Outlook 2007 SSL error messages on Startup when connecting to a single server running all the roles
I’ve done a couple of installs recently for small customers where they haven’t been big enough to warrant having multiple Exchange servers so we have put the mailbox, HUB Transport and Client Access all on the same box. To get OWA and active sync working we put an SSL certificate on these boxes. This gave us an error message when starting Outlook due to the fact that the SSL certificate is bound to the External name of the server and Outlook 2007 connects to the Internal name giving a mismatch error.
Using one of the new SSL certificates is usually the way to go now, where you can assign multiple names to a single SSL certificate to get round this issue, but in these cases I had to re-use existing SSL certificates and couldn’t get a new one.
This article helps you get round that.
http://www.proexchange.be/modules.php?name=News&file=article&sid=403