So I have a Windows XP Virtual Machine (within OSX), running Office 2010, and using Outlook 2010 to connect to my new Exchange 2010 server over Outlook Anywhere.
When I first setup Outlook's mail profile, I successfully connect via Auto-discovery and the mailbox correctly caches on my machine.
Then, for some reason, about a day later, my Outlook 2010 sits trying to connect and simply wont - Constantly asking for my password, like it was wrong (but it isn't).
To get it going again, I have to delete the Outlook 2010 Profile, and recreating it - Rinse and repeat every day for the last 4 days so far, so I'm worried other users have the same problem, as we've just upgraded them to Office 2010 as well (It's the weekend so I can't check with them yet), but regardless - I have this crazy problem.
Everything is perfect with the Exchange 2010 server, I don't have any problems with Outlook 2011 for Mac, iPhone Sync, Outlook Web App - They all connect and remain connected perfectly.