This one's for Jamie :-) There seems to be a lot of confusion with customers on how Outlook Anywhere works, especially when using a multiple AD-Site's setup.

Imagine the following scenario in the image below: 

And let us further assume that the users mailbox is located in "Site B" and the combined CAS/HT/MBX in "Site B" isn't accessible from the internet. The user tries to access his mailbox via RPC/HTTPS (Outlook Anywhere) on the CAS in "Site A". Oulook Anwhere is not enabled in "Site B"

So how does this work? More...