Hey @MScutra whats the exact enrollment/re-enrollment criteria? Could you send a screenshot?
My best guess here is that your enrollment is set on a filter of a property “status” equaling “not answering” and you re-enroll based on the status being that value?
If that’s the case, your re-enrollment will only trigger based on an update to the property, so if the status just stays as “not answering” there’s no action or update so no re-enrollment.
If the property was set to a different value and then back to “not answering” it would re-enroll. You’ll need some sort of action taken for re-enrollment to trigger.