Turning 65 triggers the most important insurance decisions of your life, and the stakes are permanent. Missing your Medicare enrollment deadline results in a 10% Part B penalty per year of delay that you'll pay for life. Failing to apply for a Medicare Supplement during your 6-month Medigap Open Enrollment means you may never get guaranteed-issue rights again. According to CMS, approximately 750,000 beneficiaries are currently paying late enrollment penalties.
This checklist walks you through every step, month by month, so nothing falls through the cracks.
6 Months Before Turning 65: What Should You Start Planning?
- ✅ Verify your Social Security status. If you're already receiving Social Security benefits, you'll be automatically enrolled in Medicare Parts A and B. Your Medicare card will arrive about 3 months before your birthday. If you're not receiving Social Security, you must actively enroll.
- ✅ Determine whether to delay Part B. If you (or your spouse) have employer coverage through a company with 20+ employees, you may be able to delay Part B without penalty. Read our working past 65 guide for the rules.
- ✅ Start learning the basics. Understand the difference between Original Medicare (Parts A & B), Medicare Advantage (Part C), and Medicare Supplement (Medigap). These are fundamentally different coverage approaches.
- ✅ Make a list of all your doctors, specialists, and hospitals. You'll need this to verify network coverage for any plan you're considering.
- ✅ Make a list of all your medications. Include drug name, dosage, frequency, and quantity. This is critical for comparing Part D prescription drug plans.
3 Months Before Turning 65: What Steps Should You Take?
Your Initial Enrollment Period (IEP) begins 3 months before your birthday month. This is when the clock starts.
- ✅ Sign up for Medicare Parts A and B. Apply online at SSA.gov, by phone at 1-800-772-1213, or at your local Social Security office. Signing up in this 3-month window ensures coverage starts the 1st of your birthday month.
- ✅ Decide: Medicare Supplement or Medicare Advantage? This is the biggest decision. Read our complete Supplement vs. Advantage comparison. Key factors: Do you want to see any doctor (Supplement) or stay in a network (Advantage)? Do you prefer predictable costs (Supplement) or lower premiums (Advantage)?
- ✅ If choosing a Medicare Supplement: Start comparing carriers and rates. Remember, Plan G from one company covers the same things as Plan G from any other, only the premium and company differ. Focus on Plan G, Plan N, and High-Deductible Plan G.
- ✅ If choosing Medicare Advantage: Compare plans using the Medicare Plan Finder. Verify your doctors are in-network and your medications are on the formulary. Understand prior authorization requirements.
- ✅ Contact a licensed independent agent. An independent agent (not captive to one carrier) can compare all available options at no cost to you. The insurance company pays the agent, not you.
During Your Birthday Month: What Must You Do?
- ✅ Confirm your Medicare enrollment was processed. Check at Medicare.gov or call 1-800-MEDICARE. Verify your Part A and Part B effective dates.
- ✅ Apply for your Medicare Supplement plan. Your 6-month Medigap Open Enrollment Period starts this month. During this window, you have guaranteed-issue rights, no health questions, no denials, no waiting periods. This is the single most important enrollment window.
- ✅ Enroll in a Part D plan (if on Original Medicare + Supplement). Medicare Supplement plans don't include drug coverage. You must enroll in a standalone Part D plan separately. The new $2,100 annual cap makes this more affordable than ever.
- ✅ OR enroll in a Medicare Advantage plan. If you chose this path, enroll during your IEP. Most Advantage plans include Part D drug coverage.
- ✅ If you have employer coverage and are delaying Part B: Get written confirmation from your employer that your coverage is "creditable" (as good as Medicare). Keep this documentation, you'll need it when you eventually enroll in Medicare.
1 to 3 Months After Turning 65: What Should You Follow Up On?
- ✅ Verify all cards received. You should have: your red-white-and-blue Medicare card, your Supplement or Advantage plan card, and your Part D card (if separate).
- ✅ Set up your Medicare.gov account. Track claims, view your plan details, and access your Medicare Summary Notices (MSNs) online.
- ✅ Notify your prior insurance. If transitioning from employer or marketplace coverage, inform your prior insurer. Request a letter confirming your end date, this documents creditable coverage.
- ✅ Schedule your "Welcome to Medicare" preventive visit. This is a one-time preventive exam covered at no cost within the first 12 months of Part B. It includes health screenings, vaccinations review, and a prevention plan.
- ✅ Update your providers. Give your new Medicare and supplemental plan information to all your doctors, specialists, pharmacies, and hospitals.
First Year on Medicare: What Ongoing Steps Should You Take?
- ✅ Review your Explanation of Benefits (EOBs). Medicare sends these after each claim. Check that services were billed correctly and your supplement or advantage plan paid as expected. Read our guide to understanding EOBs.
- ✅ Know your Annual Enrollment Period (AEP). October 15, December 7 is when you can switch Medicare Advantage plans or change your Part D plan. Changes take effect January 1. Mark your calendar.
- ✅ Watch for your Annual Notice of Change (ANOC). If you're on Advantage or Part D, your plan sends this in September showing next year's changes to costs, coverage, and networks.
- ✅ Keep your Medigap OEP in mind. Your 6-month guaranteed-issue window is still open for the first 6 months after enrolling in Part B. If you started with Advantage and want to switch to a Supplement, you still have time within this window.
What If You're Still Working at 65?
About 20% of Americans 65 and older are still in the workforce. The rules depend on your employer's size:
| Employer Size | What to Do at 65 | Penalty Risk |
|---|---|---|
| 20+ employees | Enroll in Part A (free). Delay Part B until you retire or lose employer coverage. | No penalty, employer coverage counts as creditable |
| Under 20 employees | Enroll in Parts A AND B at 65. Medicare becomes your primary insurance. | 10% Part B penalty per year if you delay |
| Self-employed | Enroll in Parts A and B at 65. Your marketplace plan ends. | 10% penalty per year if you delay |
Read our complete guide to working past 65 with Medicare for detailed rules on HSAs, COBRA, and employer coordination.
Frequently Asked Questions About Turning 65
When should I start the Medicare process before turning 65?
Start 6 months early for research and planning. Begin your actual enrollment 3 months before your birthday month to ensure coverage starts on time. Don't wait until your birthday, you'll have a gap in coverage.
What's the biggest mistake people make when turning 65?
Missing the Medigap Open Enrollment Period. This 6-month window is your only guaranteed chance to buy a Medicare Supplement without health questions. If you start on Medicare Advantage and later decide you want a Supplement, you may not qualify. Learn about this and other common Medicare mistakes.
Do I have to take Medicare at 65?
Not necessarily. If you have creditable employer coverage through a company with 20+ employees, you can delay Part B. However, Part A is usually free and doesn't hurt to take at 65 (unless you have an HSA). When your employer coverage ends, you'll get a Special Enrollment Period to add Part B without penalty.
How much will Medicare cost me at 65?
Budget for $3,000 to $8,000 per year depending on your plan choice. With Original Medicare + Supplement Plan G + Part D, expect about $4,800/year total. With Medicare Advantage, expect about $2,500 to $3,000 in a healthy year (but potentially $9,000+ in a year with major health events). See our complete Medicare cost breakdown for Nebraska.
Can I get help choosing my Medicare plans?
Yes, and it's free. Independent insurance agents are paid by the insurance companies, not by you. An independent agent (unlike a captive agent who works for one carrier) can compare all plans available in your area. Schedule a free consultation or request a personalized quote.
If you're turning 65 in the Omaha area, check out our Turning 65 in Omaha guide for local plan options and costs.