Initially, I wanted to lean into my masochistic nature and configure my own VPN protocols with pfsense, but I only have one router and I didn’t want to fuck it up.
So, I opted for the simpler, quicker VPN setup - Tailscale. It’s absurdly simple - all you have to do is make an account, add your machine (s), click a couple of buttons for magic DNS, and you’re golden.
19/10/2025
Why did I torture myself.
It was worth it, though, since my connection is much more secure now. It turns out I had been exposing my Navidrome, which I should have noticed much, much earlier.
Also, I was stuck wondering what I should do after generating the certification and key. The Tailscale documentation doesn’t really tell me anything other than the command to generate the TLS certification and key. 1
So, I wasted even more time, REFERRING TO ANOTHER SOURCE, 2 when I could have just referred to an old source.
Regardless, this deserves it’s own topic.