The 7 months around your 65th birthday is called the Initial Enrollment Period. It is the easiest, cheapest, penalty-free window you will ever have. Here is how to use it.
The 7-month window, in one picture
Your Initial Enrollment Period
3 months before your 65th birthday month · your birthday month · 3 months after. Start as early in this window as possible. Coverage starts faster, and you have time to compare plans without pressure.
What to do at each stage
Start learning. No decisions yet.
Read Medicare 101. Talk to friends who have already enrolled. If you are still working, ask HR about your retiree benefits and how they coordinate with Medicare. The earlier you understand the basics, the less rushed the actual decision feels.
Decide if you will keep working past 65.
If you have employer health coverage at a company with 20+ employees, you can usually delay Part B without penalty. If your employer is smaller, you typically need Medicare as primary. Get this answer in writing from HR. We will help you read it.
Enroll in Medicare Parts A and B.
Do this online at SSA.gov, or call Social Security. If you already collect Social Security, you are auto-enrolled. Otherwise, you must sign up yourself. Coverage will start the first day of your birthday month.
Choose your path: Medicare Advantage or Medigap + Part D.
This is the big decision. We compare every plan available in your ZIP code side by side, using your actual doctors and medications, so you can see costs and trade-offs clearly. The decision is yours, not ours.
Enroll in the plan you chose.
We handle the paperwork. You sign, we file. Your coverage starts the first day of your birthday month and your insurance card arrives in the mail within 2-3 weeks.
Coverage begins. Use it.
Schedule your Welcome to Medicare visit with your primary care doctor. It is free under Part B and a good chance to make sure your doctor is in-network and your prescriptions are covered.
Window closes. Late penalties begin.
If you missed the window and don't have qualifying employer coverage, you may face a permanent 10% Part B penalty per year of delay, plus a Part D penalty. There are workarounds in some cases. Call us before you panic.
The four most common mistakes we see
1. Auto-enrolling and accepting whatever Medicare assigns
If you already collect Social Security at 65, Medicare auto-enrolls you in Parts A and B. That part is fine. But Medicare does not pick a Medicare Advantage or Medigap plan for you, and Original Medicare alone leaves you exposed to unlimited out-of-pocket costs. You still need to choose a path.
2. Choosing a Medicare Advantage plan without checking the network
Networks change every year. Your favorite doctor or hospital may not be in next year's network even if they are this year. We check every doctor and every prescription against every plan before you decide.
3. Delaying Part B with the wrong kind of coverage
COBRA, retiree health, the marketplace — none of these qualify as "creditable coverage" that lets you delay Part B without penalty. Only active employer-group coverage at a 20+ employee company qualifies. Getting this wrong locks in a permanent late penalty.
4. Picking a Part D plan based on price alone
The cheapest Part D plan can be the most expensive if it does not cover one of your medications. We price your actual prescriptions on each plan's formulary, including tiers and pharmacy preferences, so the comparison is real.
If you are turning 65 in the next 3 to 6 months
Right now is the best time to get a free review. We will walk you through:
- Whether to enroll in Part B now or delay (and how to delay without a penalty)
- The Medicare Advantage vs. Medigap decision, side by side, with your real doctors and drugs
- Which Part D plan saves you the most based on your prescriptions
- How to coordinate Medicare with your spouse's coverage
- What to do if you are still working past 65
Let's make this simple.
Thirty minutes. On the phone, on video, or at our office in Fairview. No pitch, no paperwork, no obligation. Just a clear plan for the next 12 months.
Schedule a Free Review →