Turning 65 — The Checklist to Work Down in the Year Before
A print-first sheet for the year you turn 65, ordered by deadline rather than by subject. Two of the items close doors that never reopen: the Part B late-enrollment penalty lasts for life, and the Medigap window that protects you from health underwriting happens once. Those sit at the top.
Works offline — your inputs never leave this device. How that works
Work down this sheet in the year you turn 65, in order. It is ordered by deadline rather than by subject, because the items near the top close doors that do not reopen: the Part B late-enrollment penalty lasts for life, and the Medigap window that protects you from health underwriting happens once.
Print it, keep it with your Social Security statement, and tick items with a pen. Nothing you do on this page is saved or sent anywhere.
Three months before you turn 65
This is when the doors open. Everything in this block is about being ready before the window rather than during it.
1. Work out your own seven-month window from your date of birth.
It opens three months before the month you turn 65.
The window is personal, and being born on the 1st of a month shifts the whole thing a month earlier because Social Security treats you as reaching 65 the day before your birthday. Generic advice misses that and it costs a month of coverage.
2. Establish whether you have coverage from CURRENT employment.
This one answer decides everything else on this sheet. Group coverage through your own or a spouse's current job lets you delay Part B with no penalty. COBRA and retiree coverage do not — both feel like continuous coverage and neither counts, which is the commonest route to a permanent penalty.
3. Ask your drug plan, in writing, whether its coverage is creditable.
Any plan offering drug coverage to Medicare-eligible people must tell you each year whether it is creditable, and that notice is what settles a penalty question years later. It arrives in the autumn looking like ordinary insurance mail. Keep it.
4. Find your Social Security statement and write down the benefit at full retirement age.
Every claiming figure on this site starts from that number rather than reconstructing it from your earnings record, so its answers can never disagree with your own paperwork. You will need it more than once.
The month you turn 65
The month the two one-off windows begin. Neither of them ever comes back.
5. Sign up for Part A and Part B, unless you are staying on current-employment coverage.
Sign up BEFORE your birthday month for coverage starting the 1st of it.
Sign up during or after your birthday month and coverage starts the month after you enroll, so the later you leave it the longer you are uncovered. If you are delaying because of current employment, that is a decision to record and revisit, not to forget.
6. Note the date your Medigap open enrollment window opens and closes.
Six months from the first month you are 65 or older AND enrolled in Part B.
During those six months an insurer cannot refuse you or charge more because of your health history. It happens once and does not repeat annually. After it closes, what you can buy may be narrower or more expensive, and for some people unavailable.
7. Check whether your income two years ago crossed an IRMAA threshold.
The surcharge is set from the return you filed two years earlier, so it can land in your very first Medicare year on income earned while you were still working full time. If a life-changing event has since reduced your income, Form SSA-44 is free to file.
Before the window closes
Three months after your birthday month, the Initial Enrollment Period ends.
8. Confirm your enrollment actually went through.
An application in progress is not coverage. Confirm in writing, and keep the confirmation: if a dispute about your enrollment date arises later, the burden of showing when you applied falls on you.
9. If you are delaying Part B, diarise the eight-month special enrollment period.
It runs from when the EMPLOYMENT ends, not when the coverage ends.
This is the trap that catches people who take COBRA at retirement: COBRA typically lasts eighteen months and the special enrollment period is eight, so enrolling when COBRA runs out is ten months too late.
10. Decide nothing about a plan on this sheet. Take that question somewhere free and unbiased.
Which coverage suits you turns on your doctors, your prescriptions, your travel and your health — none of which a checklist knows. Your state SHIP counselors are paid no commission and will sit down with you at no cost.
Your figures
These are the numbers this sheet asks for. Write them in once and the rest goes faster. They stay on the paper — nothing here is sent anywhere or saved.
The windows themselves, in Medicare’s own words
- Initial Enrollment Period (Part A and Part B)
- When: Seven months around your 65th birthday: it starts 3 months before the month you turn 65 and ends 3 months after that month. If your birthday falls on the 1st, the whole window shifts one month earlier — it starts 4 months before you turn 65 and ends 2 months after.
- What it lets you do: Sign up for Part A and Part B for the first time. Sign up in one of the 3 months before your birthday month and coverage starts the first day of the month you turn 65; sign up during your birthday month or in the 3 months after, and coverage starts the following month.
- General Enrollment Period (Part A and Part B)
- When: January 1 through March 31 every year.
- What it lets you do: Sign up for Part B (and premium Part A) if you missed your Initial Enrollment Period and do not qualify for a Special Enrollment Period. Since 2023 your coverage starts the month after you sign up — it no longer waits until July 1, which used to leave people uninsured for months. A late enrollment penalty usually still applies.
- Special Enrollment Period after employer coverage ends
- When: Starts the first month after your Initial Enrollment Period ends, and ends 8 months after the group health plan coverage or the employment ends, whichever happens first.
- What it lets you do: Sign up for Part B (and premium Part A) with no late enrollment penalty, based on your own or your spouse's current employment. Two traps: COBRA is not group health plan coverage and does not extend this window, and retiree coverage does not qualify either. If you sign up while still working, or within the first full month after employer coverage ends, you can ask to delay your Part B start date up to 3 months.
