i added this mod to my dedicated server and it doesn't ever load up, it's never even mentioned in the start up log.

what would cause it to never even try to load the mod?

Are there other mods that do load correctly? Did you also include Cargo Ships Graphics? It won't load if the dependency is missing.

added graphics addon for cargo ships and boom now its loaded, guess that is a requirement lol

ya, ran into this too. can we add the requirment to the top-level page that servers must manually install dependencies?

That's not specific to this mod, though.... Headless never downloads anything from the mod portal. Always test your mod pack on a single player map before starting a server :)