Caddyfile with multiple sites

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1

I’m working on setting up some self-hosted service and running into some issues with the proxy server. I’m a hobbyist w/ under 2yrs experience with web/hosting services so pardon me if I’m missing an obvious answer.

Using a RPi4 as host and running everything through docker. I’ve got a Caddy container and Airsonic container playing nicely. So airsonic.mydomain.com works just fine. The nextcloud and postgres container play just fine and run alone can be used and accessed locally. However, when I try to add the proxy for the nextcloud container the entire thing falls apart. By that I mean the airsonic, nextcloud and, postgres containers start up just fine, the caddy container seems to stick on restarting. Only difference is the new caddyfile and starting all four services from a single docker-compose.yml.

My working caddyfile with the additions for multiple proxies commented out

pi@rpi4:/media/storage/data/airsonic $ cat ../caddy/Caddyfile 
#mydomain.com {
#    root  /www/mydomain.com
#}
#
music.mydomain.com {
    proxy / http://loc.al.ip.03:4040 {
        transparent
    }
}
#
#cloud.mydomain.com {
#    proxy / http://loc.al.ip.002:80 {
#        transparent
#        web-socket
#    }
#}

If it helps here is the docker-compose.yml in which the caddy container get stuck restarting

---
version: "2"
networks:
  static-network:
    ipam:
      config:
        - subnet: 172.20.0.0/16
          ip_range: 172.28.5.0/24
services:
  db:
    image: postgres:alpine
    container_name: cloud-db
    restart: always
    volumes:
      - /media/storage/data/nextcloud/database:/var/lib/postgresql/data
    env_file:
      - /media/storage/data/nextcloud/db.env
    networks:
      static-network:
        ipv4_address: 172.20.0.1
  cloud:
    image: nextcloud:apache
    container_name: cloud-service
    links:
      - db
    environment:
      - POSTGRES_HOST=db
      - PUID=33
      - PGID=33
    env_file:
      - /media/storage/data/nextcloud/db.env
    volumes:
      - /media/storage/data/nextcloud/html:/var/www/html
      - /media/backup/nextcloud:/var/www/html/data
    depends_on:
      - db
    restart: always
    networks:
      static-network:
        ipv4_address: 172.20.0.2
  airsonic:
    image: linuxserver/airsonic
    container_name: audio-stream
    environment:
      - PUID=1000
      - PGID=1000
      - TZ=America/Chicago
    volumes:
      - /media/storage/data/airsonic/config:/config
      - /media/music:/music
      - /media/storage/data/airsonic/playlists:/playlists
      - /media/storage/data/airsonic/podcasts:/podcasts
    networks:
      static-network:
        ipv4_address: 172.20.0.3
    restart: unless-stopped
  caddy:
    image: jessestuart/caddy
    container_name: proxy-service
    environment:
      - ACME_AGREE=true
    volumes:
      - /media/storage/data/caddy/.caddy:/root/.caddy
      - /media/storage/data/caddy/Caddyfile:/etc/Caddyfile
    networks:
      static-network:
        ipv4_address: 172.20.0.99
    ports: 
      - 80:80
      - 443:443
    restart: unless-stopped

Any help would be great, I’m stuck at the moment.