Turning 65: Your Complete Medicare Enrollment Checklist

Turning 65 is a milestone—and one that comes with a to-do list. Medicare enrollment has specific deadlines and decisions that can affect your coverage and costs for years to come. This checklist helps you navigate the process step by step.

6-12 Months Before Turning 65

Start Learning

Medicare has a learning curve. Give yourself time to understand the basics before making decisions:

• Original Medicare (Parts A & B): The foundation—hospital and medical coverage from the government
• Medicare Advantage (Part C): An alternative way to get Medicare through private insurers
• Medicare Part D: Prescription drug coverage (standalone or included in Medicare Advantage)
• Medicare Supplement (Medigap): Supplemental coverage that works with Original Medicare

Assess Your Current Coverage

Understand what you have now:

• If you have employer coverage, check if it's "creditable" (as good as Medicare). If so, you may be able to delay enrollment
• If you have retiree benefits, understand how they'll coordinate with Medicare
• If you have COBRA, know that it's not creditable—you should enroll in Medicare
• If you have Marketplace coverage, you'll need to transition to Medicare

3 Months Before Your 65th Birthday

Your Initial Enrollment Period (IEP) Begins

Your IEP is a 7-month window:

• Starts 3 months before your birthday month
• Includes your birthday month
• Ends 3 months after your birthday month

When you enroll affects when coverage starts. Enrolling in the 3 months before your birthday starts coverage on the 1st of your birthday month—the earliest possible start.

Social Security Enrollment

If you're already receiving Social Security benefits, you'll be automatically enrolled in Parts A and B. Your Medicare card will arrive about 3 months before you turn 65.

If you're not yet receiving Social Security, you need to actively enroll. You can:

• Enroll online at ssa.gov
• Call Social Security at 1-800-772-1213
• Visit your local Social Security office

Decide: Part B Now or Later?

Part A (hospital coverage) is usually premium-free, so there's rarely a reason to delay it. But Part B (medical coverage) costs $174.70/month in 2025.

Enroll in Part B now if:

• You don't have creditable employer coverage
• Your employer has fewer than 20 employees
• You're retiring or losing employer coverage
• You have COBRA or Marketplace coverage

You may delay Part B if:

• You have creditable employer coverage through a company with 20+ employees
• Your spouse has such coverage and you're covered under it

Warning: Delaying Part B without creditable coverage triggers a late enrollment penalty—10% higher premiums for each 12-month period you were eligible but didn't enroll. This penalty is permanent.

During Your Birthday Month

Medigap Open Enrollment

If you're enrolling in Part B, your 6-month Medigap Open Enrollment Period begins. This is critical because:

• During this period, insurers must accept you regardless of health conditions
• They cannot charge more based on your health
• After this period, you may be denied coverage or charged more

If there's any chance you want Medigap in the future, this is the time to get it. You can always switch to Medicare Advantage later, but going from Medicare Advantage to Medigap can be difficult or impossible.

Make Your Coverage Decision

You need to choose one of two paths:

Path 1: Original Medicare + Medigap + Part D

• Sign up for Parts A and B
• Choose a Medigap plan (Plan G is most popular for new enrollees)
• Choose a standalone Part D drug plan

Path 2: Medicare Advantage

• Sign up for Part A and Part B (required)
• Choose a Medicare Advantage plan (usually includes drug coverage)
• Do NOT need separate Medigap or Part D

Gather Your Information

Before comparing plans, collect:

• List of your current doctors (names, addresses, phone numbers)
• List of your medications (names, dosages, quantities)
• Your budget for monthly premiums
• Your preferred hospitals and pharmacies

1-3 Months After Your 65th Birthday

Finalize Enrollment

Your IEP continues for 3 months after your birthday month, but waiting has drawbacks:

• Coverage starts later (1–3 months after enrollment)
• Less time to make decisions
• Rushing leads to mistakes

Receive Your Cards

You should receive:

• Your red, white, and blue Medicare card
• Your Medigap insurance card (if applicable)
• Your Medicare Advantage card (if applicable)
• Your Part D card (if standalone)

Inform Your Doctors

Let your doctors know about your new coverage. Provide them with your new insurance information so they can bill correctly.

Set Up MyMedicare.gov Account

Create an account at Medicare.gov to:

• View your coverage information
• Look up what's covered
• Track claims and spending
• Find Medicare-approved providers

Common Mistakes to Avoid

1. Missing Deadlines

Late enrollment penalties are permanent. Don't assume you can "figure it out later."

2. Assuming Employer Coverage Continues

Some employer plans end at 65; others become secondary to Medicare. Know what your plan does.

3. Keeping Only Part A

Some people take Part A only, thinking Part B is optional. If you don't have creditable coverage, you'll face penalties later.

4. Missing Medigap Open Enrollment

This 6-month window doesn't come back. If you think you might ever want Medigap, consider enrolling now.

5. Choosing Based Only on Premium

The lowest premium plan isn't always the lowest cost. Consider copays, drug costs, and out-of-pocket maximums.

Need Help?

Medicare enrollment has high stakes—wrong decisions can cost thousands and last for years. We provide free, personalized guidance to help you:

• Understand your deadlines
• Compare all your options
• Verify your doctors are covered
• Calculate your prescription costs
• Make an informed decision

Schedule Your Free Medicare Review