Windows Security – Select a Certificate window opens when connecting to an Exchange IIS Virtual Directory

Scenario: You notice that when you attempt to connect to a Exchange Servers virtual directory, such as https://<my_exchange_namespace>/autodiscover/autodiscover.xml ,
you receive a prompt similar to this:

Select a Certificate
Site <domain name or server name> needs your credentials>
<Certificates listed to select>

In our case, Autodiscover was not working correctly via DNS lookups, but the SCP record was pulling settings just fine.

Cause: Check the SSL Settings on the Virtual Directory in the Internet Information Services (IIS) Manager. Example: Expand Server –> Sites –> Default Web Site –> select Autodiscover (or whatever the virtual directory giving you an issue is). In the IIS area, select SSL Settings and make sure your certificate is setup to Ignore. You may want to go a hierarchical level higher and make sure the SSL settings are set correctly on the Default Web Site.