Exchange 2010 SSL New Cert Causing Autodiscover Issues

Hello all,
Recently we attempted to move from a wildcard certificate on our Exchange 2010 single server to a digicert SSL certificate. The process seemed easy enough but we found that Autodiscover Outlook clients were getting: "There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name of the target site" and would prompt for credentials. It would never resolve the credentials and continue to prompt, thus never connecting Outlook.
We ensured the cert SANS included as well as all the other to include POP, and IMAP.
What are we missing the server worked fine with the wildcard cert?
Thank you in advance.

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kryanCAuthor Commented:
Very odd, it appears that the autodiscover URL was never configured when I check in PowerShell. Is this possible since it worked with the wildcard?
MAS (MVE)EE Solution GuideCommented:
May be it worked through SCP for internal/domain users
David Johnson, CD, MVPOwnerCommented:
autodiscover uses many different urls
Within the domain it first checks active directory
CN=<CAS_SERVER>,CN=Autodiscover,CN=Protocols,CN=<CAS_SERVER>,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=<ORG>,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=example,DC=com

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Non domain joined machines do the following:
SRV record query where a DNS query for an SRV record is made. The SRV record should be in the format, resolving to the FQDN of the Autodiscover endpoint. Test your settings.
kryanCAuthor Commented:
Turns out the auto-discover was never fully configured and went unnoticed because they had been using a wildcard cert that allowed two everything.


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