Arrgghh! I sometimes feel that I am beating my head against a virtual wall. I have a user that wants to use Outlook Anywhere, ie- they don't want to use Outlook Web Access or a VPN. As they put it, "I just want to turn on Outlook and be able to connect." The architecture is an SBS 2003 Server running Exchange 2003. As I understand it, if I am able to use Outlook Web Access, I should have the ports open that I need. I have set up an outlook account on a box outside of the network (Windows 7, Outlook 2007) and have filled in the information required for a proxy server. When I try to connect to Exchange, I keep getting the username (domain\username) and password box popping up. Any ideas? I have been reading the forum about similar issues, but haven't been able to solve this yet. Any ideas?