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VPN woes

Yet another random wifi network to connect to - this time in a small cottage in Slovenia. It actually allows access to internet, allows me to setup a VPN, so all seems well. Except for one little thingie: for some reason, it blocks outgoing SMTP traffic.

Well, no problem, there. I want to mail from my laptop, and it delivers to the mail server on my server. No problem there, if I route the traffic through the VPN, right? Wrong. After setting up the VPN it is still not working.

OpenVPN: Routing content for your connection point


You use a VPN to connect your mobile device, for example your laptop, to your server. All traffic should go through this VPN, as you do not trust random networks you may connect to. This works fine, except when you try to connect to your server through its public IP address. As this is also the IP address that is used as the VPN end point, traffic to it does not go through the VPN but is routed, unencrypted, through the untrusted network.

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by Dr. Radut