The administration and maintenance of Microsoft Exchange Server to ensure secure, reliable, and efficient email and collaboration services across an organization.
Hi Chris Melnik
Since you can successfully authenticate but receive a "This page isn't working" (HTTP 500) error immediately after, this indicates a breakdown in communication between the Front End and Back End of the Exchange server.
You can perform the following checks in order:
Check OS and Exchange Compatibility:
You are running Exchange 2019 CU14 on Windows Server 2025. According to the support matrix, older Cumulative Updates of Exchange 2019 may not be fully supported on Windows Server 2025 due to changes in IIS and TLS handling. ̣
Exchange Server supportability matrix | Microsoft Learn
I strongly recommend updating to the latest Cumulative Update or Exchange Server SE, which includes the necessary fixes for Server 2025. The update process often automatically repairs IIS bindings.
Verify IIS Back End Bindings:
- Open IIS Manager > Expand Sites.
- Default Web Site (Front End): Check Bindings (443). This should use your Third-party/Commercial Certificate.
- Exchange Back End: Check Bindings (444). This must use the self-signed certificate named "Microsoft Exchange" and do not use your commercial certificate on the Back End (port 444). If you do, the console will not load properly.
You can refer to:
Fix Failed Exchange Server Updates - Exchange | Microsoft Learn
Assign certificates to Exchange Server services | Microsoft Learn
Check for Expired OAuth Certificate (Event 1003)
If the bindings are correct, the issue is likely an expired internal Auth certificate.
- Check Event Viewer > Windows Logs > Application > Look for Event ID 1003 from source
MSExchange Front End HTTPS Proxy. - If found, you must renew the Exchange Server Auth Certificate.
Can't access OWA/EAC with expired OAuth certificate - Exchange | Microsoft Learn
Restart IIS
After making any of the changes above, run the following in an elevated PowerShell to apply changes:
Restart-Service WAS, W3SVC
I hope this information helps.
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