We've got a Server2008R2 functioning as a terminal server.
Users attempting to open Outlook10 on this server get stuck at "Loading Profile"
Sometimes a username\password field will come up after about 25-30 seconds, filling it out correctly can result in Outlook opening properly 20 seconds later, or a "Server not found, work offline?" window. Sometimes hitting Retry will force Outlook to open.
Sometimes rebooting the server fixes the issue, sometimes it does not.