I’ve been using Tailscale as the VPN for my homelab for a while now, but I’d never actually tried to access my internal services from a remote location until recently. Turns out, just being on the tailnet doesn’t mean everything magically works - there were a few layers of configuration (and one very long detour) between “connected to Tailscale” and “watching Jellyfin from a hotel room.”¹

I know just enough about computer security to know that I don’t know enough about computer security, so I default to keeping my systems as closed-off from the outside world as possible. I use Cloudflare Tunnels for the few systems that I want to make externally available¹ (like Gitea), and Tailscale to access “internal” services or ssh while on-the-go.