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.