We are having an issue with an SBS 2008 Outlook Anywhere. It seems only one client can connect at a time. As soon as a second client instance of Outlook starts, the 2nd client gets stuck on "Trying to Connect". If the 1st client closes, and then you re-open the 2nd, it connects right up. Both are at the same remote location, so from the SBS perspective, they are both originating from the same client IP.
Any thoughts on how to fix?