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I have a blog post on Outlook Certificate Errors which applies to Outlook 2007, Outlook 2010, and Outlook 2013. That blog post describes an incorrect certificate on Exchange itself.
For example, you make a connection to Exchange and your Internal URLs, External URLs, and Autodiscover Service Internal URI FQDN is not defined on the certificate.
Therefore, you must update the Internal URLs, External URLs, and Autodiscover Service Internal URI to match the certificate FQDN. This issue is that when you are trying to make a connection to Autodiscover via https://autodiscover.domain.com, the Outlook client does not successfully make a connection to it and you get a certificate error.
The certificate you see pop up in Outlook during the error isn’t even the certificate that is located on Exchange.
The certificate error that pops up shows you that it is finding the certificate on your company’s public website. Why the error and why is it showing the company’s public website’s certificate.
Well first, let’s explore a little on the steps External Autodiscover goes through in order to find Exchange.
The Autodiscover service is a mechanism that can do several things.
When you first launch your Outlook client (Outlook 2007 or above required for Autodiscover access), it will search Active Directory for a Service Connection Point (SCP) record.
So please be sure to update all Internal URLs, External URLs, and the Autodiscover Service Internal URI to use an FQDN other than the server FQDN and other than the Net BIOS names of the servers.So an example of how this works for domain joined clients who have access to Active Directory is included on the Autodiscover Whitepaper: A domain joined Outlook client (again, only Outlook 2007 or above clients use Autodiscover) will find this SCP record which will return the Autodiscover Internal Service URI you specify with Set-Client Access Server.Again, don’t forget that it’ll get a list of all SCPs for all CAS servers in your environment and use one at random.If you have slow links or just want to force Outlook clients to use a CAS in their own site, check out my article here.