Learning Plan Message Behavior

Summary

Need confirmation for behavior of Learning Plan messages when changed between user mapping

Content

Learn Logic is antithetical to my logic at times.... so, although I think I know the answer, I need you all to reassure me that my thinking is Learn compatible. 

I'm manually mapping users to a recurring Learning Plan using the Bulk Loader.  The users fall into categories:

1. Users out of compliance (last completion in 2016 or pre-May 2017) -- these users will be mapped to the plan using their last completion date as the assignment date.  They need to complete the training now.  I would like to have an email that "notifies" them that they were identified in our training compliance audit as not having received the assignment since 2016 (essentially a lie, but no matter.)