Are you still working, with coverage through that job?

This is the question that changes every other answer. Active employer coverage at a large enough employer can let you delay Part B without penalty. COBRA and retiree coverage generally do not count as active employer coverage for this purpose — a distinction that catches people every year, because it feels like it should.

Has your window already opened?

Your initial enrollment period spans seven months: the three months before your birthday month, that month, and the three after. When you file inside that window affects when coverage starts, so the earlier part of it is worth more than the later part.

Do you want the option to change your mind later?

There is a separate six-month window, starting when you are 65 and enrolled in Part B, during which a Medigap carrier must sell to you regardless of your health. Outside of it, Michigan carriers can ask health questions. This is the quietest deadline of the set and the most expensive to miss.

(248) 761-2667 Contact us

The calendar

When to Enroll

Your seven-month window, the eight-month one after work ends, and the fall date most people miss.

Request a review or call (248) 761-2667

Medicare runs on windows. Miss one and the consequence is not a delay — it is usually a penalty, and several of them are permanent.

The windows are not complicated. They are just badly explained, and they differ depending on whether you are still working. Here they are in order.

The windows around 65

Miss one and the price tends to follow you.

3 mo beforeInitial enrollment opens — filing early is what gets coverage starting on time
65Medicare can begin. The Medigap window with no health questions opens with Part B
3 mo afterInitial enrollment closes
Employer +8The special window after active employer coverage ends — then penalties
Oct 15–Dec 7Annual enrollment — the yearly chance to change plans for January
Jan 1–Mar 31Medicare Advantage open enrollment — one change, if you are already in an Advantage plan

Still working at 65 with active employer coverage? Different rules entirely — which is exactly why the calendar comes before the shopping.

Windows reflect current rules for common situations; individual circumstances vary. Confirm your own dates before acting.

Three questions that set your dates

Are you still working, with coverage through that job?

This is the question that changes every other answer. Active employer coverage at a large enough employer can let you delay Part B without penalty. COBRA and retiree coverage generally do not count as active employer coverage for this purpose — a distinction that catches people every year, because it feels like it should.
Has your window already opened?

Your initial enrollment period spans seven months: the three months before your birthday month, that month, and the three after. When you file inside that window affects when coverage starts, so the earlier part of it is worth more than the later part.
Do you want the option to change your mind later?

There is a separate six-month window, starting when you are 65 and enrolled in Part B, during which a Medigap carrier must sell to you regardless of your health. Outside of it, Michigan carriers can ask health questions. This is the quietest deadline of the set and the most expensive to miss.

Let us put your actual dates on a calendar.

Get my dates

Bring three things

Your birthday, and your retirement date if you have one
Details of any coverage you have through an employer, now or ending soon
Your Medicare card or Social Security correspondence, if any has arrived

You leave with

Your specific dates written on a calendar
A clear answer on whether you can delay Part B without penalty
The one date you must not miss, marked

The dates are the easy part.

Nothing on this page is hard to understand. What makes it worth a conversation is that the right answer depends on your employer, your spouse's coverage, and whether you might want to switch paths later.

Ask about yours

Hypothetical

Someone who left work at 66 assumed COBRA counted as employer coverage for Medicare purposes. It does not. The eight-month special window closed unnoticed, and Part B arrived with a penalty attached for good — the kind of mistake that costs nothing to avoid if the calendar is in view a year early.

Hypothetical scenario for illustration. Not an actual client. Individual circumstances and results differ.