Retiring, or working past 65

Still working at 65

If you have coverage through active employment, you may be able to delay Part B without a penalty. Whether you can depends largely on employer size — the rules differ for smaller employers, where Medicare often becomes the primary payer — and on whether your coverage counts as creditable.

Part A is a separate question. It is usually premium free, but enrolling in it stops you from contributing to a health savings account. If you are funding an HSA, that timing matters and is worth planning around before your birthday, not after.

When you retire or lose the group plan

Leaving employer coverage generally opens a Special Enrollment Period for Part B, typically running eight months from when the employment or the coverage ends, whichever comes first. Drug coverage runs on a shorter clock, so the two do not line up and people miss the second one while attending to the first.

COBRA is where this most often goes wrong. COBRA is not considered coverage from active employment, so continuing on COBRA past 65 usually does not protect you from a Part B late enrollment penalty. People assume it does, keep COBRA for a year, and inherit a penalty that lasts as long as they have Part B.

What we do about it

We look at your actual dates — birthday, retirement date, when coverage ends — and work backward to tell you what to file and when. If a supplement is the right route, we make sure the application lands inside your open enrollment window, when health questions cannot be asked. If a Medicare Advantage plan fits better, we check your doctors first.