Turning 65
Turning 65: what to do, and the order to do it in
Figures on this page checked . Medicare and marketplace numbers reset every year — if you are reading this long after that date, call and we will tell you what moved.
The two windows, and why people confuse them
Nearly every mistake we see at 65 comes from treating these as one window. They start at different moments and they punish you in different ways.
- Your Initial Enrollment Period — 7 months. Three months before your birthday month, the month itself, three months after. Miss it without employer coverage and Part B costs you 10% of the standard premium for each full 12 months you could have had it and did not — for the rest of your life.
- Your Medigap Open Enrollment Period — 6 months. It starts the first day you are both 65 or older and enrolled in Part B. Inside it, no carrier can ask a health question. Once it closes, in Colorado, they can.
Read the second one again. It starts when you enroll in Part B, not when you turn 65. If you delay Part B because you are still working, your Medigap window has not opened yet — it waits for you. That is the single most useful sentence on this page for anyone still employed.
Five steps, and the order matters
Start about four months before your birthday month. Nothing here takes long; the sequence is what matters.
- First, settle the employer question. Are you or your spouse covered by a plan through a job somebody currently holds, and does that employer have twenty or more employees? That answer has a big impact on the next steps.
- Second, stop health savings account contributions if you have one. Six months before you apply, not the month you apply. The reason is below.
- Third, enroll in Part A and Part B through Social Security — unless the employer answer in the first step told you to delay Part B. Do this early in your window, not late.
- Fourth, choose your road: a Medicare Supplement policy with a separate Part D plan, or a Medicare Advantage plan. This is the decision the Medigap window is counting down on.
- Fifth, check your prescriptions against the drug list of whatever you are about to buy. Every year. This is the step people skip and regret.
If you already draw Social Security retirement or disability income, step three happens without you — Parts A and B start automatically and a card arrives in the mail. While convenient, it is also how some people end up enrolled in Part A without meaning to be, and that can have unintended consequences.
If you are still working
You can usually delay Part B with no penalty, provided the coverage comes from a job somebody currently holds and the employer has twenty or more employees. Most people take Part A anyway, because it usually costs nothing.
Two situations where taking Part A is wrong
If you contribute to a health savings account, Part A ends that. And if your employer has fewer than twenty employees, Medicare generally becomes your primary insurance at 65 whether you signed up or not, so delaying Part B can leave you paying most of your own claims.
When the job ends, an 8-month Special Enrollment Period opens — and it starts when the employment or the group plan ends, whichever comes first. COBRA does not extend it.
The forms and the sequence for that transition are on their own page, because there are two of them and one needs your employer’s signature.
The health savings account rule that catches people
Read this one even if you think it does not apply to you. It arrives as a tax bill a year later, which is far too late to fix cheaply.
When you apply for Medicare at or after 65, Part A can be backdated up to 6 months — never earlier than the first month you were eligible, but up to six months back. Meanwhile the IRS is clear that your health savings account contribution limit is zero for any month you are enrolled in Medicare.
What that combination does
Contributions you made in those backdated months become excess contributions. The IRS charges 6% on the excess for each year it stays in the account. You did nothing wrong at the time and the penalty applies anyway.
The prevention is simple: stop contributing six months before you apply for Medicare or Social Security. If you have already contributed past that point, there is a way to withdraw the excess before your filing deadline and avoid the excise tax.
We advise on insurance, not on taxes, and this is a question for whoever prepares your return. What we can do is tell you the date your six months starts counting back from, which is the piece of information you need to avoid or correct the mistake.
Medigap or Advantage: the decision the clock is on
Original Medicare pays 80% of covered Part B costs after the deductible and has no annual limit on the other 20%. Closing that hole is what both roads do, in different ways.
- Medicare Supplement (Medigap): higher monthly premium, predictable costs when you use care, any provider in the country who accepts Medicare, a separate Part D plan.
- Medicare Advantage: lower or no additional premium, a network, an annual out-of-pocket cap, and drug coverage usually included.
The primary reason to decide this now rather than later is that you can join an Advantage plan at almost any point in the future without answering a health question. Going the other direction — from Advantage to Medigap, after your six months have closed — means answering health questions, and a Colorado carrier can decline you.
We will help you work out which path is right for you and be straight about all of your options — including when Advantage is the better answer, and for plenty of people it is. We would rather lose the sale than put you in a Medigap premium you stop being able to afford at 78.
Questions about turning 65
When should I start dealing with this?
About four months before your birthday month. That puts you at the start of your seven-month enrollment window rather than the end of it, which is where coverage gaps come from.
If you have a health savings account, start earlier — six months before you plan to apply, because Part A backdates up to six months and your contribution limit for those months becomes zero.
Am I enrolled automatically?
Only if you are already receiving Social Security or Railroad Retirement benefits when you turn 65. In that case Parts A and B start on their own and a card arrives in the post.
Everyone else has to sign up, and Social Security is who you sign up with — not us, and not Medicare directly. We can tell you what to do and in what order, but the enrollment itself is yours to submit.
Do I need a Part D plan if I take no prescriptions?
Usually yes, and this is one of the more common expensive decisions we see. Part D has its own late enrollment penalty, it is calculated per month you went without, and it is permanent once it attaches.
Going without is defensible only if you have other drug coverage that Medicare considers at least as good — coverage from a current employer, or from the VA, for instance. Your plan has to tell you in writing whether it counts. Keep that letter.
Can I start with Advantage and switch to Medigap later?
You can try, and in Colorado a carrier can say no. Once your six-month Medigap window closes, carriers are allowed to ask health questions, charge you more, or decline you outright. Colorado has no birthday rule and no annual guaranteed-issue window.
A couple of exceptions exist and both run on a twelve-month clock. If Medicare Advantage is the first thing you ever choose on Medicare and you leave it within a year, you can buy any supplement policy from any carrier, no health questions. And if you drop a Medigap policy to try Advantage for the first time and come back within the year, you can have your old policy back from the same carrier if they still sell it.
Both are one-time opportunities rather than a general escape, and neither can be used again — after two years from that first enrollment, nothing counts as a trial any more. If you took an Advantage plan last autumn, the date to know is twelve months from when it started.
CMS-required disclaimer
We do not offer every plan available in your area. Currently we represent 7 organizations which offer 45 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all of your options.