MS Exchange via Outlook Over VPN

For some reason a client’s outlook was having issues connecting to Exchange via the VPN connection. Turns out it was a simple DNS resolution problem, setting a static entry via the hosts file solved it.

Outlook 2003, upon opening would sit there “Trying to Connect” (to the Exchange on SBS 2003) for ages, if you left it long enough eventually it would connect. This had only been happening the last week, prior it never did this.

I made sure the VPN connection was connected and I could ping the Exchange host (via IP, not name) and I could. Then as I was sitting there flicking the setting for Cached Exchange Mode on and off and restarting Outlook, it dawned on me “hang on, when I type the IP address in during setup, Outlook resolves the IP to the servers DNS entry”. I pinged the DNS name and it didn’t work. Adding the static entry to the hosts file, flushing the resolver cache and then restarting Outlook, presto connected!

Talk about a pain, be good if Outlook could give some sort of feedback rather then “Trying to Connect” and then “Error”. The whole issue is probably the fact that I setup DNS resolution to OpenDNS and it doesn’t do “nx domain” responses unless you set that up….