Question : Netpilot through a VPN


I have a client who has a Netpilot solution (a product I have no knowledge of) that they use as their e-mail/internet monitoring/firewall solution.  I have a client with a laptop that can access his email fine when he is in the office, but when he gets home and activates his OpenVPN client he gets smtp errors and his mail doesn't send.  It does receive the e-mails though.

The settings in outlook are setup as a POP3 account with the POP3 address being that of the local Netpilot box and the SMTP (which is failing) is the address When on the VPN you change the SMTP address to the local IP of the Netpilot send e-mails fine, but doesn't work when back at the office off the VPN when trying to e-mail external clients.

When connected over the VPN the internet is still available.

The error is 550 SMTP authentication error



Answer : Netpilot through a VPN

Got it works finally.... I should adjust my mind to investigate from an end user perspective...

Under Control Panel, go to Network and Sharing Centre -> Change Adapter Settings -> Choose your LAN connection interface and your OpenVPN TAP interface -> Right Click choose Bridge the connection -> A MAC bridge miniport is created automatically -> Copy the TCP/IP setting from original LAN connection interface settings to the TAP interface... and here you go.

And of course, you should have a proper server.ovpn file for your Windows.

Check this out for your reference,

Thanks all for the replies :)
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