I have very annoying logon request after run Outlook 2007 into Exchange 2007 SP1 on Windows 2008 when running Outlook Anywhere. This logon prompts me to login into mailbox server (why MBOX, not CAS?!). I have multi-role: CCR mailbox cluster and CASHUB with NLB. I'm using NTLM auth for OA.
The strange thing is when I configured succesfuly Outlook with normal MAPI connection, then changed to OUtlook Anywhere and forced to use it - then everything works fine and Outlook work in RPC over HTTPS...but after reboot PC the logon prompt starts again.
Outlook Anywhere doesn't work correctly when I'm trying configure new profile with Autodiscover. It takes a very lont time (but succesfully) and after that it prompts me for logon into MBOX server.