I recently moved a client from a hosted service to Exchange 2010. Everything works great except for an issue with Outlook anywhere. I have several laptop users that need to use Outlook both in and out of the office. If I configure Outlook anywhere when they are in the office it works fine, but it will stop working as soon as they leave. Outlook comes up and prompts for credentials and then just says disconnected.
What's really got me confused though is that if I recreate the users Outlook profile when he is off site Outlook will connect right up and start downloading mail. It will continue to work until the user goes to the office and connects to Exchange. After that it will not work again when he is off site.
I have 4 different users that are all experiencing this problem.