We have a single name SSL certificate for an external URL (eas7.mydomain.com) which is being used for IIS services - this name is NOT the name of the internal 2007 server. I spent considerable time with MS support to get it to work since people on the inside kept on getting popups. So we ended up adjusting the autodiscoverservice, the webservices virtual directory, the OABVirtualDirectory and the UMVirtualDirectory to point to the name on the URL listed on the SSL. Everything is fine except now one person (upper management of course) wants to skip hooking into the domain through our vpn hardware device (which takes roughly 20 seconds). So he is using a setting on Outlook connections which points to the https URL of the SSL certificate. Every few weeks or so he gets a pop up saying NO - YOU MUST POINT TO THE URL OF SERVERNAME.MYDOMAIN.COM, which does not work since the URL on the outside point to EAS7.mydomain.com. So he is aggravated that he needs to reset it. At the time it was expensive to get a multiple name SSL cert (godaddy.com has a 5 name cert for $90 now) and I am not sure if getting a multiple name cert will resolve the issue or if it will what format should it include so that outlook doesn't have the popups - is there a specific format for the autodiscover service. Or is there some setting on the exchange server that might resolve the issue.

Without a SAN SSL certificate, that means you aren't securing autodiscover.example.com. AUtodiscover tries a number of URLs by default - including example.com/autodiscover, autodiscover.example.com and an SRV record. If the URLs resolve then you can get some odd results. (example.com is the domain after the @ sign in the email address). You should also check the URL for the Outlook Anywhere host, as that will be in autodiscover as well. A single name certificate can kind of work, as long as your external DNS provider supports SRV records and you ensure that there is no SSL certificate on the root of the domain and autodiscover.example.com doesn't resolve. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources