It is the number of days to look back if users have either self-enrolled or their manager have enrolled them into a course and completed it, then the assignment will not enroll them again. If the user has not completed the assignment (still in "enrolled" status), the user will get converted over to the new assignment and have the new due date.
The Lookback Days setting does NOT take into consideration, if the user was already enrolled from another assignment. It will enroll the user again because assignments are setup with mandatory courses.
Note:
Most clients are setup with a default 'Look Back Days' period (e.g. 15 days or 30 days). If the field is left blank will still look back those number of days.