The biggest issue I have with Caddy and running ancillary services as some services attempt to utilize port 80 and/or 443 (and may not be configurable), which of course isn’t possible because Caddy monopolizes those ports. The best solution to this I’ve found is to migrate Caddy and my services to docker containers and adding them all to the same “caddy” network.

With your caddy instance still monopolizing port 80 and 443, you can use the Docker expose or port parameters to allow your containers to utilize port 80 and/or 443 from within the container, but proxify it on the host network. This is what my caddy config looks like;

{
        admin 127.0.0.1:2019
        email {email}
        acme_dns cloudflare {token}
}
domain.dev, domain.one {
        encode zstd gzip
        redir https://google.com/
}
*.domain.dev, *.domain.one {
        encode zstd gzip
        @book host bk.domain.dev bk.domain.one
        handle @book {
                reverse_proxy linkding:9090
        }
        @git host git.domain.dev git.domain.one
        handle @git {
                reverse_proxy rgit:8000
        }
        @jelly host jelly.domain.dev jelly.domain.one
        handle @jelly {
                reverse_proxy {ip}:8096
        }
        @status host status.domain.dev status.domain.one
        handle @status {
                reverse_proxy status:3000
        }
        @wg host wg.domain.dev wg.domain.one
        handle @wg {
                reverse_proxy wg:51820
        }
        @ping host ping.domain.dev ping.domain.one
        handle @ping {
                respond "pong!"
        }
}

It works very well.

We’ll need to see configs and IP assignments to be able to help.

I’m not sure if this will help you out since I’m really not sure what your problems are other than getting the reverse proxy to work. So, I’ll give you what I’ve found to work and if it’s not what you were looking for then you can just skip over what I"m yammering on about.

The process:

Spin up a container, let’s say it’s Dozzle and it needs port 1124. Container deployed, so lets put it in reverse proxy:

Issue command together:

sudo nano /etc/caddy/Caddyfile
sudo systemctl restart caddy	

Enter the following in the Caddyfile:

dozzle.myverycooldomain.duckdns.org:443 {
	reverse_proxy localhost:1124
}

Press ctrl x, press y, press enter, and the Caddy server restarts if you indeed issued the commands together. Now go to dozzle.myverycooldomain.duckdns.org for test run.

Have you tried the Caddyfile from Lemmy-Easy-Deploy?