Users can not send or receive while connected thru VPN

When any of my users travel, they are unable to send or receive any e-mail if they are connected to the office thru the VPN server. Off of VPN they can receive e-mail but they can only send if I white list their IP in my relay. This occurs with different POP3 and IMAP clients. Even when I am connected to webmail, if I am on the VPN I am unable to send messages.

The VPN is simple PPTP setup on our offices gateway router. I have no other issues with VPN other than e-mail. Everything else reacts just as if I were in the office. Both the firewall and the server are set to allow POP3,IMAP, and SMTP, to and from any address.

I have someone out of the office right now and they are getting the following error

connection to the server has failed. Account: 'mail.meteorgames.com', Server: 'mail2.meteorgames.com', Protocol: SMTP, Port: 25, Secure(SSL): No, Socket Error: 10061, Error Number: 0x800CCC0E

Any help would be appreciated,
Chris

XSERVE, Mac OS X (10.5.2)

Posted on May 8, 2009 2:42 PM

Reply
2 replies

May 9, 2009 3:04 PM in response to cbuskirk

This isn't likely a failure of the mail server, more one of DNS.

Does your VPN server hand out an internal-based DNS server that is aware of the internal address of your server?

That is required so that the VPN client changes the DNS settings on the remote machine and tells it to use the internal DNS server for all lookups. Since that DNS server knows the internal/private address of your mail server the mail flows over the VPN and to the server.

The error message you're getting implies that's the problem, more than one of the mail server (e.g. it implies you're not getting a connection at all, rather than getting a connection that's just blocked by the server.

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Users can not send or receive while connected thru VPN

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