Medicare After 65: The Complete First-Year Checklist

Checklist: 3–6 Months Before Turning 65

Review your current coverage. Do you have employer insurance? VA care? TRICARE? Marketplace coverage? Understanding what you have now determines what you need from Medicare.
Check if your coverage is creditable. Employer (20+ employees) = creditable. TRICARE = creditable. VA care = NOT creditable for Part B. Marketplace = NOT creditable. This determines whether you can delay Part B.
Sign up for Part A. Free for most people. Apply at ssa.gov or call 1-800-772-1213 up to 3 months before turning 65.
Decide on Part B. If you don't have creditable coverage, sign up now. The 7-month IEP window has already started. See our Part B Guide.
Research your options. Start comparing Original Medicare + Medigap + Part D vs. Medicare Advantage. See our MA vs. Medigap Guide.
Call SHIP. Free, unbiased counseling. 877-839-2675 or shiphelp.org.

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Checklist: The Month You Turn 65

Confirm your Medicare enrollment. Check that Part A (and Part B if applicable) is active. You should receive your Medicare card in the mail.
Choose your path: Enroll in a Medicare Advantage plan OR stay with Original Medicare and add a Medigap supplement + Part D drug plan.
Medigap Open Enrollment starts NOW. Your 6-month guaranteed-issue window begins the month Part B is effective. This is your one shot to buy any Medigap plan without health questions. Don't let it close without deciding. See our Enrollment Periods Guide.
Enroll in Part D. If you chose Original Medicare, you need a standalone Part D plan. If you chose Medicare Advantage, Part D is usually built in. See our Part D Guide.
End Marketplace coverage. If you have an ACA Marketplace plan, end it when Medicare starts. You lose subsidy eligibility once you're Medicare-eligible.

Dr. Ed's Insider Tip

The month you turn 65 is the busiest month of your Medicare life. You're making decisions that will affect your healthcare and finances for decades. Don't rush, but don't delay either. If you feel overwhelmed, call SHIP at 877-839-2675. That's literally what they're there for.

Need Help Making These Decisions?

Your first year on Medicare involves the biggest decisions you'll make about healthcare. Chapter's licensed advisors walk you through every step — plan comparison, enrollment, cost analysis — completely free.

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Checklist: First 3 Months on Medicare

Schedule your "Welcome to Medicare" visit. A free preventive visit covered by Part B in your first 12 months. No copay. Establishes a baseline for your health.
Set up your Medicare.gov account. Track claims, check coverage, compare plans, and manage your information online.
Check for Medicare Savings Programs. If your income is limited, MSPs can pay your Part B premium and more. See our MSP Guide. Apply through your state Medicaid office.
Check for Extra Help. If your income is under $2,015/month, you may qualify for Extra Help with Part D drug costs. See our Extra Help Guide. Apply at ssa.gov/medicare/part-d-extra-help.
Understand your costs. Part B premium: $202.90/month. Part B deductible: $283/year. Part A deductible: $1,736 per benefit period. Know what you owe before you get a surprise bill.
Carry your card. Show your Medicare card (and Medigap or MA card if applicable) at every healthcare visit.

Checklist: Before Your First Anniversary

Review your coverage during AEP (Oct 15 – Dec 7). Compare your current plan to alternatives. Drug formularies, networks, and premiums change every year.
Use the Medicare Plan Finder. Enter your drugs and pharmacy at medicare.gov/plan-compare to see which plan is cheapest for YOUR medications next year.
Check your IRMAA. If your income is above $109,000 (single) or $218,000 (joint), you may be paying a surcharge. See our IRMAA Strategies Guide.
Get your preventive services. Annual wellness visits, cancer screenings, flu shots, and other preventive care are covered at $0 under Part B. Use them.
Know your Medigap window status. If you're still in your 6-month Medigap OEP, make your final decision before it closes. After it closes, guaranteed-issue Medigap is generally not available.

Dr. Ed's Insider Tip

Your first year on Medicare sets the foundation for everything that follows. The decisions you make — or don't make — in these 12 months affect your costs and coverage for the rest of your life. Take it seriously, use the free resources available, and don't be afraid to ask for help.

Frequently Asked Questions

If you have creditable employer coverage (20+ employees), you can delay Part B without penalty. But sign up for Part A — it's free and doesn't conflict with employer coverage. When you stop working or lose coverage, you get 8 months to enroll in Part B.

You must take Part A if you're receiving Social Security. Part B is optional but recommended. If you have non-creditable coverage and don't enroll in Part B, you'll face a permanent penalty.

You should still enroll in Part D (or an MA plan that includes Part D). If you don't and later need medications, you'll pay a late enrollment penalty that increases every year you were without coverage.

With Original Medicare + Medigap, you can see any doctor who accepts Medicare (most do). With Medicare Advantage, you'll need to use the plan's network. Always check before enrolling.

Start Here

Should I Sign Up for Part B? →

How to Choose Part D →