“juju debug-hooks” skips running your actual hook in favor of letting you do the steps manually in a terminal. My guess is you have something wrong (a typo, an incorrect step that is erroring) in your start hook or one of your other hooks. By running ‘juju debug-hooks’ you are skipping the hook. I would think ‘juju status’ would report what hook failed and the error that happened. You can use that to figure out what the problem is in your hook.
You can also look at “juju debug-log” which should report what hooks are running and what messages they are reporting.