On the startup command please ignore the space between . com. This site wouldnt let me post without adding that space because too many links for new user
So Ombi is an application tied into plex that runs its own webserver. If i go to mydomain.com:5000 I can reach it from outside my network. However my goal is to get it so I just have to go to mydomain.com and reach it.
You just need to ensure that Caddy is reading from the Caddyfile you want it to.
Ditch the -host flag and use -conf instead; Caddy should figure out the hostname from your Caddyfile.
C:\Caddy\caddy.exe -conf C:\path\to\Caddyfile
P.S.: mydomain.com is owned by a registrar and is currently hosted by an Apache server. example.com is the right domain to use for demonstration or example purposes.