- Medicare Open Enrollment Period (Advantage and drug plans)
- When: October 15 through December 7 every year.
- What it lets you do: Join, drop or switch a Medicare Advantage plan (with or without drug coverage), switch between Original Medicare and Medicare Advantage, or join, drop or switch a Medicare drug plan. Coverage starts January 1 of the next year, and the plan must get your request by December 7.
- Medicare Advantage Open Enrollment Period
- When: January 1 through March 31, and only if you are already enrolled in a Medicare Advantage plan.
- What it lets you do: Switch to a different Medicare Advantage plan (with or without drug coverage), or drop your Advantage plan and go back to Original Medicare — in which case you can also join a separate Medicare drug plan. Coverage starts the first of the month after the plan gets your request. This window does not let you join an Advantage plan from Original Medicare.
- Medigap Open Enrollment Period
- When: Six months, starting the first month you have Medicare Part B and are 65 or older. It is one-time only — it does not repeat each year.
- What it lets you do: Buy any Medigap policy sold in your state at the best available price, with no medical underwriting: the insurance company cannot refuse you or charge you more because of pre-existing health problems. After this window closes you may not be able to buy a Medigap policy at all, or it may cost more. Missing it does not create a Medicare late enrollment penalty, but it can permanently change what supplemental coverage you can buy.
Two mistakes on this sheet cannot be undone later
A Part B late-enrollment penalty is charged for as long as you have Part B, which for most people means for the rest of their life, and there is no appeal for having simply been late. Medigap open enrollment happens once. Everything else here can be corrected; those two cannot, which is why they sit at the top.Where to take a plan question
We take no money from any insurer and name none, so we are not the place to settle what you buy. These three are, and all of them are free.
Verified 2026-08-02 against Medicare.gov, "When does Medicare coverage start?" (Initial, General and Special Enrollment Periods); plan windows from Medicare.gov, "Joining a plan" (https://www.medicare.gov/basics/get-started-with-medicare/get-more-coverage/joining-a-plan); Medigap window from Medicare.gov, "Medigap basics" (https://www.medicare.gov/health-drug-plans/medigap/basics) (effective 2026-01-01)
Estimate only — not financial, tax, legal, or insurance advice. Only MEDICARE can determine your actual amounts.
Official source: Medicare.gov — When does Medicare coverage start? ↗
🎓 Understand this tool
What it is
A sheet to work down in the year you turn 65, covering the enrollment decisions that have deadlines attached. It gathers what you need to have in hand, dates your own windows from your date of birth, and names the two mistakes at 65 that cannot be corrected afterwards.
How it works
The sheet is ordered by deadline rather than by subject, which is the opposite of how most Medicare checklists are arranged. That is deliberate: two of the items close doors permanently, and a sheet grouped by topic buries them among things that can be done any time. The windows themselves are rendered from the verified enrollment-windows pack, transcribed from Medicare's own pages, so the timing statements are theirs rather than our paraphrase.
Getting the most from it
- Print it. This is a sheet for a kitchen table and a pen, not a page to scroll — nothing you tick here is saved, on purpose.
- Start with the three months before your birthday month. Working out your own dates first makes every later item concrete rather than general.
- Answer the current-employment question early, because it decides most of the rest. Coverage from a job you or a spouse hold NOW is different from COBRA or retiree coverage, and only the first lets you delay Part B without a penalty.
- Keep the creditable-coverage notice your drug plan sends each autumn. It is the document that settles a penalty question years later, and it looks like junk mail.
- Take any plan question to Medicare's Plan Finder or a SHIP counselor. The sheet is finished when the dates and documents are in order — the choosing happens elsewhere.
Reading your result
Items with a date line are the ones with a deadline; the rest can be done in any order. The two permanent items — the Part B enrollment window and the six-month Medigap window — are at the top because their consequences last for life rather than for a year.
What it can't tell you
It cannot tell you whether your employer coverage qualifies, which is a determination Social Security makes, and it cannot tell you which coverage to choose, which depends on your doctors, your prescriptions and your health. It also does not cover the claiming decision for Social Security itself — a separate question with a separate wing.
Frequently asked questions
Three things, in this order: work out your own seven-month enrollment window from your date of birth, establish whether you have health coverage from CURRENT employment, and ask your drug plan in writing whether its coverage is creditable. Everything else on the sheet follows from those three answers.
Related calculators
Enrollment Dates
Your seven-month Medicare sign-up window is worked out from your birthday, and being born on the first of a month shifts the whole thing a month earlier. Enter your date of birth to estimate your own dates, see when coverage would start, and download them to your calendar. No email address required.
Late Penalty Calculator
Sign up for Medicare Part B or Part D late and the surcharge is permanent. Enter how many months you went without each kind of coverage to estimate what the penalty adds every month, every year, and over a horizon you choose. Part B counts full twelve-month periods only, so partial years cost nothing.
IRMAA Calculator
IRMAA is the income-related surcharge added to your Medicare Part B and Part D premiums when the tax return you filed two years ago showed income above a threshold. Enter that income and your filing status to estimate your tier, the monthly and yearly surcharge, and exactly how many dollars sit between you and the next cliff.
Annual update alerts — new tax and benefit figures the week they drop
One email when the numbers change. Double opt-in, no spam, unsubscribe anytime.