Turning 65: the Medicare playbook

1. 1

   Seven months before your birthday

   Learn what each part of Medicare does

   Part A is the hospital, Part B is the doctor, Part D is the pharmacy, and Part C is a private plan that bundles A and B. Every later decision uses this vocabulary, so learn it before the mail starts arriving.

   • Medicare Parts A, B, C, and D — What They Actually Cover
   • Medicare Basics
2. 2

   Six months before

   Decide what happens to your work coverage

   If you or your spouse will keep working past 65 with coverage from a larger employer, you may be able to delay Part B without a penalty. If the employer is small, or the coverage is COBRA or a retiree plan, you usually cannot. Settle this first, because it changes every date below.

   • Still Working at 65? How Your Employer Insurance Works With Medicare
   • Employer coverage vs Medicare at 65
   • COBRA vs Medicare
   • Working Past 65? When to Delay Medicare Enrollment
3. 3

   Three months before — your window opens

   Know your Initial Enrollment Period

   Your first window runs seven months: the three before your birthday month, the month itself, and the three after. Enrolling in the first three means coverage starts the month you turn 65; enrolling later delays it. Put the dates on a calendar now.

   • Medicare Enrollment Periods: Don't Miss These Deadlines
   • Enrollment Timeline
   • Enrollment Periods
4. 4

   Three months before

   Choose your path: Original Medicare with Medigap, or Medicare Advantage

   This is the fork. One path buys freedom of choice and predictable costs for a higher monthly premium; the other buys a lower premium and bundled extras for a network and approval rules. One of the two is much harder to reverse later, so decide it with the comparison, not the commercial.

   • Medigap vs Medicare Advantage
   • Medicare Advantage vs Original Medicare
   • Choosing Your Medicare Path: Medigap vs. Medicare Advantage
5. 5

   Two months before

   Cover your prescriptions

   Part D is separate unless your Advantage plan includes it. Compare plans on the drugs you actually take, at the pharmacy you actually use — and enroll even if you take nothing today, because the penalty for waiting is permanent.

   • Medicare and Prescriptions: How Part D Drug Plans Work
   • Part D vs Medicare Advantage drug coverage
   • Part D Prescription
6. 6

   Two months before

   Know what it will cost — and what help exists

   Part B has a monthly premium that rises with income; Part D plans and Medigap add their own; each part has cost-sharing. Extra Help and Medicare Savings Programs cover some of it for people with limited income. Run the numbers for your situation before you commit.

   • How Much Does Medicare Cost in 2025? The Real Numbers
   • Medicare Cost Estimator
   • Extra Help Screener
   • Costs & Savings
7. 7

   Your birthday month

   Sign up

   If you already receive Social Security, Parts A and B arrive automatically; if not, you apply through Social Security yourself. Advantage, Part D and Medigap are each a separate enrollment with the plan. Keep every confirmation.

   • Your Guide to Signing Up for Medicare: A Step-by-Step Approach
   • Turning 65? Here's Exactly What You Need to Do About Medicare
8. 8

   Your first months on Medicare

   Settle in and avoid the expensive mistakes

   Cards arrive, the first bills arrive, and the fall enrollment period comes around faster than you expect. Check that every provider you use is in network or accepts Medicare, set up premium payments, and note the dates you can change plans if the first choice was wrong.

   • Starting Medicare: Essential Steps for Your First Month
   • 5 Expensive Medicare Mistakes People Make (And How to Avoid Them)
   • Life at 65

• Assuming employer coverage, COBRA or a retiree plan lets you skip Part B. Only current employment at a larger employer does, and the rules are specific.
• Waiting for a letter. If you are not already receiving Social Security, nobody enrolls you — you start the application yourself.
• Choosing a plan by its premium alone. A low monthly cost buys a network and approval rules; whether that trade is right for you depends on how you use care.
• Skipping drug coverage because you take nothing today. The late-enrollment penalty is permanent and grows every month you wait.
• Missing the Medigap open-enrollment window. In most states it is the one time a Medigap insurer cannot ask about your health.

Every topic on this page has a hub with its guides, comparisons and videos. Start with the one your question belongs to.