After I retire, can I enroll in a family plan or do I have to be enrolled in a Self and Family plan for the five years before I retire in order to continue it into?
No, you do not have to be enrolled in a family plan for the five years before you retire to meet the five-year requirement. As a retiree, you can enroll in a family plan during the Open Season or when an event occurs that permits a change to the family plan.
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