Medicare Annual Enrollment: Oct 15 – Dec 7
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Turning 65 · New to Medicare

Turning 65? Here's your Medicare game plan.

When to sign up, what to sign up for, and how to avoid late penalties, in plain English. Our licensed agents walk you through it step by step.

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Your countdown

The months around your 65th birthday

Your Initial Enrollment Period is 7 months long: the 3 months before your birthday month, the month itself, and the 3 months after.

  1. 6 months before

    Get organized

    List your doctors and prescriptions. Ask your employer or union how your coverage works with Medicare. Book a call with us to map out your options.

  2. 3 months before

    Your window opens

    Your 7-month Initial Enrollment Period starts. If you're not already getting Social Security, you can sign up for Parts A and B at SSA.gov or your local office.

  3. Birthday month

    Coverage can start

    If you signed up early, Medicare usually starts the first day of your birthday month. Choose and enroll in your Supplement + Part D, or a Medicare Advantage plan.

  4. 3 months after

    Window closes

    Your Initial Enrollment Period ends. Signing up late without other qualifying coverage can mean late penalties and a gap in coverage.

  5. First 6 months of Part B

    Medigap open enrollment

    Your best time to buy a Medicare Supplement, when companies generally can't turn you down or charge more for health reasons.

Still working?

Working past 65 changes the plan

Many people delay Part B without penalty if they have qualifying coverage through their own or a spouse's current job. The rules depend on your employer, so check before you decide.

Often the case with larger employers

Your job plan may stay primary

If your employer's plan counts as coverage based on current employment, you may be able to delay Part B (and Part D if your drug coverage is creditable) and sign up later during a Special Enrollment Period.

Rules depend on employer size and plan type.

Often the case with smaller employers

Medicare may need to come first

With some smaller employers, Medicare pays first and your job plan pays second. Then you may need Parts A and B at 65 to avoid gaps. Ask your benefits office how their plan works with Medicare.

Retiree coverage and COBRA usually don't count as current-employment coverage for delaying Part B. Talk to us before you rely on them.
Free download

The Turning 65 Medicare checklist

A one-page checklist you can print and stick on the fridge.

  • ☐ Know your Initial Enrollment Period dates
  • ☐ Ask HR how your coverage works with Medicare
  • ☐ Decide whether to take Part A and Part B now
  • ☐ List your doctors and prescriptions
  • ☐ Compare Supplement + Part D vs. Medicare Advantage
  • ☐ Enroll and keep your confirmation letters

Send me the checklist

We'll email the checklist, and a licensed agent may follow up if you checked the box below.

We never sell your information.

FAQ

Turning 65 questions

Will I be enrolled in Medicare automatically?

If you're already getting Social Security benefits when you turn 65, you're usually enrolled in Parts A and B automatically and your card arrives in the mail. Otherwise, you sign up through Social Security.

Is Part A free?

Most people don't pay a premium for Part A because they or a spouse paid Medicare taxes long enough while working. Part B has a monthly premium.

What happens if I miss my enrollment window?

You may have to wait for the General Enrollment Period and could pay late enrollment penalties for Part B and Part D, unless you had qualifying coverage.

Do I need to do anything if I have an HSA?

Yes. Once you enroll in any part of Medicare you can't keep contributing to an HSA. Talk to your benefits office and tax advisor about timing.

When should I call you?

About 3 to 6 months before your 65th birthday is ideal, but we can help at any point.

Free, no-pressure help

Turning 65 soon? Let's map out your plan.

A free 15-minute call. We'll walk through your dates and choices, no pressure.