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Home / Turning 65: Your Medicare Checklist

Turning 65: Your Medicare Checklist

Your 65th birthday opens a seven-month window that decides more than most people realize — including the only guaranteed chance to buy a Supplement without health questions. Here is what to do and when.

Find My Medicare Dates

Enter your date of birth and we'll show your effective date, your Initial Enrollment Period and your Medigap open-enrollment window.

Your Initial Enrollment Period

You can sign up for Medicare during the 7-month window around your 65th birthday month (3 months before, your birthday month, 3 months after). Enroll in the three months before your birthday month and coverage starts the first day of your birthday month (the month before if your birthday is on the 1st). Enroll later in the window and coverage starts the month after you sign up.

The Checklist

  1. Four to six months out — decide about Part B. If you (or your spouse) are still working and covered by an employer plan with 20 or more employees, you can usually delay Part B without penalty. With fewer than 20 employees, Medicare becomes primary at 65 and you generally need Part B. Retiree plans and COBRA do not count as active employer coverage. This single decision is where the most expensive mistakes happen — ask us.
  2. Three months out — enroll in Part A and B at ssa.gov, by phone with Social Security, or in person. If you already receive Social Security, you'll be enrolled automatically and your card arrives by mail.
  3. Three months out — choose your path. Medicare Advantage, or a Supplement plus Part D. Your six-month Medigap Open Enrollment window starts when you're 65 and enrolled in Part B; no insurer can decline you or charge more for health during it.
  4. Two months out — price your prescriptions. Whichever path you choose, we run your exact medication list against the drug coverage available in your county.
  5. One month out — enroll in your plan. Advantage, Medigap and Part D applications can all be submitted before your Medicare effective date so there's no gap.
  6. Fill the gaps. Supplement users usually add dental, vision and hearing; Advantage users often add a hospital indemnity plan to cover copays.
  7. Keep creditable drug coverage. Going 63+ days without it after your window ends triggers a permanent Part D penalty.

What Medicare Costs in 2026

  • Part A: $0 premium for most people who worked 10+ years; $1,736 inpatient deductible per benefit period.
  • Part B: $202.90 standard monthly premium (higher at higher incomes, based on your tax return from two years ago); $283 yearly deductible; then 20% of most services.
  • Part D: premiums vary by plan; $2,100 yearly cap on covered drug costs.

Common Turning-65 Situations

  • Still working, large employer: most people take Part A (it's premium-free) and delay Part B; HSA contributors should know Part A enrollment ends HSA eligibility.
  • Spouse's plan: the same 20-employee rule applies to the spouse's employer.
  • Retiring at 65: enroll in Part B now; when employer coverage ends you'll get an 8-month Special Enrollment Period, but the Medigap guaranteed window is only 63 days after the employer coverage ends.
  • Under 65 on disability: Medicare starts automatically after 24 months of disability benefits; Medigap rights before 65 vary by state.

Common Questions

When should I sign up for Medicare if I'm turning 65?

Your Initial Enrollment Period is the 7 months around your 65th birthday month. Sign up in the 3 months before it for coverage on the first day of your birthday month. If you're still working with employer coverage from an employer with 20+ employees, you can usually delay Part B without penalty.

Do I have to take Medicare at 65 if I'm still working?

Not necessarily. With active employer coverage from an employer with 20 or more employees, you can delay Part B penalty-free and enroll later with a Special Enrollment Period. With fewer than 20 employees, Medicare is primary and you generally should enroll. COBRA and retiree coverage don't count.

What happens if I miss my Initial Enrollment Period?

You can enroll during the General Enrollment Period (January 1 – March 31) with coverage starting the month after you sign up, and you may owe a Part B late-enrollment penalty of 10% for each full 12-month period you could have had Part B but didn't — for as long as you have Part B.

Do I need to sign up for Medicare if I get Social Security?

If you already receive Social Security or Railroad Retirement benefits, you're enrolled automatically in Parts A and B and your card arrives about 3 months before your 65th birthday. You can decline Part B if you have active employer coverage.

Rules and amounts above come from Medicare.gov and CMS for the 2026 plan year and the 2027 landscape release. Plans, benefits and premiums vary by county and change each year — confirm details with the plan or with a licensed agent before enrolling.

Important: We do not offer every plan available in your area. Currently we represent 17 organizations which offer — products in your area (). Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

Organizations we represent: Aetna (CVS Health) · Clover Health · Devoted Health · Elevance Health (Anthem / Simply Healthcare) · Florida Blue · Freedom Health · HCSC · Cigna Healthcare (HealthSpring) · HealthSun · Humana · Kaiser Permanente · Molina Healthcare · Optimum Healthcare · Prominence Health · UnitedHealthcare · Wellcare · Zing Health. Availability varies by county.

Vitality Health Advisors is a licensed, independent insurance agency, not connected with or endorsed by the United States government or the federal Medicare program. Enrollment in a plan depends on the plan's contract renewal with Medicare. Benefits, premiums, provider networks and drug formularies vary by plan and county and may change each year. This is a solicitation of insurance. Information you submit on this site will be provided to a licensed insurance agent for future contact. Calls to and from our agents are recorded. Statistics cited on this site are from the CMS 2027 Medicare Advantage and Part D Landscape fact sheets (September 28, 2026) unless otherwise noted.