Recently I've set up Exchange Server 2016, configured external DNS accrodingly. Server itself works fine, can send and receive emails. OWA is working fine aswell (externally and internally).

Issue is that Autodiscover is not working properly. I can open it externally via https://example.com/autodiscover/autodiscover.xml (it prompts for user and password), but cant set up an account in Outlook.

When testing with MS Connectivity analyzer it returns that it cannot validate certificate, which is fine since I dont have one and as far as Im cocerned it should work without it. What bothers me is this error: The Autodiscover service couldn't be contacted successfully by any method.

What could be the cause and solution to this problem?

  • Can you add a export fro the MS Connectivity Analyzer and remove all sensitive information?
    – BastianW
    Nov 10, 2017 at 10:03

1 Answer 1


The most reason why you got a invalid SSL certificate during auto discover is the following:

  • The ssl certificate you are using is selfsigned and not trusted externally
  • You are doing any http redirections and one from the servers isn´t part from the SSL certificate
  • Your Exchange AutoDiscovery configuration points to the wrong URL (you can check that for example via "Get-WebServicesVirtualDirectory | FL")
  • ...

For more info's / Help we need a dump from the MS Connectivity analyzer.

  • Fixed the certificate errors by generating a correct self-signed certificate in Exchange Admin panel. No errors are reported now in analyzer. Now my problem is that autodiscover itself isnt working. Prompts for domain cridentials whenever im trying to add an account. Anyhow thanks :)
    – Jon
    Nov 10, 2017 at 12:29
  • The best one would be to open a ticket Question here with the remaining issue (and including the info that AutoDiscovery is working general based on the analyzer). By the way if you use the same credentials on the analyzer which aren´t working internally it might be that the configuration in exchange isn´t correct. Means the outlook client is fetching something form the AD rather then the auto discovery. However the best way would be to start a new question i think.
    – BastianW
    Nov 10, 2017 at 13:37

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