Tailscale and Plex: Setup Wizard not Running

This is mostly a reminder for my future self in case I’m going to set up Plex via Tailscale again.

I set up a VM and installed Tailscale on it to have it part of my mesh VPN to access it from all my devices without exposing it directly to the internet. Alongside Tailscale, I installed Plex as well to access my media files.

To access the Plex Web Application, I opened the Tailscale provided hostname/IP Address with Plex’ Port :32400 in my browser, like so: http://100.67.23.42:32400. The Plex Web Page did load but didn't start the Setup Wizard to add my Media Libraries, which was quite confusing to me.

Turns out, in order to set up Plex locally, it requires to run or be accessed through an rfc1918 IP Address. The one you have probably configured for your router or other systems locally:

10.0.0.0 - 10.255.255.255  (10/8 prefix)
172.16.0.0 - 172.31.255.255  (172.16/12 prefix)
192.168.0.0 - 192.168.255.255 (192.168/16 prefix)

Tailscale uses reserved address space from rfc6598 (100.64.0.0/10) they have this also documented here.

So, in order to just set up the Plex Server, I created an SSH tunnel through the main host which was on my private lan to configure Plex. Fortunately, after it’s configured it can be accessed through the Tailscale IP/Hostname.