Medicare eligibility, enrollment windows, and what happens if you miss them — explained in plain language.
It depends on your situation. Find yours below.
You are turning 65 and not working
Yes — enroll during your Initial Enrollment Period (IEP). Missing it can mean permanent penalties.
What to do: Enroll in Parts A and B during your 7-month IEP window.
How to Enroll at 65You are turning 65 and still working at a company with 20+ employees
You can delay Medicare without penalty as long as you have active employer group coverage. Part A is usually free, so many people take it anyway.
What to do: Confirm your employer plan is creditable for Part D. Call Fred to compare costs.
Considerations Before 65You are turning 65 and work for a small employer (fewer than 20 employees)
Yes — you need Medicare. Medicare becomes primary payer for small employers, so you must enroll in both Part A and Part B.
What to do: Enroll during your IEP. Do not delay.
How to Enroll at 65You are already receiving Social Security benefits
You will be automatically enrolled in Parts A and B. Watch for your red, white, and blue Medicare card in the mail.
What to do: Review your card when it arrives. If you have employer coverage, you can decline Part B — but call Fred first.
How to Enroll at 65You are on an ACA / Marketplace plan
Yes — you must enroll in Medicare at 65. ACA/Marketplace coverage is not coverage based on current employment, so it does not give you a Special Enrollment Period to delay Part B. Your ACA subsidy also ends when you become Medicare-eligible.
What to do: Enroll during your IEP. For Part D, ask your Marketplace plan administrator whether the prescription drug coverage is creditable before assuming you can delay Part D enrollment.
How to Enroll at 65You are on COBRA
COBRA is not coverage based on current employment, so it does not qualify as employer group health coverage for Part B Special Enrollment Period purposes. In most cases you should enroll in Medicare and use COBRA as secondary — or drop COBRA entirely.
What to do: For Part D, ask your COBRA plan administrator whether the prescription drug coverage is creditable. Read the COBRA & Medicare FAQ or call Fred before making any decisions.
COBRA & Medicare FAQNot sure which situation applies to you? Call Fred at 763.292.9837 — it's a free conversation with no obligation.
Six things that catch people off guard — and how to avoid them.
Your Initial Enrollment Period (IEP) is 7 months
It starts 3 months before your 65th birthday month, includes your birthday month, and ends 3 months after. Enroll as early as possible — waiting until after your birthday month can delay when your coverage starts.
Part A is usually free; Part B has a monthly premium
Most people pay $0 for Part A (hospital) if they or their spouse worked and paid Medicare taxes for at least 10 years. Part B (medical) has a standard premium of $202.90/month in 2026. Higher-income beneficiaries pay more due to IRMAA.
Original Medicare alone leaves significant gaps
Original Medicare helps pay for Medicare-covered hospital and medical services, but it does not pay all of the costs. You remain responsible for applicable deductibles, coinsurance and other cost sharing, and Original Medicare does not have an annual out-of-pocket maximum. A Medicare Supplement plan can help pay some of the out-of-pocket costs for Medicare-covered services that Original Medicare does not pay.
HSA and Medicare enrollment require special planning
If you have a Health Savings Account (HSA), Medicare enrollment requires special planning. You cannot contribute to an HSA for any month you are enrolled in Medicare. If you enroll in premium-free Medicare Part A after age 65, Part A coverage may be retroactive for up to six months, but not earlier than the first month you were eligible for Medicare. If you apply for Medicare six or more months after turning 65, you should generally stop HSA contributions six months before the month you apply. If you enroll around age 65, different timing rules apply. Your last HSA contribution should generally be made before your Medicare Part A coverage begins.
Drug coverage (Part D) has its own late penalty
If you go 63 or more consecutive days without creditable drug coverage after your IEP ends, you will pay a permanent Part D late enrollment penalty for as long as you have Medicare. Enroll in a Part D plan even if you take no medications.
Medigap open enrollment is a one-time window
The 6-month Medigap Open Enrollment Period starts when you are both 65 and enrolled in Part B. During this window, insurers cannot deny you coverage or charge more due to health conditions. After it closes, you may face medical underwriting.
Want the full checklist?
The Considerations Before 65 page covers employer coverage, HSA rules, and how to time your enrollment to avoid penalties.
Read: Considerations Before You Turn 65Five steps from eligibility to full coverage.
Enroll in Parts A and B
Apply online at SSA.gov, call Social Security at 1-800-772-1213, or visit your local Social Security office. Apply up to 3 months before your birthday month for coverage to start on time.
How to enroll at 65Choose how to get your coverage
Decide between Original Medicare + Supplement + Part D, or Medicare Advantage (which bundles everything). Each path has trade-offs in cost, flexibility, and network access.
Compare your optionsEnroll in a Part D drug plan
Even if you take no medications, enroll in a low-cost Part D plan to avoid the late enrollment penalty. You can always switch plans during AEP each fall.
Learn about Part DConsider dental and vision coverage
Original Medicare does not cover routine dental or vision care. Standalone dental and vision plans are available and affordable.
Dental insurance optionsTalk to Fred
A licensed local agent can compare every plan available in your zip code, explain the trade-offs in plain language, and help you enroll — at no cost to you.
Fred Lang is a licensed Medicare agent in Minnetrista, MN. He'll walk you through your options at no cost to you — no pressure, no sales pitch.