When attempting to complete enrollment within 10 days prior to the due date or after the due date has passed for the current month, you receive an error stating such and are not able to proceed with enrollment until that is corrected. Getting around this involves refreshing the payment plan to drop the offending month, completing enrollment, then going back and refreshing the payment plan while overriding late enrollment settings.

A button to override this when completing enrollment from Pending Families instead of going through the above process would be incredibly handy.