You can apply for Medicare Part B (outpatient services) during the year if, by your choice or the employer’s choice, you lose the employer coverage. There are 2 forms that will need to be completed (one you complete and the other form the employer completes) indicating the date of loss of coverage. Both forms will need to be taken to your local Social Security office in order to activate your Part B benefit. You would then be eligible for a special election period onto a Medicare Supplement/Medigap plan. At that time you will also want to enroll onto a stand-alone drug plan to cover your prescription drug needs.