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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.

Sendmail: Using TLS for authentication

Symptoms

You have a laptop or other mobile device running Debian. You have your own Sendmail server, also running Debian. You want to send email from your laptop, but your Sendmail server does not accept your emails if you are not on your local network.

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by Dr. Radut