Question: I am about to retire and have secured independent coverage beginning 2 months before my actual retirement date. Can my company insurance carrier require me to stay on my plan until my retirement date or can I drop their coverage now?
Answer: In order to drop your group health insurance before the end of the plan year (open enrollment period), there has to be a qualifying event. For example, your retirement is a qualifying event. So you cannot drop your group health insurance coverage before your retirement date. Your mistake was in setting the effective date of your individual health insurance plan two months early. You can probably change that, ask your individual plan carrier to put off your effective date. If you show that you have coverage until then, there should be no problem.