TL;DR Link to heading On macOS Mojave Gatekeeper only verifies executables, which are run with the open command or the user double clicks. It won’t verify files, that are executed through other means like, directly executing a binary ./myapp regardless of the quarantine attribute. If you can place a plist file inside LaunchAgents/LaunchDaemons, the command inside will also be executed. Prior to Catalina there is a way to trick users to drag & drop files in the LaunchAgents folder.