I actually did this instead of tailscale first; installing tailscale on a pfsense router was a challenge, iirc i had to find and install the freebsd tailscale pkg from the command line because the plugin doesn’t give the option to connect to a non-tailscale control plane.

After I did that and connected to my headscale server (on my vps) I could ping pfsense’s local ip over the tailnet, but couldn’t get any traffic out from pfsense. Turns out I had forgotten the pfsense tailscale plugin automatically sets up outbound rules for you.

That was a rabbit hole I didn’t feeling like falling down, so I turned off headscale and just used tailscale account and the normal pfsense tailscale plugin. But it’s there and it does work fine if I ever wanted to go figure out the outbound traffic rules.

Headscale is the tailscale backend server

I’ve had immich running in a VM as a snap distribution for almost a year now and the experience has been leaps and bounds easier than maintaining my own immich docker container. There have been so many breaking changes over the few years I’ve used it that it was just a headache. This snap version has been 100% hands off “it just works”.

https://snapcraft.io/immich-distribution