Turning 65 in 2026? Your 6-Month Medicare Enrollment Checklist Starts Now!

Dec 15, 2025

The countdown to your 65th birthday has officially begun! If you’re based here in West Michigan and celebrating the big 6-5 sometime in 2026, you may think you have plenty of time. But when it comes to Medicare, timing is everything.

Your Initial Enrollment Period (IEP) is a seven-month window that revolves around your 65th birthday. Missing this window, or making the wrong decision during it, can lead to delayed coverage and potentially costly, lifelong penalties.

At Clear Benefit Solutions, we specialize in guiding West Michigan seniors through this crucial phase. We’ve put together a simplified 6-month checklist to help you start planning now, ensuring a stress-free transition to Medicare.

Step 1: The 6-Month Check-in (It’s NOT Too Early!)

Your Initial Enrollment Period (IEP) begins three months before the month you turn 65. The sooner you understand the rules, the safer you are from penalties.

  • Action Item: Contact Clear Benefit Solutions for a No-Cost Consultation. This is the most important step! We can instantly map out your exact 7-month window and determine what you need to do based on your personal situation (working or retiring).
  • The Big Question: Do I have to enroll in Medicare if I’m still working?
    • The Answer: It depends entirely on your employer’s size (20 or more employees vs. less than 20) and your current health plan. Making the wrong choice here can lead to late enrollment penalties for Part B that last for life. We’ll help you confirm your best strategy.

Step 2: 4 to 5 Months Out – The Parts of Medicare

You need to know the components you’ll be dealing with:

  • Part A (Hospital Insurance): Free for most people. If you or your spouse worked and paid Medicare taxes for at least 10 years, enroll ASAP!
  • Part B (Medical Insurance): This has a monthly premium. This is the part most people delay if they are still working and have credible employer coverage—but you must be certain your employer plan qualifies.
  • Part D (Prescription Drug Coverage): Crucial for preventing late enrollment penalties later on.
  • Part C (Medicare Advantage) or Medigap (Supplement): The two main ways to get the rest of your coverage.

 

Step 3: 3 Months Out – Time to Officially Enroll

This is when the clock is officially ticking. You need to start the formal enrollment process if you are retiring.

  • Action Item: Enroll in Part A and/or Part B through Social Security.
    • If you’re already receiving Social Security benefits, you’ll be automatically enrolled.
    • If you are not receiving Social Security, you must manually enroll online at SSA.gov.

Step 4: 2 Months Out – Designing Your West Michigan Plan

Once you’ve applied for Original Medicare (Parts A & B), you must decide how you want to manage your coverage gaps. The decision is usually between a Medicare Advantage (Part C) plan or a Medicare Supplement (Medigap) plan coupled with a Part D plan.

  • Action Item: Review Local Plans with a Local Agency. This is where our West Michigan expertise truly helps. We can compare plans based on:
    • Your preferred local hospitals and doctors (Spectrum/Corewell, Mercy Health, etc.).
    • Your specific prescription drugs (Part D plans vary wildly!).
    • Your budget for premiums vs. co-pays.

Step 5: Your 65th Birthday Month – Coverage Begins!

If you enrolled during the three months before your birthday month, your coverage starts on the first day of your birthday month. You’ll have your Medicare card and be ready to start your new plan.

🚨 Important Note on Medigap: Your 6-month Medigap Open Enrollment Period starts the month your Part B coverage begins. This is the only time you can purchase any Medigap policy regardless of your health status. If you miss it, you may be denied coverage later due to health conditions.

Don’t let deadlines and complex rules turn your 65th birthday into a headache. As your local, trusted Medicare experts in West Michigan, we provide the clarity you need to move forward confidently.

Contact Clear Benefit Solutions today to schedule your free 2026 Medicare Check-Up!