IT Consultant Everyday Notes

Just some problems/solutions storage

Category Archives: Active Directory

Azure: Azure AD Application Proxy. Kerberos issue

One of my Customers asked about MFA for his on-prem Outlook. I offered several solutions, one of them – publish OWA site via Azure AD Application Proxy and pre-authenticate with Azure AD and MFA.

To be sure the configuration will work I built a Lab and tried to configure SSO for Internal Windows Authentication (IWA).

This configuration requires I configure Kerberos Constrained Delegation (KCD) in Active Directory and configure Delegation in Properties of a machine where I have my Azure AD Proxy Connector installed.

Everything looked easy on paper byt when I tried it in Active Directory Users and Computer MMC I received nice error: “The server is unwilling to proceed the request”


After unsuccessful googling I opened a case with Microsoft – that was a brand new domain, just couple of servers and I definitely expected everything working out of the box.

After couple of days of troubleshooting the only solution MS suggested was using an Active Directory Administrative Center instead of MMC. Even with that the first attempt failed with “Unknown error”. After the Center was restarted we could finally configure the delegation. No root cause found.