At a glance
Start with these three things.
Check your employer plan
Ask how it works with Medicare.
Watch HSA timing
Medicare enrollment affects contribution eligibility.
Plan your transition
Confirm dates before employer coverage ends.
Your questions, unpacked
Working past 65: your questions, answered.
Ask how your coverage coordinates
Confirm whether your insurance is based on your or your spouse’s current employment, the employer’s size, and which coverage pays first. Those details affect your next step.
Retiree coverage and COBRA are not the same as coverage from current employment for Medicare enrollment purposes.
Plan the transition before retirement
You may qualify for a Special Enrollment Period when current employment or the related coverage ends. Confirm the applicable deadline and arrange effective dates before you leave your job.
Prescription coverage has its own creditable-coverage rules. Keep any notices that explain whether your current drug coverage meets that standard.
Include your HSA in the discussion
If you contribute to a Health Savings Account, Medicare enrollment can affect your eligibility to contribute, including when Part A starts retroactively.
Discuss the timing with your benefits administrator and a qualified tax professional. A broker can help explain the Medicare coverage choices alongside that advice.
Health savings accounts need their own timeline
You cannot contribute to a Health Savings Account once you are enrolled in Medicare. Medicare advises stopping HSA contributions six months before retiring or applying for Social Security or Railroad Retirement benefits, because Part A coverage can be retroactive.
Ask your benefits administrator how employer size and coverage affect which insurance pays first. Do not assume COBRA or retiree coverage gives you the same enrollment protection as coverage based on current employment.
Sources & further reading
Related guidance