Exchange Server Through VPN

[EnemyAce]

Just wondering if anyone has seen this issue, or can point out something I'm missing.

I have a remote user in the office that I've recently migrated from Outlook 2000 to Outlook 2003. Formerly, he was using a pst file and connecting to our Exchange server via POP3/SMTP over a VPN connection. This setup worked fine.

During the upgrade, I decided move his mail onto the Server and use cached Exchange mode to store an offline copy of his mail via an .ost on his laptop. I felt this provided a little more redundancy, since the Exchange server IStore is backed up each night.

The problem is, when he now VPN's into the office, he cannot connect to the Exchange Server. I've narrowed it down to the following; after establishing his VPN connection, any attempts to ping the mailserver result in obtaining the external, public, IP rather than the internal private IP. I've played around with the 'use default gateway' checkbox in his VPN TCP/IP properties but to no avail.

The strange thing is, his machine is Windows 2K, when I compare it to my own laptop, which is Windows XP, it works fine, and all VPN settings, Office Versions are identical! The only difference is the O/S, is that my problem?

Dave

 

[Serbtastic]

Check your DNS/WINS settings on the user's machine.

 

[EnemyAce]

I have, he's configured to automatically receive the proper WINS/DNS server and IP when he VPN's in, which he does.

Once he's connected, he can ping any internal machine and receive the correct private IP, any machine except the mail server, which returns the external public IP. This is pinging with either the NetBios name or FQDN.

It's as if something is being cached somewhere. I tried an ipconfig /flushdns, but this had no effect.

 

[Serbtastic]

Check your local hosts and lmhosts files for reference to the mail server name/IP.

 

[donwaters]

I have been looking on Microsoft site for an example of what that Mail Server line should like in HOSTS and LMHOSTS. Can you give an example?

 

[Serbtastic]

Hosts file should look like:

x.y.z.w hostname hostname.domain.com

LMHOSTS file should look like:

x.y.z.w hostname #PRE

The #PRE tag preloads the entry into the local name table.