Turning 65 in 2026: Your Complete Medicare Enrollment Checklist

Quick Medicare Enrollment Checklist (if no work insurance beyond 65)*

☐ 6 months out: Consider stopping HSA contributions (if you have one)

☐ 3 months out: Apply for Medicare Part A and B at ssa.gov

☐ 2 months out: Research Original Medicare + Medigap + Part D, vs. Medicare Advantage

☐ 1 month out: Confirm your Medicare Part A and B start dates

☐ 1 month out: Apply for Medigap + Part D or Medicare Advantage

☐ At 65: Your Medicare and supplemental insurance starts the first of the month you turn 65!

*Working past 65? See section below to confirm you are eligible to delay Medicare Part B.

OVERVIEW: How the 7-Month Medicare Initial Enrollment Period Works

When you turn 65, you get a 7-month Initial Enrollment Period (IEP) to sign up for Medicare Parts A and B. That window opens 3 months before your birthday month, includes the month you turn 65, and closes 3 months after. It doesn’t automatically extend, and it doesn’t come around again.

Timing matters inside the IEP. If you enroll during the first 3 months (before your birthday month), your Part B coverage starts the month you turn 65. If you wait until your birthday month or later, coverage is delayed by at least one month. Enrolling early within your window gives you the cleanest and earliest start date. This will help you avoid any gap in coverage.

If you’re already collecting Social Security retirement benefits, you’ll be enrolled in Parts A and B automatically — your red, white, and blue Medicare card arrives in the mail a few months before your 65th birthday. You don’t need to do anything to get enrolled, but you still need to make supplemental insurance decisions once you have it.

Medicare Costs: Most people get Part A (hospital insurance) at no premium if they or their spouse paid Medicare taxes for at least 40 quarters. Part B (medical insurance) carries a standard monthly premium of $202.90 in 2026, deducted automatically from your Social Security check if you’re already receiving benefits. The Part B annual deductible is $283. Higher-income beneficiaries pay more through IRMAA surcharges and can expect a higher Part B premium. Learn more here: Social Security Administration, Medicare (Publication No. 05-10043), 2026.

6 Months Before Your 65th Birthday

☐ Consider Stopping Contributions to Your HSA

If you have a Health Savings Account (HSA) through a high-deductible employer plan, consider stopping contributions at least 6 months before you plan to enroll in Medicare. This matters because Medicare Part A coverage can be backdated up to 6 months when you apply — and the IRS prohibits HSA contributions once any part of Medicare is in effect. Contributing after your Medicare start date may trigger a tax penalty. Source: Social Security Administration, Medicare (Publication No. 05-10043).

Note: This is general publicly available information and is not tax nor financial advice. Please consult your tax or financial advisor before making changes to your HSA.

3 Months Before Your 65th Birthday

☐ Sign Up for Medicare Part A and Part B

If you’re not already receiving Social Security benefits, you need to actively enroll. The Social Security Administration handles enrollment for Original Medicare (Parts A and B). Apply online at ssa.gov or call Social Security at 1-800-772-1213. Applying 3 months before your birthday month ensures your coverage starts the month you turn 65 with no gap.

What you’ll need: your Social Security number, date and place of birth, and if you have current employer group health coverage, the start and end dates for that plan. So just to be clear, you have to go to Social Security Administration to sign up for Medicare (not Medicare.gov!).

2 Months Before Your 65th Birthday

☐ Decide Between Original Medicare + Medigap + Part D, or Medicare Advantage

The choice you’ll make at 65 has long-term consequences. There are two paths:

• Original Medicare (Parts A + B) + Medigap + Part D — You have Medicare as your primary insurance and add a Medigap (Medicare Supplement) plan to cover most of what Medicare doesn’t. This combination typically means no network restrictions, predictable out-of-pocket costs, and coverage anywhere in the country that accepts Medicare. Learn more about Medigap here
• Medicare Advantage (Part C) — A private plan that bundles Parts A and B (and usually Part D) with extra benefits. Lower premiums in many cases, but network restrictions, prior authorization requirements, and variable out-of-pocket exposure. Learn more about Medicare Advantage here

Note: We typically don’t sell Medicare Advantage at Senior65. We believe Medigap is a superior long-term product for most seniors who can afford it — and we’re upfront about that. You can read a full comparison of your options at our New to Medicare guide.

1 Month Before Your 65th Birthday

☐ Confirm Your Medicare Part A and B Start Dates

If you have followed this checklist you should have received your red, white and blue Medicare card in the mail. It will show your Medicare number and your Part A and Part B Effective (start) dates. If you haven’t received the card yet, log on to SSA.gov and click on the link that says “Your Benefit Verification Letter.” There you should see your dates. They are typically (but not always) the first of the month you turn 65.

☐ Enroll in Medigap, Part D or Medicare Advantage

You want to enroll in supplemental insurance so everything begins at the same time your Medicare starts. This is typically the first of the month you turn 65 years old.

• Medigap: This is our specialty. Get a Medigap quote and enroll here or schedule an enrollment phone call here.
• Part D covers prescription drugs: Senior65 usually doesn’t enroll members in Part D. To compare and enroll in a Part D plan, visit Medicare.gov/plan-compare
• Medicare Advantage: Senior65 typically doesn’t enroll clients in MA. To compare and enroll in a Medicare Advantage plan, visit Medicare.gov/plan-compare

Your 65th Birthday:

☐ Go Enjoy Your Life!

You should be set up with everything begining the first of the month you turned 65. Need help, give us a call.

You can learn more about how Medigap works or get a quote to see what plans are available in your area.

*What If You’re Still Working at 65?

If you’re covered under an active employer group health plan — through your own current job or your spouse’s — you may be able to delay Part B without penalty. Medicare gives you a Special Enrollment Period (SEP): you can enroll in Part B any time while that group coverage is active, or during the 8-month window that begins the month after employment ends or group coverage ends, whichever comes first.

Two things that do NOT count as current employer coverage: COBRA and retiree health coverage. If you’re on either of those at 65 and you don’t enroll in Part B, you’re not protected by the SEP — you’ll face a delayed enrollment and a late penalty.

💡 Tip: Even if you plan to delay Part B, contact Social Security at least 3 months before your 65th birthday to understand your specific situation. The rules interact differently depending on employer size and whether the group plan is primary or secondary to Medicare.

Getting Help With Your Medicare Decisions

Medicare enrollment isn’t complicated once you know the sequence — but the stakes are high enough that getting the order wrong can cost you. Our team has helped seniors navigate these decisions for more than 22 years. Comparing Medigap plans, understanding which carriers have stable rate histories, and applying before your guaranteed-issue window closes are all things we do every day.

Call 800-930-7956 to speak with a licensed agent on our team. Our help is free — we’re paid directly by the insurance carriers at no charge to you. No one can offer the same Medigap plan for less than Senior65.com!