I managed to reproduce on a caas model with 2 related applications
$ juju destroy-controller ian --destroy-all-models -y Destroying controller Waiting for hosted model resources to be reclaimed Waiting on 2 models, 3 machines, 7 applications Waiting on 2 models, 3 machines, 7 applications Waiting on 2 models, 3 machines, 6 applications Waiting on 2 models, 3 machines, 2 applications Waiting on 2 models, 3 machines, 2 applications Waiting on 2 models, 3 machines, 2 applications Waiting on 2 models, 3 machines, 2 applications ...
I managed to reproduce on a caas model with 2 related applications
$ juju destroy-controller ian --destroy- all-models -y
Destroying controller
Waiting for hosted model resources to be reclaimed
Waiting on 2 models, 3 machines, 7 applications
Waiting on 2 models, 3 machines, 7 applications
Waiting on 2 models, 3 machines, 6 applications
Waiting on 2 models, 3 machines, 2 applications
Waiting on 2 models, 3 machines, 2 applications
Waiting on 2 models, 3 machines, 2 applications
Waiting on 2 models, 3 machines, 2 applications
...