Now to find why NTLM didn’t work ? Turn out there was a setting in the default domain policy (GPO) denying all NTLM connection on all the computers in the domain. Software\policies\microsoft\office\16.0\outlook\security Now outlook can connect with NTLM or Kerberos to the exchange server, so I forced the workstation connecting with NTLM only -> that didn’t work ! but when I set the Kerberos as default the outlook connect in a flash, this are the registry setting for outlook 2016 : At that point I figured that the authentication mechanism wasn’t working and it hand nothing to do with certificate or exchange server health. There were no eventID in any log regarding any thing about certificate issue. : The remote certificate is invalid according to the validation procedure. To check outlook and I got this weird error complaining about certificate missmatch issue :Įrror : : The underlying connection was closed: Could not establish trust relationship for the SSL/TLS secure channel.
The test pass without any hard issue, clients from outside the organization were connecting without any problem and fast ! But from the domain network itself workstation couldn’t connect with outlook, OWA was working fine any were, so I ran: Get - ClientAccessServer | Test - OutlookWebServices - Identity - MailboxCredential ( Get - Credential ) | fl in order to check outlook connectivity i used Microsoft Connectivity analyzer : I had a weird case of organization suffering from outlook that couldn’t connect to the exchange, the security window was popping all the time regardless the credential input.
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