I'm retiring. When do I sign up for Medicare, and what do I need to do?

Start with the coverage you have now

Retirement alone does not start Medicare coverage. Most people first get Medicare at 65; some can get it earlier. Confirm your eligibility with Medicare's getting-started guidance before ending existing insurance.

Check which Medicare parts you already have and when they start. Check where your health insurance comes from. It might be your current job, a former employer, a spouse's job, or another source.

Ask the benefits administrator for the exact day your job-based medical and drug coverage will end. Your last day at work and your last insured day may not be the same. Check what will happen to each family member on your plan, too.

Employer size and the kind of insurance can affect how coverage works with Medicare. Do not assume that having an insurance card means you can safely delay Parts A and B. Read Medicare.gov: working past 65 with your benefits administrator.

Separate Part B sign-up from choosing a plan

Signing up for Parts A and B is not the same as joining a Medicare Advantage or Part D drug plan. Fall Open Enrollment is not a substitute for checking your Part B sign-up window.

A Special Enrollment Period based on coverage from current employment may let you add Part B. You can add it while you are still working and covered. Or you can add it in the 8 months after the employment or job-based coverage ends, whichever ends first. Social Security must confirm which window applies to you.

Set up the start date before your old coverage ends. The sign-up window is not a promise of uninterrupted coverage. Ask Social Security when your Part B will really begin. Check Social Security's enrollment guidance.

Do not let leftover job insurance or retiree insurance hide a deadline

Continued job insurance (COBRA) can let you keep your job-based insurance for a while. But it does not extend the Part B enrollment period tied to current employment. Before you choose COBRA, check when Medicare needs to start and which insurer will pay your bills.

Retiree insurance may require both Parts A and B to pay full benefits. Joining a separate Medicare plan could also change benefits for you, a spouse or dependents. Before you cancel or change anything, ask your benefits office to explain. Read Medicare's COBRA guidance and retiree insurance guidance.

Give drug coverage its own deadline

Ask if your current drug coverage is creditable. That means it is expected to pay, on average, at least as much as Medicare drug coverage. Keep the written notices that say so, including the date that coverage ends.

Medicare lists a separate chance to join a Medicare Advantage or drug plan after you leave employer or union coverage, including COBRA. It lasts 2 full months after the month that coverage ends. Check which window applies and when the new plan starts. Also, do not assume the 8-month Part B window applies to drug coverage.

Once your first Medicare sign-up period is over, watch for gaps in drug coverage. A gap of 63 days or more may lead to a Part D late-enrollment penalty. A gap means no Medicare drug coverage and no other creditable drug coverage. The plan-joining window and the penalty rule are different checks, not a reason to wait.

Verify both with Medicare's plan Special Enrollment Periods and creditable drug coverage guidance. Ask about family benefits before adding separate drug coverage.

Check HSA contributions before Medicare starts

If you have an HSA, ask payroll and a qualified tax professional when to stop putting money in. That goes for you and your employer. The tax agency (IRS) sets your HSA limit to zero beginning with the first month you have Medicare. It counts every Medicare month, including retroactive coverage months.

Premium-free Part A can start up to 6 months before the month you apply if you apply after 65, subject to when you became eligible. Check the real start date with Social Security. Also, do not assume everyone gets a full 6 months of backdated coverage. That backdating can overlap HSA payments made before you applied. Do not use your retirement date alone to pick an HSA stop date. And do not assume Part A has no effect because you pay no premium for it.

Check Medicare's coverage-start guidance, Social Security's Part A timing guidance and IRS Publication 969. This guide does not calculate contribution limits or correct excess contributions.

If you are considering Medigap, check that window too

Medigap helps pay some costs in Original Medicare. It does not work with Medicare Advantage. The federal six-month Medigap Open Enrollment Period starts the first month you have Part B and are 65 or older. If Part B began earlier, that clock may already have started before you retire.

It does not restart each fall. Before you change coverage, ask about your buying rights. Free Medicare counseling can help. So can your state insurance department. Read the official Medigap basics, then review Medigap vs. Medicare Advantage if you need help understanding the two paths.

Apply through official channels and confirm the start dates

For Parts A and B, apply the official way through Social Security, or the Railroad Retirement Board if that applies to you. Say you already have Part A and are adding Part B after job-based coverage. Medicare says to have your employer fill out the Request for Employment Information form (CMS-L564). Check the steps and proof you need for your own case.

Use Medicare.gov's official sign-up instructions. Keep your submission confirmation, then confirm the actual start dates for Parts A and B and any separate plan. An application or comparison result is not proof that coverage is active.

Keep Medicare numbers, Social Security numbers and employment records off this page and out of chat. Send your sign-up papers to the agency, not to us. PlanScout does not enroll you in Medicare.

Questions to take to your benefits office or a free Medicare counselor

What are the last covered days for medical care and drugs? Which insurer pays first now, and after you retire? Do I need Parts A and B for this employer or retiree plan to pay its full benefits?

Is the drug coverage creditable, and can I have the notice in writing? What changes for my spouse or dependents if I join a separate Medicare plan? Which HSA months need checking? Who can confirm each sign-up deadline and coverage start date?

Bring the benefits booklet and coverage notices to your private planning conversation. You do not need to upload them here. Find free Medicare counseling in your state, or return to your Medicare planning starting points.

Checklist

• Confirm which Medicare parts are already active and their start dates.
• Write down the job end date and the separate medical and drug coverage end dates.
• Ask the benefits office how Medicare affects the employer or retiree plan and each family member's benefits.
• Confirm the Part B enrollment period and requested start date with Social Security.
• Keep the drug plan's creditable-coverage notice; confirm the separate plan-joining deadline and start date.
• Confirm HSA contribution timing with payroll and a qualified tax professional.
• If considering Medigap, check buying rights and timing before changing insurance.
• Use official enrollment channels, keep confirmations and verify active coverage before ending existing insurance.

Common questions