Turning 65: your Medicare enrollment checklist

Turning 65 puts you at the front door of Medicare, and the decisions you make in the months around your birthday can affect your coverage and costs for years. The good news: the process is manageable once you understand three things — your enrollment window, whether your current coverage changes anything, and which path you want for your benefits. This checklist walks through each one.

As always, this is general education rather than personalized advice. Deadlines and rules have exceptions, so confirm your specific situation with Medicare.gov, 1-800-MEDICARE, your benefits administrator at work, or a licensed insurance agent.

Know your Initial Enrollment Period

Your Initial Enrollment Period (IEP) is a seven-month window built around your 65th birthday: it begins three months before your birthday month, includes your birthday month, and ends three months after it. During this window you can enroll in Part A, Part B, a Medicare Advantage plan, and a Part D drug plan.

Timing within the window matters. If you sign up in the three months before your birthday month, coverage generally starts the first day of your birthday month. If you wait until your birthday month or later, your start date is pushed back. If you are already receiving Social Security benefits, you will usually be enrolled in Parts A and B automatically and will receive your Medicare card in the mail — but you still need to make decisions about drug coverage and any additional plan.

Still working at 65? Read this first

If you (or your spouse) are still working and you are covered by an employer group health plan from an employer with 20 or more employees, you can usually delay Part B without penalty while that coverage lasts. Many people in this situation enroll in premium-free Part A and delay Part B. One important exception: if you contribute to a Health Savings Account (HSA), enrolling in any part of Medicare — including Part A — ends your eligibility to contribute, so plan the timing carefully.

When that employment or coverage ends, you get an eight-month Special Enrollment Period to sign up for Part B without penalty. COBRA and retiree coverage do not count as current employer coverage for this purpose — a common and expensive misunderstanding. If your employer has fewer than 20 employees, Medicare generally becomes your primary coverage at 65 and you usually should not delay Part B. Confirm with your benefits administrator either way.

The penalties you are trying to avoid

The Part B late-enrollment penalty adds 10 percent to your premium for each full 12-month period you could have had Part B but did not sign up — and it lasts for as long as you have Part B. The Part D penalty works differently: roughly 1 percent of the national base premium for each month you went without creditable drug coverage, also added for as long as you have drug coverage.

Both penalties are completely avoidable with on-time enrollment or documented creditable coverage. Keep any “creditable coverage” notices your employer or plan sends you; they are your proof if questions come up later.

Choose your coverage path

With Parts A and B in place, you face the main fork in the road. Option one is Original Medicare, usually with a standalone Part D drug plan, and often a Medicare Supplement (Medigap) policy. A key fact many people learn too late: your strongest right to buy a Medigap policy without health questions is the six-month window that starts when you are 65 or older and first enrolled in Part B. After that window, insurers in most states can consider your health.

Option two is a Medicare Advantage plan, which bundles your benefits through a private plan, often with drug coverage and extra benefits, in exchange for a provider network and plan rules. Compare both paths against your doctors, prescriptions, budget, and travel before deciding — not just the monthly premium.

Your 90-day countdown checklist

Three months out: confirm how you will enroll (automatic via Social Security, or yourself at ssa.gov), ask your employer about creditable coverage if you are still working, and list your doctors and prescriptions. Two months out: compare the Original Medicare path versus Medicare Advantage plans available in your county, check that your medications appear on any drug plan's formulary, and decide whether a Medicare Supplement policy fits your budget.

One month out: complete your enrollments, note your coverage start dates, and set a calendar reminder for the fall Annual Enrollment Period (October 15 to December 7) when you can review and change drug or Advantage coverage each year. If you would like help comparing the plans available where you live, a local licensed agent can walk through the options they represent at no cost to you — search your ZIP code in our directory to find one.

Frequently asked questions