Checklist
Turning 65: a Medicare checklist, month by month
Your 65th birthday starts a 7-month window to sign up for Medicare, and a few decisions in it are hard to undo. Here's what to do, roughly when, and the questions to settle before you sit down with an agent.
Last reviewed October 26, 2026. General information, not advice about any plan.
The timeline
4 to 6 months before your birthday month
Decide whether you'll keep working and keep job-based coverage. Gather your doctors and prescriptions. Find an agent or your state's free SHIP counselor.3 months before
Your Initial Enrollment Period opens. Sign up through Social Security now if you want Part A and Part B to start the month you turn 65. Compare plans and enroll in the one you choose.Your birthday month
Coverage starts if you signed up early. If you're signing up now, Part B starts next month.Up to 3 months after
Your window closes at the end of the third month after your birthday month. After that, you may wait until the General Enrollment Period and pay a penalty.
If you're still working
- Employer with 20+ employees
- Your job's plan usually pays first, and you can often delay Part B without a penalty while you're covered by current employment (yours or your spouse's).
- Smaller employer
- Medicare usually pays first, so you'll generally want Part A and Part B when you're first eligible.
- When the job or coverage ends
- You have 8 months to sign up for Part B without a penalty, counted from when the job or the coverage ends, whichever is first. COBRA and retiree coverage don't extend it.
- Health savings account
- Once you have Medicare you can't add money to an HSA, and Part A can start up to 6 months back when you sign up after 65. Talk to the employer before you enroll.
Choosing how to get coverage
Most people end up with one of two set-ups:
- Original Medicare + Medigap + Part D
- Any doctor who takes Medicare, nationwide. You pay a Medigap premium, and a drug plan premium. Your best time to buy Medigap is the 6 months after your Part B starts, when insurers can't turn you down.
- Medicare Advantage
- A private plan that covers Part A and B services, usually with a network and often drug coverage and extra benefits. Costs and networks vary a lot by plan.
Which fits depends on your doctors, prescriptions, budget and travel. A licensed agent can compare plans for your situation; here's what to bring.
Mistakes that cost the most
- Missing your window for Part B without job-based coverage: 10% more on your premium for each full year you went without, usually for life.
- Going without drug coverage: a Part D penalty for each month without Part D or other creditable coverage, for as long as you have drug coverage.
- Waiting until COBRA ends to sign up for Part B. The 8-month window starts when the job or job coverage ends.
- Letting your Medigap open enrollment pass, then finding insurers can ask health questions later.
Common questions
Will I be signed up for Medicare automatically?
If you already get Social Security or Railroad Retirement benefits when you turn 65, you're usually enrolled in Part A and Part B automatically and your card arrives in the mail. Otherwise, you sign up through Social Security.
When does my coverage start?
If you sign up in the 3 months before your birthday month, Part B starts the month you turn 65. If you sign up in your birthday month or later in the window, it starts the month after you sign up.
Do I have to take Part B if I'm still working?
Not always. If you're covered through your own or your spouse's current job at an employer with 20 or more employees, you can usually delay Part B without a penalty. Check with the employer's benefits office first.
When should I talk to an agent?
About 3 to 4 months before your birthday month is a good time: early enough to compare plans and enroll so coverage starts on time.
Keep reading
- Medicare enrollment periods: when you can sign up or switchEvery Medicare enrollment window in one place: turning 65, the fall Annual Enrollment Period, the January–March change, Medigap open enrollment, special periods and late penalties.
- Medicare late enrollment penalties: how they work and how to avoid themHow the Part B, Part D and Part A penalties are figured, with 2026 examples, the situations that let you sign up late without one, and how to challenge a penalty you think is wrong.
- Medicare's free preventive care and yearly wellness visit, explainedWhat the "Welcome to Medicare" and yearly Wellness visits include (and why they aren't a physical), the screenings and vaccines Medicare covers at no cost, and when a "free" visit can still lead to a bill.
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