Turning 65
The Medicare roadmap for the year before you turn 65
Five moments that actually have deadlines attached, in the order they happen. No plan names, no recommendations — just what's due when, and what it costs if you miss it.
Free, and you don't have to give us anything to read or download it.
Why the timing matters more than the plan
If you don't sign up for Part B when you're first eligible and you don't qualify for a Special Enrollment Period, you'll pay an extra 10% of the Part B premium for each 12-month period you could have had it and didn't — and in most cases you keep paying that penalty for as long as you have Part B. It is one of the few mistakes in Medicare that never stops costing.
Medicare.gov — Avoid late enrollment penalties- 12
months before
Answer one question: will you still be working at 65?
Everything else on this timeline branches off that answer. If you'll have coverage through your own or a spouse's active employer, you may be able to delay Part B without a penalty. If you won't, your enrollment window is fixed and the penalty for missing it is permanent. This is also the moment to decide when you want Social Security to start, because that decision can enroll you in Medicare automatically.
- Find out whether your employer plan counts as creditable coverage — the rules differ depending on the size of the employer.
- Decide, at least provisionally, when you want Social Security to begin.
- If you're already receiving Social Security or Railroad Retirement benefits, you'll be signed up for Part A and Part B automatically — so check whether that applies to you.
- 6
months before
If you have an HSA, plan your last contribution now
This is the step almost every roadmap leaves out, and it costs people real money. When you enroll in Part A after turning 65, coverage can be backdated by up to six months — and you cannot contribute to a health savings account for any month you're considered covered. Contributions made in those backdated months become excess contributions, with tax consequences.
- Work out your final HSA contribution month, counting back about six months from when your Part A will start.
- Tell your employer or HSA administrator so payroll contributions stop on time.
- You can still spend what's already in the account after you enroll — the restriction is on putting money in.
- 3
months before
Your enrollment window opens
Your Initial Enrollment Period is seven months long: the three months before the month you turn 65, your birthday month itself, and the three months after. Signing up in the first three months is the version where your coverage is in place the day you're eligible, with no gap.
- Enroll in Part A and Part B through Social Security — unless you're delaying Part B because of employer coverage, or you're being enrolled automatically.
- If you sign up during these three months, coverage starts the first day of your birthday month. (If your birthday falls on the 1st, it starts the first day of the previous month.)
- Waiting until after your birthday month is allowed, but it pushes your start date later.
- 0
your birthday month
Coverage begins, and your card arrives
Your red, white and blue Medicare card comes in the mail. Coverage always starts on the first of a month. Now is the point at which the coverage decisions become real ones rather than hypothetical, and it's worth understanding the two broad directions before anyone asks you to choose.
- Check that your card shows the parts you expected to be enrolled in.
- Confirm your doctors and your prescriptions against whatever coverage you're considering — this is the step people skip and regret.
- Take your time. Nobody needs an answer from you today.
- +6
months after Part B
The window most people don't know exists
For six months, beginning the first month you have Part B and are 65 or older, you have a one-time Medigap Open Enrollment Period. During it, a Medicare Supplement insurer cannot turn you down or charge you more because of your health history. Once it closes, your medical history can affect whether you can buy a policy at all — and that is permanent. No other deadline on this page has consequences that last as long.
- Know your six-month window and the date it closes.
- If a Medicare Supplement policy is something you might ever want, this is the cheapest and safest time to get one.
- California extra: after that, state law gives you a 60-day window following your birthday each year to switch to a Medigap policy with equal or lesser benefits, without new medical underwriting.
The hard part isn't understanding this. It's remembering it a year from now.
Most people read a page like this once, agree it makes sense, and then meet the deadline by accident or miss it entirely. So we'll send it to you in pieces, timed to your birthday, roughly a month before each step is due.
That's all it is. We don't sell your information, we don't call you, and there is no obligation to ever become a client. If you'd rather just read it and get on with your day, that's genuinely fine — the PDF is free and ungated.
When you want to talk it through with a person
A timeline can tell you what's due. It can't tell you how your employer coverage interacts with Part B, or what happens to your spouse. Those are conversations, and you can have one with us without it turning into a sales call.
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