Turning 65? Here's what to do, and when
Medicare has deadlines with permanent penalties attached, and the right sequence depends on whether you're still working. This is the checklist I walk new clients through — start about six months before your birthday.
Your Initial Enrollment Period runs three months before to three months after your 65th birthday month. Enrol in Parts A and B unless you have creditable employer coverage from a large employer, decide between Medicare Advantage and Original Medicare with Medigap, and add Part D. Start about six months out; in the Capital Region I do this at no fee.
Six months out: know your situation
- Are you (or your spouse) still working with employer health coverage? This single question decides most of the timeline. Check how many employees the employer has — 20 is the line.
- Are you already receiving Social Security? If so, Medicare Parts A and B will start automatically the first of your birthday month; a card arrives about three months before.
- Do you have an HSA? Plan your last contribution — see the FAQ below.
- Do you have VA, TRICARE, union or retiree coverage? Each interacts with Medicare differently; bring the details to our call.
- List your doctors and prescriptions. Everything else in Medicare gets compared against this list.
Three months out: enroll in Parts A and B
If you're not receiving Social Security, you apply for Medicare yourself at ssa.gov/medicare — it takes about ten minutes online. Apply in the three months before your birthday month so coverage starts on the 1st of that month with no gap.
- Part A is premium-free for almost everyone who worked 10 years. Take it at 65 unless you need to keep contributing to an HSA.
- Part B has a monthly premium. Take it at 65 unless you're covered by a plan from your or your spouse's current employment. Employer size decides who pays first: with 20 or more employees the employer plan is primary and delaying is usually sensible; with fewer than 20, Medicare is primary and delaying leaves bills unpaid even though a Special Enrollment Period may still exist. Delaying with no qualifying coverage at all means a permanent penalty of 10% of the premium for every 12 months you were late — and a wait until the next General Enrollment Period to get in.
Two months out: choose how to fill the gaps
Original Medicare alone leaves you exposed — no drug coverage and no cap on out-of-pocket costs. You'll choose one of two paths:
Path 1: Original Medicare + Medigap + Part D
Any doctor who accepts Medicare, no networks or referrals, predictable monthly premiums. In New York you can join a Medigap plan any month with no health questions.
Medigap in NY →Path 2: Medicare Advantage
One private plan with a network, usually including drug coverage and extras, often $0 premium beyond Part B, with copays when you use care and a yearly out-of-pocket cap.
Medicare Advantage →Whichever path you take, you need Part D or other creditable drug coverage from the start. After your Initial Enrollment Period, going 63 consecutive days or more without it triggers a permanent late-enrollment penalty — even if you take no medications today.
Do this before you pick a plan
New York's Medicare Savings Programs, Extra Help and EPIC have higher income limits than most people assume and no asset test for MSP. Qualifying changes which plans make sense, so check first.
If you're still working past 65
- Confirm with HR that the employer plan is creditable for drug coverage and that the employer has 20+ employees. Get it in writing.
- Take Part A (unless you have an HSA) and delay Part B and Part D.
- When you stop working or lose the coverage, you have an 8-month Special Enrollment Period for Part B and a 2-month window for Part D or Medicare Advantage — the drug window is the one people miss.
- Ask HR for form CMS-L564 (proof of employer coverage) when you leave; Social Security will want it.
Where Social Security fits
Turning 65 does not mean claiming Social Security. Your full retirement age is 67 if you were born in 1960 or later, and your benefit keeps growing until 70. Many people take Medicare at 65 and claim Social Security years later — the Part B premium is simply billed to you quarterly until then. As a Registered Social Security Analyst, I can run your claiming scenarios in the same conversation.
Common mistakes I see
- Assuming COBRA or retiree coverage lets you delay Part B. It doesn't.
- Skipping Part D "because I don't take anything" and paying the penalty for life.
- Choosing a plan from a TV ad without checking whether your doctors are in the network.
- Not stopping HSA contributions in time.
- Not checking for cost help before choosing a plan.
- Never reviewing the plan again after the first year, while networks and drug lists change every January.
A single call three to six months before your birthday helps you avoid all of these. Book a turning-65 review — there's no fee for Medicare plan help.
- When does Medicare coverage start? (medicare.gov) — 7-month window, 8-month SEP, COBRA rule
- Working past 65 (medicare.gov) — 20-employee rule, HSA 6-month rule
- Avoid late enrollment penalties (medicare.gov)
- Part D late enrollment penalty (medicare.gov)
I do not offer every plan available in your area. Any information I provide is limited to the plans I do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your State Health Insurance Assistance Program for information on all of your options. Not connected with or endorsed by the U.S. government, the Social Security Administration or the federal Medicare program.
Common questions
Short answers to what people ask before they call.
When exactly is my Initial Enrollment Period?
Seven months: the three months before the month you turn 65, your birthday month, and the three months after. If your birthday is on the 1st of a month, the window shifts one month earlier. Enrolling in the three months before your birthday month gets you coverage starting the first of your birthday month.
I'm still working and have insurance through my job. Do I have to take Medicare at 65?
If your employer has 20 or more employees, you can delay Part B (and Part D) without penalty while you're covered by that plan, and you get an 8-month Special Enrollment Period when the job or the coverage ends. Most people still take premium-free Part A. If the employer has fewer than 20 employees, Medicare generally becomes primary and you should enroll on time.
Does COBRA count as employer coverage for delaying Part B?
No. COBRA and retiree coverage do not let you delay Part B without penalty. This catches people every year — if you leave work at 64 and take COBRA, you still need to enroll in Part B in your Initial Enrollment Period.
I contribute to a Health Savings Account. Anything I should know?
Yes: you can't contribute to an HSA once you're enrolled in any part of Medicare. And if you claim Social Security after 65, Part A is backdated up to six months — so stop HSA contributions six months before you plan to enroll, or you'll owe tax on the excess.
Do I need to claim Social Security to get Medicare?
No. They're separate. If you're already receiving Social Security at 65 you'll be enrolled in Parts A and B automatically; if not, you apply for Medicare on its own through ssa.gov and can keep delaying Social Security. When to claim Social Security is its own decision.
Let's talk it through
A phone call or a message is all it takes. The first conversation is just a conversation.