Medicare Checklist for Turning 65
Everything you need to do — and when to do it — to get Medicare right the first time. Month-by-month timeline from 3 months before your birthday through your first year on Medicare.
Missing a deadline can mean a permanent penalty and a gap in coverage. This checklist keeps you on track.
The 5 Decisions You Must Make When Turning 65
Enroll in Parts A & B
Apply at ssa.gov
Choose Your Coverage Path
Medigap or Advantage
Pick a Supplement or Advantage Plan
Compare carriers
Add Part D Drug Coverage
Match to your meds
Coordinate Existing Insurance
Cancel or transition
Still working at 65? If you have employer coverage through a company with 20+ employees, you may be able to delay Medicare without penalty. See our Medicare While Working guide before making any decisions.
Month-by-Month Medicare Checklist
3 Months Before Your 65th Birthday Month
Apply for Medicare Part A and Part B at ssa.gov/medicare
Select "Apply for Medicare Only" if you are not yet taking Social Security. Takes about 10 minutes online.
Confirm your Medicare card will arrive before your birthday
Your red, white, and blue Medicare card should arrive 2–3 weeks after applying.
Gather your current insurance information
You will need your current health insurance policy numbers, employer information, and coverage end dates.
Start researching Medicare Supplement vs Medicare Advantage
This is the biggest decision you will make. Talk to an independent broker who can compare both options.
Check if your doctors accept Medicare
Go to medicare.gov/care-compare to verify your physicians accept Medicare assignment.
2 Months Before Your 65th Birthday Month
Make your Medicare Supplement or Medicare Advantage decision
If choosing Medigap, apply now while you have guaranteed issue rights — no health questions required during your open enrollment window.
Apply for a Medicare Supplement (Medigap) plan if that is your choice
Apply 1–2 months before your Part B effective date. Coverage can start the same day as Part B.
Research Medicare Advantage plans in your ZIP code
Use medicare.gov/plan-compare to see all available plans, their networks, and star ratings.
Make a list of all your prescription medications
Include drug name, dosage, and frequency. You will need this to compare Part D plans.
Compare Part D prescription drug plans
Use medicare.gov/plan-compare with your medication list to find the plan with the lowest total annual cost.
1 Month Before Your 65th Birthday Month
Enroll in your chosen Medicare Advantage or Part D plan
Coverage starts on your Medicare effective date (usually the first of your birthday month).
Notify your current health insurance of your Medicare start date
Coordinate your coverage end date to avoid a gap or overlap.
Set up Medicare premium payment if not on Social Security
Enroll in Medicare Easy Pay at medicare.gov for automatic bank draft of your Part B premium.
Confirm your Medicare number and coverage details
Log in to mymedicare.gov to verify your enrollment is complete and your plan is active.
Check if you qualify for Extra Help with drug costs
If your income is limited, apply for Extra Help at ssa.gov to reduce Part D costs.
Your 65th Birthday Month — Coverage Begins
Confirm Medicare coverage is active
Log in to mymedicare.gov or call 1-800-MEDICARE (1-800-633-4227) to confirm your coverage start date.
Carry your Medicare card and supplemental plan ID card
You will need both at every medical appointment. Keep originals safe — carry copies if preferred.
Notify all your doctors of your new Medicare coverage
Provide your Medicare number and supplemental plan information to every provider.
Schedule your Welcome to Medicare preventive visit
Medicare covers a one-time Welcome to Medicare visit within the first 12 months of Part B enrollment. It is free — no copay.
Cancel or coordinate your previous health insurance
If you had COBRA or individual marketplace coverage, cancel it effective your Medicare start date to avoid paying double premiums.
After Enrollment — Ongoing Medicare Management
Review your Medicare plan every October 15–December 7
Annual Enrollment Period — compare plans each year. Drug formularies, premiums, and networks change annually.
Get your free annual wellness visit each year
Medicare covers an Annual Wellness Visit (AWV) at no cost. This is different from a regular physical — it is a preventive planning visit.
Take advantage of free preventive screenings
Medicare covers mammograms, colonoscopies, bone density tests, flu shots, and many other preventive services at no cost.
Monitor your Medicare Summary Notice (MSN)
Review your quarterly MSN for billing errors or services you did not receive. Report discrepancies to 1-800-MEDICARE.
Keep your income in mind for IRMAA planning
If your income is above $106,000 (individual) or $212,000 (married), you pay higher Medicare premiums. Plan accordingly.
The 5 Most Common Medicare Mistakes at 65
Missing the enrollment window
Apply 3 months before your birthday month. The 7-month window seems long, but processing takes time and late enrollment means a permanent penalty.
Assuming you are automatically enrolled
You are only auto-enrolled if you are already receiving Social Security. If you are delaying Social Security, you must actively apply for Medicare.
Choosing a plan without checking your doctors and drugs
Always verify your doctors are in-network (for Advantage) and your medications are on the formulary before enrolling in any plan.
Skipping Medigap because the premium seems high
The time to get Medigap is when you are healthy and have guaranteed issue rights. Once you develop health conditions, you may be denied Medigap forever.
Not reviewing your plan annually
Plans change every year. A plan that was perfect at 65 may have dropped your drug, raised your premium, or changed its network by 66. Review every October.
Frequently Asked Questions
Q.When should I apply for Medicare when turning 65?
Apply 3 months before your 65th birthday month for coverage to start on your birthday. This is the beginning of your 7-month Initial Enrollment Period.
Q.What do I need to do when I turn 65 for Medicare?
Apply for Parts A and B, decide between Medigap and Medicare Advantage, choose a plan, enroll in Part D drug coverage, and coordinate or cancel your existing health insurance.
Q.Do I need Medicare at 65 if I have employer insurance?
If your employer has 20+ employees, you can delay Medicare without penalty. If your employer has fewer than 20 employees, Medicare becomes primary and you should enroll at 65.
Q.What is the Medicare enrollment deadline at 65?
Your Initial Enrollment Period is 7 months: 3 months before your birthday month, your birthday month, and 3 months after. Missing it without a qualifying Special Enrollment Period results in a permanent penalty.
Q.Is Medicare free at 65?
Part A is usually free (premium-free if you worked 40+ quarters). Part B has a standard premium of $202.90/month in 2026. Part D and Medigap/Advantage plans have additional premiums.
Q.What happens if I miss my Medicare enrollment deadline?
You face a permanent 10% Part B penalty for each 12-month period you were eligible but did not enroll. You must wait for the General Enrollment Period (January 1–March 31) and coverage does not start until July 1.
Turning 65 Soon? Let's Walk Through It Together.
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Independent broker serving NE Florida — Palm Coast, Daytona Beach, Jacksonville, St. Augustine and surrounding areas.
Related Medicare Guides
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY: 1-877-486-2048) to get information on all of your options.
Not affiliated with or endorsed by the U.S. government or the federal Medicare program. This is an advertisement for insurance. William Gray and affiliated licensed agents are independent insurance agents, not government employees or representatives. Medicare has neither reviewed nor endorsed this information.
Not all plans or types of coverage may be available in your area. Plan availability, benefits, and premiums vary by county and ZIP code. Enrollment in any plan depends on contract renewal. Benefits, premiums, and cost-sharing may change on January 1 of each year.
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