Problem Statement
I have a whole mess of services that I host internally. I have them remotely available via Tailscale, but only via hostname and ports, and without SSL. I previously tried solving this problem with Nginx (huge pain, completely manual config), Traefik (way way way too magical), and Caddy (honestly cannot recall what my problem was), but couldn’t get it working reliably, so I stuck with hostname and ports. But that still left me with no SSL and certain services have to run over SSL to work, like local text-based assistants in Home Assistant, and various rich notifications on iOS, so… it’s time to fix this.