Initial Enrollment Period · National guide

Turning 65? Here is exactly what to do about Medicare

Your Initial Enrollment Period is 7 months: the 3 months before the month you turn 65, your birthday month, and the 3 months after. Enroll in the first 3 months to avoid coverage gaps and the Part B late penalty, which is 10% of the premium for every year you delay, charged permanently. The seven steps below cover every scenario.

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Christian Brinkley, licensed insurance agent in Greensboro, North Carolina
Christian BrinkleyNC Life & Health · Greensboro, NC
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By Christian Brinkley, NC Life & Health · Updated October 2026

The seven steps, in order

  1. 1

    Find your 7-month Initial Enrollment Period

    Your window covers the 3 months before the month you turn 65, your birthday month, and the 3 months after. If your birthday falls on the first of the month, the window shifts one month earlier.

  2. 2

    Enroll in the first 3 months for on-time coverage

    Enrolling before your birthday month generally means Part B starts the month you turn 65. Enrolling during or after the birthday month usually delays your start date by one or more months.

  3. 3

    Decide about Part B if you are still working

    If you have group health coverage based on current employment (yours or your spouse's), you can usually delay Part B without penalty and enroll later through a Special Enrollment Period. Retiree coverage and COBRA do not qualify. If you contribute to an HSA, do not enroll in any part of Medicare, including premium-free Part A.

  4. 4

    Mark your 6-month Medigap window separately

    Medigap open enrollment starts the first month you are 65 or older and enrolled in Part B, and lasts 6 months. During this window, insurers cannot deny you a policy or charge more based on health. This protection is generally a one-time event.

  5. 5

    Compare your coverage options

    Original Medicare plus Medigap plus a Part D drug plan, or a Medicare Advantage plan that bundles hospital, medical, and usually drug coverage. Compare using your doctors, your prescriptions, and your budget, not just the premium.

  6. 6

    Apply through Social Security

    Enroll in Parts A and B through Social Security: online at ssa.gov, by phone at 1-800-772-1213, or in person at a local office. If you are already receiving Social Security benefits, you are enrolled automatically.

  7. 7

    Confirm everything before your start date

    Check that your doctors accept your coverage, your prescriptions are on the plan's formulary, and your cards have arrived. Fix problems before your coverage starts, not after.

Which situation sounds like you?

The rules change based on your situation. Find yours below.

Still working with employer coverage

If your employer has 20 or more employees and your coverage is based on current employment, you can usually delay Part B without the late penalty. When that job or coverage ends, you get an 8-month Special Enrollment Period to sign up for Part B. You will need Form CMS-40B (the Part B application) and Form CMS-L564 (proof of employer coverage, signed by your employer). Part A is usually premium-free, but if you contribute to an HSA, enrolling in Part A ends your eligibility to contribute.

On Medicaid

If you have full Medicaid when you turn 65, you generally must enroll in Medicare. Medicaid may continue as secondary coverage, paying costs Medicare does not. You may also qualify for a Medicare Savings Program. Do not assume Medicaid alone is enough: check with your state Medicaid office about how the two work together in your case.

Self-employed or no employer coverage

Without group coverage based on current employment, there is no penalty-free way to delay. Enroll in the first 3 months of your Initial Enrollment Period so coverage starts on time. Individual marketplace plans do not count as creditable coverage for delaying Part B.

On disability (under 65)

If you have received Social Security disability benefits for 24 months, you are automatically enrolled in Medicare regardless of age. The turning-65 rules above do not apply, but you get a second Initial Enrollment Period at 65 with fresh Medigap protections in most states.

Key numbers to know

Figure2026
Part B standard premium$202.90 / month (CMS)
Part B annual deductible$283 (CMS)
Part B late penalty10% of premium per 12 months delayed, permanent
Initial Enrollment Period7 months around your 65th birthday

Sources: CMS.gov, Medicare.gov enrollment, SSA.gov.

Common questions

What is the Part B late enrollment penalty?
10% of the standard Part B premium for every full 12 months you were eligible but did not enroll, charged for as long as you hold Part B. It is permanent. With the 2026 standard premium at $202.90 a month, a one-year delay adds about $20 a month to your premium for life.
What forms do I need to enroll in Part B if I delayed?
Form CMS-40B, the Application for Enrollment in Medicare Part B, and Form CMS-L564, the Request for Employment Information, which your employer signs to prove you had group coverage based on current employment. Submit both to Social Security when your employer coverage ends.
Can I contribute to an HSA after enrolling in Medicare?
No. Once you enroll in any part of Medicare, including premium-free Part A, you can no longer contribute to a Health Savings Account. If you are still working and contributing to an HSA at 65, delay all Medicare enrollment until you stop contributing.
What is the difference between my Initial Enrollment Period and Annual Enrollment?
Your Initial Enrollment Period is based on your 65th birthday and is when you first join Medicare. Annual Enrollment, October 15 through December 7 each year, is for people already on Medicare to review or change Medicare Advantage and Part D plans. They are separate windows with separate rules.
Do I have to sign up for Medicare at 65 if I am still working?
Not necessarily. If you have group health coverage based on current employment from an employer with 20 or more employees, you can usually delay Part B without penalty. You get a Special Enrollment Period when that coverage ends. Retiree plans and COBRA do not qualify for the delay.
When does my Medigap open enrollment period start?
The first month you are 65 or older and enrolled in Part B. It lasts 6 months. During this window, insurers must sell you any Medigap policy they offer without medical underwriting. Outside this window, they can deny coverage or charge more based on your health in most states.
Where do I actually sign up for Medicare?
Through Social Security: online at ssa.gov, by phone at 1-800-772-1213, or in person at a local Social Security office. If you already receive Social Security benefits, enrollment in Parts A and B is automatic.

Already on Medicare? Read the annual enrollment guide. Comparing coverage types? See Advantage vs. Medigap. In the Piedmont Triad, the local turning-65 page has Greensboro-specific resources.

Before you compare plans, get your doctors, prescriptions and pharmacy onto one page. The Annual Enrollment checklist lists ten things to review and where to find each one.

Christian Brinkley, licensed insurance agent in Greensboro

Christian BrinkleyNC Life & Health · Greensboro, NC

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By Christian Brinkley, Licensed NC Insurance Agent (NPN 22217190). Last updated October 2026.

Sources: Medicare.gov, CMS.gov, SSA.gov

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