lick the Edit menu, point to New, and then click String Value.Type the name of the HTTPS server to which Auto Discover can be redirected without prompting for confirmation from the user, and then press ENTER.Outlook will do Autodiscover in the background to ensure that the settings are correct. There is no need to use SRV or HTTP redirect, which is the error would tend to suggest is happening.You can make a change on Exchange and it will be on most of the clients within a few hours. You do NOT get the prompts when you are using A records, only with the other options.It is not (as many Exchange admins believe) a one time thing used for initial configuration.It cannot be ignored because you can configure things manually. Thing is, if you have Autodiscover.in your SSL certificate, then you just need to have an A record in the public DNS pointing to the site.I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing.
As such, while the above posting is a valid answer, it doesn't really deal with the why it is occurring, just the symptoms, particularly if things have appeared to be working correctly. Thanks both, Simon, I'm assuming you are referring to the isp where exchange is, not the isp where the user is?Testing TCP port 443 on host to ensure it's listening and open. The SSL certificate failed one or more certificate validation checks. Test Steps The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server on port 443. Testing the SSL certificate to make sure it's valid. Test Steps The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover. The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate. MYDOMAIN.com, Issuer: SERIALNUMBER=MYSERIALNUMBER, CN=Go Daddy Secure Certification Authority, OU= O="Go Daddy.com, Inc.", L=Scottsdale, S=Arizona, C=US. The Microsoft Connectivity Analyzer wasn't able to obtain the remote SSL certificate. The certificate passed all validation requirements. Additional Details Remote Certificate Subject: CN=mail. this uses comcast business class internet where exchange is so I would be surprised if anything changed, so while not ruling that out I'm thinking your suggestion about config might be the first place to look.I will check to see if there are SRV and HTTP redirects setup.