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Sudden IIS issue with SmarterMail / Server 2012 R2
Problem reported by Paul Blank - 7/18/2025 at 9:38 AM
Submitted
IIS Site (SmarterMail) suddenly began asking for authentication or not responding, with error. This is quite sudden. It was working fine until it did not. And an SSL check comes out clean as can be.

Chrome:

But sometimes I "Cancel" this and it works fine.

And sometimes I get a No Certificate Found error.

Firefox:


And SSL checks (https://www.sslshopper.com/ssl-checker.html and others) come back clean.

Any ideas?
0
Paul Blank Replied
7/18/2025 at 10:21 AM

It's looking more like a corruption somewhere in the cert chain. Opened the firewall to an HTTP port and set that port in IIS and SM (not 80) and it's working immediately.

Going to re-key the cert.
0
Paul Blank Replied
7/18/2025 at 12:19 PM
Rekeyed cert - This did not work. Still same errors. Looking for suggestions.
1
Have you tested your autodiscovery?
0
Merle Wait Replied
8/4/2025 at 7:43 AM
Was curious to see how this was resolved?
0
Tony Scholz Replied
8/5/2025 at 12:52 PM
Employee Post
@Paul, 

Are you still seeing an issue with your certificates? 
Tony Scholz System/Network Administrator SmarterTools Inc. www.smartertools.com
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