Hi @Jtischler if your  enrolment rules were create after the group it will not work retroactively...I usually create the group but don't activate it; then create the enrolment rule with the new group, then go back to the group to activate it...try that to see if it works.

@lrnlab  - I purposely did not use enrollment rules so that 100% of the group being direct enrolled to the Learning Plan would receive the assignment, and then subsequent new members to group would also receive the assignment.  Is it expected functionality for groups that are direct enrolled to a LP to not assign the LP to new members of group as they get added?