Follow-up: I have Caddy working!

Here's my baseline before starting:

• Services running on my NAS already configured
• Domain names & DNS already hosted at Porkbun
• Dynamic DNS in place using https://hub.docker.com/r/qmcgaw/ddns-updater
• DNS includes wildcard support, so I can easily use anything.mydomain.net

After briefly trying out a couple of somewhat ingrated Caddy projects others have done, I decided they were too specific to their set-ups and did not make my life easier. I tossed them out and went simple. I wanted something super easy to understand, and thus easy to troubleshoot.

First I set it up in Docker. I created a really, really simple docker compose file:

version: "3.7"

services:
  caddy:
    image: caddy:alpine
    restart: unless-stopped
    ports:
      - "1080:80"       # Because Synology DSM reserves 80 for itself
      - "10443:443"     # Because Synology DSM reserves 443 for itself
      - "10443:443/udp" # Because Synology DSM reserves 443 for itself
    volumes:
      # next four lines are default
      # - $PWD/Caddyfile:/etc/caddy/Caddyfile
      # - $PWD/site:/srv
      # - caddy_data:/data
      # - caddy_config:/config
      - /var/docker/caddy/config/Caddyfile:/etc/caddy/Caddyfile
      - /var/web:/srv # serve this by default?
      - /var/docker/caddy/data:/data
      - /var/docker/caddy/config:/config

volumes:
  data:
    external: true
  config:
    external: true

(If the machine you are running Caddy on doesn't reserve ports 80 and 443 for itself like Synology DSM does, you don't need the ridiculous high ports I mapped. Just do 80:80 and 443:443.)

Then I created a simple Caddyfile.

web.fakeme.net, www.fakeme.net {
	# This connects to the default Synology web service
	reverse_proxy 192.168.2.15:80
}

This tells Caddy: When you get a request for web or www, send it to the machine at 192.168.2.15 using port 80.

Then I added to it, one service at a time to make sure things worked at each step

paperless.fakeme.net {
	reverse_proxy 192.168.2.15:8008
}

whoami.fakeme.net {
	reverse_proxy 192.168.2.15:8009
}

comics.fakeme.net {
	reverse_proxy 192.168.2.15:8010
}

plex.fakeme.net {
	reverse_proxy 192.168.2.15:32400
}

speedtest.fakeme.net {
	reverse_proxy 192.168.2.15:8011
}

You'll note I am doing nothing fancy here – no hostnames, no dynamic Docker container checks, none of that crap. It's brittle but it is dead simple.

Now that I have something simple working, I can get fancier if I feel like it.

reddit's r/homelab and r/selfhost were my go-tos, but Spez decided to kill the golden goose, so I left. I've been trying to help the Kbin and Lemmy communities grow, but we'll see how it goes…

Oh! Also Tildes! It's been established for a while but the user base isn't huge since it's still in beta. LMK if you'd like an invite.

I did find this there… indicating there is some activity around self-hosting:
https://tildes.net/~comp/16yc/self_hosters_share_your_reasons_for_self_hosting_and_favorite_apps

This may help: https://caddy.community/t/using-caddy-as-a-reverse-proxy-in-a-home-network/9427

I am just starting the same journey and have also experienced the lack of good guides for noobs. Most guides are on integrating more complex setups.