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Because the system does not have a good way of handling this kind of workflow where a student might have been enrolled, withdrawn and then re-enrolled again, having both values filled will likely cause complications on the record.
It is advised to simply remove any values present for a Date Withdrawn and a Late Date Enrolled should the student be expected to be enrolled in the class. If you need to track that a student was withdrawn and re-enrolled, you should store that data in the Notes field on the Other tab of the Class Enrollment record.