First off, I think I have the right basic plan but am open to exploring some others, especially if I have some basic assumptions wrong.

GOAL: Allow myself and family to access my various hosted apps without needing to teach VPN or Tailscale.

What I have: Proxmox with Home Assistant VM and some additional LXC containers. I do not intend to do Docker, not interested unless I have to (actually, isn’t HAOS using Docker, but beyond that one.) IT Tools is one nice to have I want to get to from work and works as a good test case. Some other LXCs are one for Caddy and one for PiHole. Also, I registered a personal domain through CloudFlare.

PLAN: Get Caddy working internally using PiHole pointing my domain to the internal IP of Caddy and CloudFlare Tunnels and DNS to help get to services from outside going Cloud flare -> Caddy -> service.

I don’t know why but nothing I tried seems to work, I can’t find a good Caddy HowTo or maybe the relatively recent update of Caddy to v2 changed things??? I don’t know. But I really just need some help walking through some of this Caddy setup.

I am going to make another attempt today and will replay with progress. But right now Caddy file is basically back to original OTB. I did add the module for CloudFlare and at one point confirmed that was loaded. I assume that module is needed to get Caddy to talk to CF DNS to confirm I own the domain for creating the certs, but I couldn’t figure out what to do with the token, one guide had me adding something to the Caddy file but that just created an error.

So any comments on the plan or insightful nuggets would be appreciated.