When you turn 65, you become eligible for Medicare and should start preparing three to six months before your birthday month. The most important steps are confirming your eligibility, deciding between Original Medicare and Medicare Advantage, comparing Part D prescription drug plans, and enrolling during your seven-month Initial Enrollment Period (the three months before your birthday month, your birthday month, and the three months after). Missing this window can trigger permanent late enrollment penalties on Parts B and D.

---

The Full Checklist

Turning 65 isn’t just another birthday — it’s the start of a coverage decision that follows you for life. Here’s exactly what to do, and when.

6 Months Before Your 65th Birthday

• Decide whether you’re keeping employer coverage. If you (or a spouse) are still actively working at a company with 20+ employees, you may be able to delay Part B without penalty. Confirm this with your HR department in writing.
• Check your Social Security status. If you’re already receiving Social Security benefits, you’ll be enrolled in Parts A and B automatically. If not, you’ll need to enroll yourself.
• Make a list of your doctors and prescriptions. This is the foundation of every plan comparison you’ll do. You’ll need names, dosages, and pharmacies.

3 Months Before Your 65th Birthday

• Apply for Medicare. Your Initial Enrollment Period opens. Enroll at SSA.gov, by phone, or at your local Social Security office.
• Decide your path: Original Medicare (Parts A + B) plus a Medicare Supplement and standalone Part D plan, or a Medicare Advantage plan (Part C) that bundles everything.
• Compare Part D drug plans. If you’re going the Original Medicare route, you’ll need a standalone Part D plan. Run your prescriptions through Medicare.gov’s plan finder to see total annual cost — not just premium.
• Talk to a licensed independent agent. A good advisor compares plans across multiple carriers. Captive agents only sell one company’s plans.

Your Birthday Month

• Confirm your Medicare cards arrived. Red, white, and blue. Keep one filed and one in your wallet.
• Activate your supplemental coverage. Whether that’s a Medigap policy, a Medicare Advantage plan, or a standalone Part D plan, make sure your effective date matches your Medicare start date.
• Notify your current insurer if you’re dropping employer or marketplace coverage.

After Enrollment

• Schedule a “Welcome to Medicare” preventive visit within the first 12 months — it’s free under Part B.
• Set a calendar reminder for October 15. That’s when the Annual Enrollment Period opens each year. Your plan can change, and so can your prescriptions — review annually.

---

The 4 Most Common Mistakes at 65

1. Assuming you’ll be auto-enrolled. You’re only auto-enrolled if you’re already receiving Social Security. Otherwise, you have to apply yourself.
2. Delaying Part B without qualifying coverage. Retiree coverage, COBRA, and marketplace plans do not count as creditable coverage for Part B. Delaying without true active employer coverage triggers a permanent 10% penalty for every 12 months you wait.
3. Picking a plan based only on premium. A $0-premium Medicare Advantage plan can cost more out-of-pocket than a $150/month Medigap plan, depending on how often you see specialists.
4. Using a captive agent. They can only sell one carrier’s plans, which limits your options. Independent agents compare across multiple companies.

---

Frequently Asked Questions

Will I be automatically enrolled in Medicare at 65?

Only if you’re already receiving Social Security or Railroad Retirement benefits before turning 65. In that case, you’ll receive your Medicare card in the mail about three months before your birthday, and Parts A and B start automatically on the first day of your birthday month. If you’re not yet collecting Social Security, you have to apply for Medicare yourself through SSA.gov or your local Social Security office.

What if I’m still working at 65?

If you work for a company with 20 or more employees and have group health coverage through your job, you can typically delay Part B without penalty. You’ll usually still want to enroll in Part A since it’s premium-free for most people. Once you retire or lose employer coverage, you’ll have an eight-month Special Enrollment Period to sign up for Part B without a penalty. Confirm in writing with your HR department that your coverage is creditable before delaying.

Do I need Medicare if I have other health insurance?

Most people should enroll in at least Part A at 65, since it’s premium-free if you’ve worked 10+ years. Whether to enroll in Part B depends on your other coverage. Active employer coverage at a large company usually lets you delay safely. Retiree coverage, COBRA, marketplace plans, and VA benefits typically do not — meaning you should enroll in Part B on time to avoid penalties. When in doubt, talk to a licensed Medicare advisor before declining Part B.

How much does Medicare cost at 65?

Most people pay nothing for Part A. The standard Part B premium is set annually by CMS and is tied to your income — higher earners pay more through IRMAA. Beyond that, your costs depend on the path you choose: Original Medicare plus a Medigap plan and Part D typically runs $150–$300/month total, while many Medicare Advantage plans have $0 premiums but higher out-of-pocket costs when you actually use care. The cheapest plan on paper isn’t always the cheapest plan in practice.

---

Ready to map out your Medicare options? Schedule a no-cost consultation with The Advocate Group → We’ll review your doctors, prescriptions, and budget — and compare plans from top carriers so you don’t have to.