Turning 65 Medicare Checklist: Month-by-Month Guide

Turning 65 brings a set of Medicare decisions with real deadlines. Miss one and you could face a lifelong penalty or a gap in coverage. Get them right and the process is manageable. This checklist follows the timeline month by month, covers what to do if you are still working, and explains the one-time Medigap window that many people do not learn about until it has closed.

Key takeaways

• Your Initial Enrollment Period (IEP) is seven months: three months before your birthday month, the month itself, and three months after.
• If you are still working with coverage from a larger employer, you may be able to delay Part B without penalty. Smaller employers are different.
• Your Medigap open enrollment window is six months, starting when you are 65 and enrolled in Part B. It does not repeat.
• Part B and Part D both have late enrollment penalties. Part B's can last for life.
• Higher-income households may pay more for Parts B and D under IRMAA rules.

The Medicare basics you need first

Medicare has four parts:

• Part A covers hospital stays, skilled nursing facility care, hospice, and some home health care. Most people pay no premium for Part A.
• Part B covers doctor visits, outpatient care, preventive services, and medical equipment. Part B has a monthly premium.
• Part C (Medicare Advantage) is a private plan that bundles Parts A and B, usually with drug coverage, and must cover everything Original Medicare covers.
• Part D is prescription drug coverage from a private plan.

Medigap (Medicare Supplement) is a separate private policy that pays some of the costs Original Medicare leaves to you. You cannot have Medigap and Medicare Advantage at the same time. Our guide to Medicare Advantage vs. Medigap explains that choice in detail.

Your 7-month Initial Enrollment Period

The IEP is built around your 65th birthday month.

If your birthday is on the first of the month, your coverage and your IEP shift one month earlier. Confirm your dates on Medicare.gov or with Social Security.

Six months before: get organized

• Check whether you will be enrolled automatically. If you already receive Social Security or Railroad Retirement benefits, Medicare enrolls you in Parts A and B and mails a card about three months before your birthday month. If not, you will apply yourself.
• Find out how your current coverage works with Medicare. Ask your HR or benefits office for written confirmation of how many employees the company has and whether the plan is creditable for prescription drugs.
• If you have a Health Savings Account (HSA), know that you cannot contribute once you are enrolled in any part of Medicare. Part A enrollment can be backdated up to six months when you apply after 65, so people who plan to keep working and contributing should talk to a tax professional about timing.
• Make lists. Write down every doctor you see, every prescription you take, and roughly what you spend on health care today.

Three months before: decide and apply

This is the start of your IEP, and it is the ideal time to act.

1. Apply for Medicare at ssa.gov if you are not enrolled automatically. You can apply online.
2. Decide on Part B. If you are retiring or your employer coverage is ending, enroll now. See the working section below if you are not.
3. Choose your path: Original Medicare plus Medigap and Part D, or a Medicare Advantage plan.
4. Shop plans. Use Medicare.gov's Plan Finder, and consider talking to a licensed agent who can check your doctors and prescriptions against each plan. Our how to choose a Medicare agent guide explains what to look for.
5. Enroll in Part D or a Medicare Advantage plan with drug coverage. Your Part D IEP matches your Medicare IEP.

Your birthday month: confirm everything

• Confirm your Medicare card arrived and shows the start dates you expected.
• If you chose Medicare Advantage or Part D, confirm you received the plan's welcome packet and ID card.
• If you chose Medigap, this is the start of your six-month Medigap open enrollment period (assuming Part B starts this month).
• Tell your doctors' offices about your new coverage so their billing records are updated.

Three months after: last call for your IEP

If you have not enrolled, this is the end of your window. Signing up in these months means coverage starts the month after you apply, so you could have a gap. If you miss the IEP entirely and do not have a Special Enrollment Period, you generally wait for the General Enrollment Period at the start of the next year, and penalties may apply.

Still working at 65? Read this carefully

Whether to enroll in Part B while working depends mostly on the size of the employer and whether the coverage comes from active employment.

If you delay Part B because of active employer coverage, you get an eight-month Special Enrollment Period that starts when the employment or the coverage ends, whichever comes first. You will need proof of employer coverage when you enroll. Note that your Medigap open enrollment period also does not begin until you are enrolled in Part B.

Many people in this situation still enroll in Part A at 65 because it is premium-free for most people. The exception is anyone who wants to keep contributing to an HSA.

The Medigap window explained

Your Medigap open enrollment period lasts six months and begins the first month you are 65 or older and enrolled in Part B. During this window, insurers must sell you any Medigap plan they offer in your state, regardless of your health, at the best available rate for your age.

Once it ends, most states allow insurers to ask health questions, charge more, or decline you. A few states have extra protections, so check your state's rules. If you start with Medicare Advantage and want to switch to Medigap later, you may need to pass underwriting unless you qualify for a guaranteed issue right, such as the trial right during your first year of Medicare Advantage.

Penalties and income-based premiums

• Part B late enrollment penalty. If you go without Part B when you were eligible and had no qualifying employer coverage, your premium can be increased for as long as you have Part B. The penalty grows with each full year you waited.
• Part D late enrollment penalty. If you go without creditable drug coverage for a stretch of time after your IEP, you may pay a monthly penalty added to your Part D premium, generally for as long as you have Part D. Employer plans, VA coverage, and some other sources can count as creditable coverage. Get it in writing.
• IRMAA. If your income is above certain thresholds, you pay a higher Part B and Part D premium. Social Security uses your tax return from two years earlier. If your income dropped because of retirement or another life-changing event, you can ask Social Security to reconsider. Check the current year's thresholds on medicare.gov or ssa.gov.

Printable checklist

• Know your IEP dates
• Confirm whether you are auto-enrolled
• Get employer coverage details in writing
• Decide on Part B (enroll or delay with qualifying coverage)
• Stop HSA contributions before Medicare starts, if applicable
• List doctors and prescriptions
• Choose Original Medicare + Medigap + Part D, or Medicare Advantage
• Enroll in drug coverage to avoid the Part D penalty
• Note your six-month Medigap window
• Confirm cards and start dates

Talk to a licensed agent for free

Medicare agents are paid by the insurance carriers whose plans they sell, so their help costs you nothing extra, and your premium is the same whether you enroll on your own or with an agent. A licensed agent can map out your enrollment dates, compare Medigap and Medicare Advantage plans against your doctors and prescriptions, and make sure you do not miss a window. You can browse Medicare agents by state or find a licensed health insurance agent near you at no cost.