Hi guys,

Would appreciate any advise given to the following issue:

I've installed and configured Exchange 2013 Std for a new organization, as a stand alone server.

Very small scale, with all pre and post configuration done. I'm in a testing phase by checking mail flow and set up of accounts from the clients side in outlook, all with success. ( OWA also in working 100%).

Today, when I needed to create their profiles in outlook, authentication takes place until the final step > logging on to mail server, where it fails. I've ruled out any authentication issue that might be the cause.

Regarding certificates, I'm using the self signed certificates exchange creates by default until I receive a 3rd party cert. This also, I believe is still in tact, with no changes made since the initial configuration.

Any ideas as to why there would be a problem logging on to the server all of a sudden?

Note, that accessing their accounts through OWA works perfectly. Just outlook itself where the error occurs.

Thanks in advance

• Edited by Techn101 15 hours 25 minutes ago

As long as the self signed certificate matches the hostname you are using to access the exchange server, then all you need to do is to install the cert on the workstation you're using to test with under the "Local Computer\Trusted Root Certification Authorities".

The easiest way to do this is to browse to the servers OWA URL using IE. When you get the certificate warning, continue to the website. Now click on "Certificate error" in the address bar and choose "view certificates".  Now click "install certificates" and choose "local machine".  Now choose "Place all certificates in the following store" and click browse. Choose "Trusted root certification authorities" and click "OK", "Next" and then "Finish".

Close IE out and then open IE and go to the same URL.  You shouldn't get the cert error now.  If you get no cert error, then you should be good to go.

I would also suggest downloading the test client from testexchangeconnectivity.com. That will help identify any other configuration issues you might have.

Thanks for the feedback Corey

I've installed the certificate as you've described above, but something still off with regards to the users connecting to the mail server.

Scenario : Within "Mail(32-bit) when creating a new profile, for the sake of this test I want to see if it picks the accounts up without editing advanced options ( specifying the mail server etc.). So I only specify the email address and the password, which in theory should resolve and connect ( as it has before ).

During this process it does the following:

* Establishing network connection ( which is correct and checked with the green mark )

*Searching for email address settings ( which at this point prompts the pop-up of the certificate and asks for authentication, once given also correct and checked with green mark )

* Logging on to the mail server ( at this point it asks for authentication again, once given, fails and states exchange must be online or connected )

Could this still point to certificate issues, or more AD orientated?

Thanks in advance

if you are still seeing the certificate warning then the self signed certificate doesn't have the matching URL that outlook is using to connect to the server.

I would install the test client from testexchangeconnectivity.com and check with that tool.  Is your Outlook/office up to date with patches?

For testing you might want to create a new self signed exchange cert with all your configured host/domain names in it.