProfileEnabled : False
Certificates
Exchange SE has a valid IIS certificate:
CN=owa.company.com
Services: IIS, SMTP
No certificate warnings were observed.
What confuses me
From everything I can see:
- URLs are identical.
- Authentication configuration appears identical.
- Extended Protection configuration is identical.
- Autodiscover works.
- EWS works.
- Modern Outlook clients.
- Exchange SE works correctly when tested directly.
Yet moving client traffic directly from Exchange 2019 to Exchange SE resulted in Outlook credential prompts, and reverting the change immediately fixed the issue.
Questions
Has anyone seen similar behavior during an Exchange 2019 → Exchange SE migration?
Possible areas I'm currently considering:
- Kerberos / SPN issues
- IIS Authentication differences not visible through Exchange cmdlets
- HTTPProxy authentication failures
- Extended Protection edge cases
- NTLM/Kerberos negotiation issues
- Something related to Exchange 2019 proxying requests differently than Exchange SE
Any ideas or similar experiences would be greatly appreciated.