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1. You're Turning 65

You get a 7-month window around your birthday: the 3 months before your birthday month, your birthday month, and the 3 months after.

  • Sign up in the 3 months before your birthday month so your coverage starts on time, with no gap.
  • Already getting Social Security? You're enrolled automatically — your card arrives about 3 months before you turn 65.
  • Miss your window and you could pay a late penalty for life, so it's worth marking the date.

2. You're Losing Job-Based Coverage After 65

Still working at 65 (or covered by a spouse who is) with insurance from that job? You can usually delay Medicare without a penalty while that coverage lasts.

  • When the job-based coverage ends, you get an 8-month Special Enrollment Period to sign up for Part B — no penalty.
  • Important: COBRA and retiree coverage do not count as active job coverage. Don't wait on those — sign up when the employment coverage ends.
  • Not sure if your employer coverage lets you delay? That's a quick question worth asking before you decide.

3. You Have Medicaid or a Limited Income

If money is tight, you may qualify for programs that help pay your Medicare premiums and prescription costs — and sometimes more.

  • If you have both Medicare and Medicaid, there are plans built specifically for your situation, and you can usually make changes more often than other people.
  • Billions of dollars in this help goes unclaimed every year simply because people don't know it exists.
  • It's worth a short conversation to see what you qualify for — at no cost to you.

Not Sure Which One Is You?

These three cover most people, but life doesn't always fit in a box — maybe you're turning 65 and still working, or moving states at the same time. That's exactly what a quick, no-pressure conversation is for. We'll figure out your timing together so you don't miss a deadline or pay a penalty you didn't need to.

Let's Figure Out Your Timing

Tell us your situation and we'll walk you through exactly when and how to enroll — at no cost to you.

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