Accessing Plex via SSH

Server Version#: 1.15.8.1198
Player Version#: 3.102.0

I am running Plex on a Windows 10 server. I can connect securely locally from the server, other computers on my network, and remotely.

The issue I have is that I typically access my server through an SSH session with my router. When I go to plex.tv, I have to allow insecure connections to see the Plex server. Any suggestions on what may have changed recently that would cause this behavior?

Please explain that a bit more.
You should already get an encrypted connection if you (from outside your home network) go to plex.tv and simply click on ‘Launch’.

Do you use custom domains or VPN software?

Good point, this is more complicated than I remember. It’s been awhile since I set everything up.
When I am at work, I establish an SSH connection to my router. I like to use a tunnel so that I can keep what I do private.

Router:
runs squid proxy

Desktop
PuTTY with port 443 forwarded my squid port
My browser then uses that port to browse the internet

That’s probably not working then, because either the FQDN of your Plex server is not resolving (correctly) in your work browser or some DNS rebinding protection is interfering or some other DNS related issue.

See https://support.plex.tv/articles/206225077-how-to-use-secure-server-connections/
to get an overview how secure connections are working.

That being said: if you have already established a tunnel to your home router, you don’t need the additional layer of encryption. Since the tunnel you are using is already encrypted (at least I’m assuming that).

Thanks for that. I know you’re right I just don’t remember seeing that before.

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