When trying to send mail over VPN, I get this error from Entourage:

An operation on the server timed out. The server may be down, overloaded, or there may be too much net traffic.
Sometimes it works and other times not. All the internal workstations send fine. We have SMTP auth on but just plain and login.
All the other VPN functions work perfectly. Also from ISP's that allow you to use external SMTP I can also get it to work sometimes and then it stops..
What am I doing wrong?

Jeremiah
Many applications cache DNS settings while they're running.
When you connect to your VPN, you probably need a different DNS response because you are on a private LAN. That's probably why it sometimes works with ISPs which allow SMTP, in that case you are probably using the external public address (cached) even though you are connected by VPN.
Try quitting and relaunching Entourage.
If that doesn't work, you could try some more troubleshooting.
Try entering the private/LAN IP of the SMTP server instead of the host name you probably have now.
This is just a test and won't work when you're not on LAN or VPN.
Jeff

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