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Autodiscover Issues
Question asked by Mark Thornton - 4/3/2024 at 12:29 PM
Unanswered
I am having issues with autodiscover on a new computer I am setting up. The process of setting up a MAPI account on Outlook 2016 on Windows 11 in my environment seemed successful after I walked away for about 15 minutes. I had to provide credentials multiple time but it does now come up and appears to be connected. However it now is asking if it is ok for autodiscover to make changes to the configuration. Other than upgrading to build 8839 no other changes to the mail server or dns server configurations have occurred. I'm struggling to figure out what isn't working anymore.

I ran the Microsoft Connectivity Analyzer and got the following ugly results:
Testing Outlook connectivity.
The Outlook connectivity test failed.
Test Steps
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for chief@southhaysfire.com.
Testing Autodiscover failed.
Test Steps
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
Test Steps
Attempting to test potential Autodiscover URL https://southhaysfire.com:443/Autodiscover/Autodiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name southhaysfire.com in DNS.
The host name resolved successfully.
Additional Details
Testing TCP port 443 on host southhaysfire.com to ensure it's listening and open.
The specified port is either blocked, not listening, or not producing the expected response.
 Tell me more about this issue and how to resolve it
Additional Details
A network error occurred while communicating with the remote host.
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.southhaysfire.com in DNS.
The host name resolved successfully.
Additional Details
Testing TCP port 443 on host autodiscover.southhaysfire.com to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Test Steps
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
Test Steps

3 Replies

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Oliver Replied
4/3/2024 at 12:45 PM
Hello Mark,

the Microsoft Connectivity Analyser is unfortunately not meaningful for SmarterMail, as SmarterMail creates the certificates with ECDSA signature. Other providers of Exchange alternatives use RSA signature. 

But did not find much interest.

The best thing is to click on the Outlook icon while Outlook is open in the taskbar with the CTRL key pressed and the right mouse button pressed. The item "Test e-mail autoconfiguration" now appears here. You can also use this to test Autodiscover.

Hope this helps a little.

Best Regards
Oliver
0
Mark Thornton Replied
4/3/2024 at 2:01 PM
I was looking for a way to test connectivity prior to having a successful creation of an account in Outlook. 
0
Oliver Replied
4/3/2024 at 2:14 PM
You can also start Outlook without an account or use Outlook on another computer. 
The account to be checked does not have to be set up in Outlook.
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