Hi All,

Thank you for looking into this!

We have a strange problem; Once Laptop is connected to VPN (Checkpoint), Outlook 2010 shows "Trying to connect". 

I go to Connection Status Window and see one CAS Server listing but "Interface" column shows nothing. It is blank.

After doing Ipconfig /all on the PC, I can see VPN adapter is listing first, but I don't see Default Gateway for VPN adapter. I can see Default Gateway assigned to WiFi Adapter. Could that be an issue? I can ping domain name successfully. I can ping CAS Server also. Nslookup resolves CAS to an IP Address.

It works without any issues once Laptop is connected to LAN.

Your help is greatly appreciated!

Thanks,

Nratawa

check if this helps:

http://serverfault.com/questions/352974/force-outlook-2007-2010-to-use-ip-address-for-exchange-server-instead-of-host-na

Outlook is connected over the internet, and when VPN takes over, Outlook cannot connect to the outside address. This is related to firewall setup, but is quite normal I think. Instead of adding more complicated firewall rules, allow split tunneling for your VPN connection, or have a DNS record in your INSIDE/VPN network that resolves the CAS public fqdn to its inside address.

I can resolve CAS to an IP from client machine after connecting to VPN. I can also see Exchange Connection Status window showing MAIL, Directory and Proxy names in there. It shows "Connecting" in Exchange Connection Status window but then suddenly list disappears.