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I've downloaded the most recent Turnkey Linux OpenVPN appliance, set it up as a gateway, created a profile, and can successfully connect to my remote network. Everything is extremely vanilla - I didn't modify the appliance beyond the initial wizard. However, I cannot SSH to any of the systems behind the VPN once I have connected to the VPN. Strangely, I can do all of this:

  • I can ping all of the servers behind the VPN, so they are reachable
  • I can telnet to the systems behind the VPN on port 22, so the port isn't blocked
  • I can reach web resources on systems behind the VPN such as:
    • The Webmin and Shell-in-a-Box services running on the OpenVPN server itself
    • Web pages hosted on a Wordpress system

I just can't SSH to any of the servers behind the VPN once I'm connected. Any ideas?

Arthur Sommers
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  • What is the output of `ssh -v`? – AlexD Dec 22 '21 at 04:00
  • I feel extremely stupid. I've been trying to connect when tethered to my Android phone (I'm on the road for Christmas), and when I reached a hotel, everything worked. It turns out that in the "Hotspot" settings on Android, there's an option for "Allow clients to use VPNs." As soon as I toggled that, I could connect and SSH to systems without issue. Thanks for your help, @AlexD! – Arthur Sommers Dec 22 '21 at 04:46
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    @ArthurSommers you can convert your comment to answer and mark it as solution. – NStorm Dec 22 '21 at 06:09

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