Your Turning-65 Medicare Timeline

Six months before your birthday month: get organized

1. Make a list of your doctors, prescriptions, and pharmacies — you'll need it to compare plans later.
2. Create your my Social Security account at ssa.gov if you don't have one.
3. If you will still have coverage from a current employer at 65: Ask your employer's benefits administrator whether your drug coverage is “creditable” and how your plan works with Medicare — get it in writing.
4. If you will not have employer coverage at 65: Sketch a monthly budget for premiums, deductibles, and prescriptions.
5. If you will still have coverage from a current employer at 65: Contributing to a Health Savings Account (HSA)? Stop contributions 6 months before you apply for Medicare — Part A coverage is backdated up to 6 months when you sign up after 65.
6. Learn the basics: Parts A & B (Original Medicare), Part C (Medicare Advantage), Part D (drug coverage), and Medigap.

Three months before your birthday month: your enrollment window opens

1. If you will still have coverage from a current employer at 65: If your employer has 20 or more employees, the work plan pays first and you can usually delay Part B without penalty while you are still working — confirm with the employer's benefits office.
2. If you will still have coverage from a current employer at 65: If your employer has fewer than 20 employees, Medicare usually pays first — sign up for Parts A and B on time, or the work plan may not pay your bills.
3. If you will not have employer coverage at 65: Apply for Medicare Parts A and B at ssa.gov, by phone, or at your local Social Security office.
4. Enroll during these first 3 months and your coverage starts the first of your birthday month (the month before, if you were born on the 1st) — no gap.
5. Start comparing your two paths: Original Medicare + Medigap + Part D, or a Medicare Advantage plan.

Your birthday month (the month before, if you were born on the 1st)

1. If you enrolled early, your Medicare coverage begins on the 1st of this month.
2. If you enroll this month instead, Part B coverage starts the first of the month after you enroll.
3. Watch the mail for your Medicare card — it usually arrives about 2 weeks after you sign up. If it hasn't come, you can print an official copy from your Medicare.gov account.

The three months after: the window is closing

1. You can still enroll, but coverage now starts the 1st of the month AFTER you sign up — every month you wait is a month without coverage.
2. Enroll in the final month of the window and coverage starts the first of the month after that.
3. If you want a Medigap plan, your 6-month Medigap Open Enrollment starts when your Part B takes effect — guaranteed acceptance regardless of health.

After the window closes: your Initial Enrollment Period is over

1. If you will still have coverage from a current employer at 65: If you kept active employer coverage, you'll have an 8-month Special Enrollment Period when it ends — COBRA and retiree coverage do NOT count.
2. If you will still have coverage from a current employer at 65: But to join a Medicare drug plan or Medicare Advantage plan you only have 2 full months after the month your work coverage ends — much shorter than the 8-month Part B window.
3. If you will not have employer coverage at 65: Without a Special Enrollment Period, you wait for the General Enrollment Period (January 1 – March 31) and may owe a permanent Part B late penalty: 10% more per 12-month period you delayed, for as long as you have Part B.