Azure AD Connect : Connect to Azure AD: Authentication request was cancelled. Why? Nothing in Event Logs.

Grego2020 21 Reputation points

While setting up a second Azure AD Connect server, something is cancelling my authentication to Azure AD via DUO MFA after entering account username of Azure AD global administrator. I should get a pop up window from DUO to enter username and password, but instead I get a window that appears to open and closes and a message “Authentication request was cancelled. Learn More” in the AAD Connect application. I believe it is a Windows Server 2019 or AADCONNECT issue but am investigating DUO MFA also.

Troubleshooting Azure AD connectivity via logging into, microsoft365 and shows connectivity as does entering an invoke-webrequest -uri in powershell returns a 200 or OK status.

Nothing shows up in the event logs on the server. Windows Firewall being disabled shows no effect.

Azure Active Directory
Azure Active Directory
An Azure enterprise identity service that provides single sign-on and multi-factor authentication.
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  1. Grego2020 21 Reputation points

    I have tried several accounts. One with no MFA associated with it. I tried my account with MFA bypassed in DUO. I tried my username@**** The authentication window pops up for a half second, closes and i get "Authentication request was cancelled".