Retiring Soon? Don’t Miss These Medicare Deadlines

Justin Hundley
May 2
2 min read

If you’re planning to retire soon — congrats! 🎉 But before you celebrate, don’t forget to plan for one of the most important pieces of your retirement: Your Medicare plan.

Missing key Medicare deadlines can lead to:

Costly penalties
Gaps in coverage
Delays in when your benefits begin

Let’s make sure you’re covered when the big day comes.

Woman sitting at a table with a birthday cake with the number 65 candles on it — Turning 65? We can help you sign up for Medicare!

📅 Medicare Enrollment Timeline for Retirees

For most people, Medicare enrollment starts with the Initial Enrollment Period (IEP) — a 7-month window:

✅ 3 months before, the month of, and 3 months after your 65th birthday.

Still working at 65? Special rules may apply.

💡 Pro Tip: Even if you have employer coverage, you may still need to enroll in Medicare Part A on time to avoid penalties.

⚠️ What Happens If You Miss Your Medicare Sign-Up Window?

Delaying your enrollment can result in:

❌ Late enrollment penalties (they stick with you for life!)
🕒 Delays in coverage when you need it most
💸 No prescription drug coverage if you skip Part D
💊 Higher out-of-pocket costs due to gaps in coverage

🧾 Retiring After Age 65?

If you’ve delayed retirement past 65 and had qualifying employer health coverage, you may qualify for a Special Enrollment Period (SEP).

You’ll have 8 months after your coverage ends to enroll in Medicare without penalty.

🚫 Note: COBRA does not count as employer coverage for Medicare. Delaying too long could cost you.

🔍 Choosing the Right Medicare Plan When You Retire

Once enrolled in Medicare, your next step is choosing between:

✅ Medicare Advantage (Part C)

Combines hospital, medical, and often drug coverage
May include extras like dental, vision, and fitness
Requires staying within a provider network

✅ Medicare Supplement (Medigap) + Part D

Helps pay out-of-pocket costs Medicare doesn’t cover
Use any doctor that accepts Medicare
Part D adds drug coverage separately

💬 Not sure which is right for you? We help you compare Medicare Advantage vs Medigap, and find a plan near you that fits your doctors and prescriptions.

⏳ Countdown to Medicare: Your Retirement Timeline

Stay on track with these simple steps:

Time Before Retirement	What to Do
✅ 6 Months Out	Start researching plans, list doctors & prescriptions
✅ 3 Months Out	Meet with a local Medicare agent to explore your options
✅ 1 Month Out	Finalize your Medicare enrollment & check provider networks