Formalizing this into an issue from @G-Rath's comment here.
It might be worth reviewing the output later at some point:
❯ bundle exec rake dev:annotate
Chusaku has finished running.
Model files unchanged.
❯ bundle exec rake dev:annotate
Nothing to annotate.
Model files unchanged.
Specifically, removing that leading newline, and changing the "Nothing to annotate" to "Controller files unchanged" or something similar to make it clearer what it's referring to.
Formalizing this into an issue from @G-Rath's comment here.