I’m over 65 and retiring. Now what? |

Five things, then two more to know.

1. Don’t let COBRA fool you

If COBRA paperwork is already sitting in front of you, read this part before you sign anything.

COBRA doesn’t count as employer coverage for Medicare’s purposes. Neither does retiree coverage or severance. Your Medicare clock starts the day the job ends, not the day COBRA runs out.

People take COBRA because it feels like the same plan continuing — and coverage-wise, it is. But once you’re Medicare-eligible and the job has ended, the rules change. COBRA doesn’t hold your Medicare window open. Run it out and you can end up with a penalty that never goes away, plus months with no coverage at all before Medicare can start.

For the record, we think that rule is stupid. But the rules are the rules.

Everything else on this page can be fixed after the fact. This one can’t.

2. Pick your date and tell Medicare what it is

The day your group coverage ends and the day Medicare starts should be the same day. You get to make that happen — but only if you file while you’re still covered.

While you’re still on the group plan, the enrollment form lets you name your own start date: the month you file, or the first of any of the next three months. You write it on the form. That’s how you land Medicare the day your employer plan drops off, with no gap and no month of paying for both.

Wait until after you’ve left and you lose that. Part B simply starts the month after Social Security gets your paperwork, and whatever gap falls out of that is yours to cover.

You do have eight months after the job ends before any penalty attaches. Treat that as the outer limit, not the plan.

3. Get the two forms

CMS-40B — Application for Enrollment in Medicare Part B.

You complete this one. The start date you picked in step 2 goes in the remarks section.

CMS-L564 — Request for Employment Information.

Your employer completes this one. It proves you had group coverage the whole time you were working, and it’s what waives the late enrollment penalty.

Call us at 281-894-7540 and we’ll send you both forms, already filled in as far as we can take them. It takes us five minutes and saves you the hunt.

Or get them yourself — both are free at cms.gov. You can start the application through Social Security’s online tool for this exact situation and upload the rest, or send everything by mail or fax to your local office. Online is the fastest.

The L564 is the piece that sits in somebody’s HR inbox for three weeks, so ask early. And yes — asking HR to verify your coverage history tends to announce that you’re leaving. If that’s awkward where you work, the timing is worth a conversation before you start.

If your employer won’t sign it, you’re not stuck. Companies close, merge, or simply don’t answer. Social Security accepts other proof. Call us at 281-894-7540 and we’ll tell you exactly what to send. A missing signature is not a penalty.

4. Decide how you’ll cover the 20% — THIS IS THE IMPORTANT ONE

The rest of this page is paperwork and deadlines. This is the decision you actually live with, and it shapes how Medicare goes for you for years.

Two common ways: a Medicare supplement with a separate drug plan, or a Medicare Advantage plan with drug coverage built in.

Which one fits depends on how you want to receive care and what you want to spend. That’s a conversation, not a web page.

Call us at 281-894-7540 and we’ll walk through both.

5. Watch the two-month drug deadline

You have eight months to enroll in Part A and Part B. You have two months for drug coverage.

Miss the shorter one and you’ll carry a penalty on your drug premium for as long as you have it. People hear “eight months,” never hear the other number, and find out years later when they finally need a medication.

Two more things to know before you set a date

Who else is on your plan

A spouse, a dependent, anyone covered through your job — they lose that coverage the day you do, and Medicare doesn’t cover them.

If they’re under 65 they’ll need somewhere to go, and COBRA is a perfectly good option for them. The warning at the top of this page was about you: COBRA is dangerous because it doesn’t hold your Medicare window open. Someone who isn’t Medicare-eligible has no window to protect, so the risk doesn’t apply.

It’s still a separate decision with its own deadlines, and it’s the one people find out about two weeks too late.

IRMAA

If your income is above a certain level, Medicare adds a surcharge to your Part B and drug premiums. It’s called IRMAA — the Income-Related Monthly Adjustment Amount — and it’s set from your tax return from two years ago.

This affects roughly 8% of people on Medicare, so it may well not be you. But if you’re a higher earner it’s worth knowing ahead of time, because the return Medicare looks at is from back when you were still working. The lag doesn’t clear in a year, either — it’s recalculated annually, always two years behind, so a retiree can see the surcharge for a couple of years running on income they no longer have.

CMS publishes the current income brackets and amounts here:

2026 Medicare Parts A & B Premiums and Deductibles

The fix is Form SSA-44, Medicare Income-Related Monthly Adjustment Amount — Life-Changing Event. Retirement counts as a life-changing event. You file it, you show what you actually make now, and Social Security prices you on that instead of waiting for the lookback to catch up.

It works. It just doesn’t happen automatically, and nobody mails you a reminder — so if your income changed, appeal.

Then get on with it

That’s the whole process. Most people are through it in a couple of conversations.

Call us at 281-894-7540 two or three months before your last day and we’ll make sure it’s done right — COBRA handled before it costs you, start date elected instead of assigned, both forms filed, drug coverage inside its window, IRMAA appealed if it applies, and your household sorted out.

None of this is hard. It’s just unforgiving, and most of it can only be fixed before it happens.

We’ll be as involved as you want us to be. No obligation, and our services are always free to you.

Not connected with or endorsed by the United States government or the federal Medicare program.

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I’m over 65 and retiring. Now what?