@WillAdams have you seen the other threads with pocket issues such as this one:
Any guidance on that? Is 10% over the tool diameter a magic number that if exceeded the behavior is different? Advising a pocket that ends up cutting as a slot anyway is just a time consumer.
To be fair, I am not running the latest build of CC. When I get back from Vacation I intend to upgrade both CC and CM to the latest levels.