Question : Outlook Disconnected to Exchange Over VPN

Server running SBS 2003, Exchange 2003
Laptop running Windows 7 Professional, Outlook 2007

I use my laptop to connect to the server at work from both the Office and at home. At work I connect directly to the network via ethernet and from home via VPN. I logon to my laptop the same way both places, i.e. \\network\userid.

When I connect at work, I never have problems getting to Exchange and it connects every time. However, at home, after I connect over the VPN and then open Outlook, MOST of the time it comes up Disconnected and then won't connect after the "Trying to Connect..." message comes up.

I've setup the profile to prompt me for the connection state in Outlook and have tried starting it both in Offline mode as well as Connect, but that hasn't helped. What's strange is that sometimes during a session, when I perform some activity on the server (like synching offline files, or remote desktop to the server), if I retry connecting to Exchange, I am able to connect to Exchange and everything updates just fine. I can find no common pattern to the activities I perform, nor does this work every time.

This has been going on for what seems like forever and I've just lived with it, but it would sure be nice to finally figure it out so that I could get connected whenever I want. Any help would be greatly appreciated.

Answer : Outlook Disconnected to Exchange Over VPN

Try and configure a secondary address on the OWA server and bind it to the interface (192.168.6.40; if available), remove/update the NAT for 203.65.45.8 192.168.6.8 to point to the new IP of the .40

I am not familiar with the firewall that you do have; I am thinking the static NATs are having issues. What possible could be happening is that the connection (Initial SYN Packet) arrives at the firewall (203.65.45.8), then gets translated, sent to the server,  server receives the SYN, the server then sends a SYN ACK back, but the firewall already has a static NAT for 203.65.45.7 192.168.6.8 so as there is no stateful connection, in the NAT table, and the firewall is sending back the RST, ACK. However, the firewall has a stateful connection for the 203.65.45.8 192.168.6.8, maybe it is using the first static NAT in the table it finds is the only thing that I can think of.

Billy