I have this issues with various clients I have setup SBS with (2008 or 2011).
The problem is this...most of the time (but not all of the time), clients on the local network cannot resolve remote.xxx.com to the local internal IP of the server. It resolves to the public IP instead of the private. The problem is that our firewall (Sonicwalls) don't handle it well and webmail and Outlook setup for Outlook Anywhere don't work.
I have setup a Forward Lookup Zone in DNS on the server for remote.xxx.com and assigned a A record with the internal IP. I can ping remote.xxx.com on the server and it resolves to the local LAN IP. Clients, though, frequently resolve to the external IP, even though their primary DNS is set to the SBS server!
What can I do to ensure that clients (notebooks on office WIFI for instance) resolve to the local private IP when in the office, and the external public IP when outside the office???
Thanks.