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Medicare guide

Turning 65: Your Medicare Checklist, Month by Month

Start about 6 months before you turn 65. Decide whether you need Part B now or can delay because of job-based coverage, sign up during your 7-month Initial Enrollment Period, then choose how you’ll get coverage — Medigap plus Part D, or Medicare Advantage — before your Medicare start date.

By the Kryder Cares Data Desk · Reviewed by Kris Kryder, licensed agent · Updated

Key points

  • Your Initial Enrollment Period starts 3 months before your 65th-birthday month.
  • Sign up before your birthday month and coverage starts the month you turn 65.
  • Already on Social Security 4+ months before 65? You’re enrolled automatically.
  • Your 6-month Medigap Open Enrollment Period starts with Part B at 65 or older.

Six months before: gather the facts

Turning 65 brings a lot of mail, and much of it is advertising. Before any of it, answer three questions for yourself:

  • Will you still have job-based coverage from current work? If you or your spouse work for an employer with 20 or more employees, you may be able to delay Part B. Read working past 65.
  • Do you have a Health Savings Account? CMS says you and your employer should stop HSA contributions 6 months before you retire or apply for Social Security benefits, because Part A can start up to 6 months earlier than your application.
  • Which doctors, hospitals and prescriptions matter most? Write them down — you’ll need the list to compare plans.

Three months before: your Initial Enrollment Period opens

Your Initial Enrollment Period is 7 months: the 3 months before your birthday month, the month itself and the 3 months after. If your birthday falls on the first of the month, Medicare counts you as turning 65 the month before, so everything shifts a month earlier.

If you’re already receiving Social Security (or Railroad Retirement Board) benefits at least 4 months before 65, you don’t need to do anything — Parts A and B start automatically and the card arrives about 3 months ahead. Otherwise, Kris files your Part A and B application with Social Security with you.

Sign up in these 3 months and Part B starts the first day of your birthday month. Sign up in your birthday month or later and it starts the month after you sign up. See your own dates with our enrollment window finder.

Before your start date: choose how you’ll get coverage

Once you know your Part A and B start dates, decide how you’ll receive your benefits. There are two main routes:

  • Original Medicare + Medigap + Part D. Any provider in the U.S. that accepts Medicare; a Medigap policy for the gaps; a separate drug plan.
  • Medicare Advantage (Part C). One plan, usually with drug coverage, a network and a yearly limit on what you pay for covered services.

Your Medigap window and your drug coverage

If Medigap appeals to you, your Medigap Open Enrollment Period begins the first month you have Part B and are 65 or older and lasts 6 months. During it, companies can’t turn you down or charge you more for health reasons. It happens once, so it’s worth deciding inside that window. Our comparison guide lays out the trade-offs.

Don’t skip drug coverage. If you go 63 days or more without Part D or other creditable coverage after your Initial Enrollment Period, a lifelong penalty can apply. Our Part D guide covers 2026 and 2027 costs.

In your birthday month and after

  • Watch for your Medicare card and check the Part A and Part B start dates printed on it.
  • Confirm your new plan’s ID card arrives and your pharmacy has it on file.
  • If you joined a Medicare Advantage plan during your Initial Enrollment Period, you can switch plans or return to Original Medicare within your first 3 months of having Parts A and B.
  • Cancel any Marketplace plan so it ends when Medicare starts; once you’re eligible for Part A, you can’t keep getting Marketplace premium help.

Where to get help in northwest Ohio

Kris Kryder has helped people around Perrysburg, Toledo and the rest of northwest Ohio through this transition since 2017, in person at her office or by phone and video. She’ll map your dates, check your doctors and prescriptions against the plans she represents, and handle the applications. Her longer Ohio turning-65 article and the Medicare videos are good next reads, along with Medicare planning.

Your next step

Have questions about your own situation? Contact Kris or schedule a no-cost meeting. You can also read more about Medicare Advantage, Medicare Supplement (Medigap) and Medicare Part D.

Sources

  • CMS — When can I sign up for Medicare?
  • CMS — When does Medicare coverage start?
  • CMS — How do I sign up for Medicare?
  • CMS — Working past 65
  • CMS — Get ready to buy a Medigap policy
  • CMS — Joining a plan (enrollment periods)
  • CMS — Compare Original Medicare & Medicare Advantage

We do not offer every plan available in your area. Currently we represent 14 organizations which offer 119 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. This is a proprietary website and is not associated, endorsed or authorized by the Social Security Administration, the Department of Health and Human Services or the Center for Medicare and Medicaid Services. This site contains decision-support content and information about Medicare, services related to Medicare and services for people with Medicare. If you would like to find more information about the Medicare program please visit the Official U.S. Government Site for People with Medicare located at www.medicare.gov.

This guide is general education, not a recommendation for any specific plan or policy. Figures were current as of October 19, 2026; plan details and government amounts change every year.

FAQ

Questions people ask

How early can I sign up for Medicare before 65?

Three months before your 65th-birthday month, when your Initial Enrollment Period opens. Signing up then means Part B starts the first day of your birthday month. If your birthday is on the first of the month, everything starts one month earlier. Kris Kryder checks your dates and handles the enrollment with you at no cost. Call (419) 277-8097.

Do I have to sign up for Medicare if I’m still working?

Not always. If you or your spouse have group coverage from current work with an employer of 20 or more employees, you can usually delay Part B without a penalty. Many people still take Part A if it has no premium. Check with your benefits office first. Kris Kryder checks your dates and handles the enrollment with you at no cost. Call (419) 277-8097.

When should I stop contributing to my HSA?

CMS says you and your employer should stop HSA contributions 6 months before you retire or apply for Social Security benefits. Part A can start up to 6 months before your application month, and contributions while you have Part A can create a tax penalty. Kris Kryder checks your dates and handles the enrollment with you at no cost. Call (419) 277-8097.

Will I get my Medicare card automatically?

Yes, if you started Social Security or Railroad Retirement Board benefits at least 4 months before you turn 65. The card arrives about 3 months before coverage starts. If you haven’t started benefits, Kris files your application with Social Security with you.

When should I buy a Medigap policy?

Many people buy during their 6-month Medigap Open Enrollment Period, which starts the first month they have Part B and are 65 or older. During that window, companies can’t deny coverage or charge more because of health problems. Kris Kryder checks your dates and handles the enrollment with you at no cost. Call (419) 277-8097.

Can Kris help me with turning 65?

Yes. Kris works with people several months before 65 to map their enrollment dates, review job-based coverage and compare plans she represents. Meetings are no cost and no obligation, in Perrysburg or by phone and video. Call (419) 277-8097.

Talk with Kris today — no cost, no obligation, no pressure

Meet in person at the Perrysburg office, or by phone or video. Bring your questions; Kris brings the side-by-side comparisons.

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