If you are 65 or older and still working in New York, you may be able to wait to sign up for Medicare Part B without a penalty, but only if you or your spouse have group health coverage from a current job, and the size of the employer matters. When that job or coverage ends, you get 8 months to sign up. The rules are federal, so they are the same in Manhattan, Brooklyn, Queens, the Bronx, Long Island, Westchester, Albany, Syracuse, Rochester or Buffalo.
This article is educational. Instant Health Help is a licensed health insurance agency, and our agent, Lobsang Rivas, is licensed in New York and certified as a broker with NY State of Health. We are not Medicare, Social Security, NY State of Health, your employer, or an insurance company. We do not quote prices or name plans here. See the official Medicare.gov page on working past 65.
The short answer
- Employer with 20 or more employees: your job plan usually pays first, and you may be able to delay Part B without a penalty.
- Employer with fewer than 20 employees: Medicare usually pays first, and your job plan might not pay your bills if you don’t have Parts A and B. Sign up when you are first eligible.
- COBRA and retiree coverage don’t count as coverage from current work.
- When the job or the coverage ends, you have 8 months to sign up for Part B without a penalty.
Why employer size matters
Medicare.gov’s who pays first rules say that if you are 65 or older and have group coverage based on your or your spouse’s current employment, the job plan pays first when the employer has 20 or more employees. If the employer has fewer than 20 employees, Medicare pays first. Ask your benefits office how your plan works with Medicare before you decide. This matters in New York, where many people work for unions, city and state agencies, hospitals, universities, banks, building trades and small businesses.
Part A while you work
If you don’t have to pay a premium for Part A, Medicare.gov says you can choose to sign up when you turn 65 or any time later. One caution: if you have a health savings account (HSA), Medicare.gov says you and your employer should stop contributing 6 months before you retire or apply for Social Security benefits, to avoid a tax penalty.
The 8-month window
Your 8-month special enrollment period starts when you stop working or lose the group coverage, whichever happens first, even if you choose COBRA. COBRA does not extend it. If you take COBRA and wait until it ends, you may miss the window and face a late penalty. Medicare.gov explains that the Part B penalty is 10% for each full 12-month period you could have had Part B but didn’t, and you usually pay it for as long as you have Part B. See how to avoid penalties.
To avoid a gap, Medicare.gov suggests checking when your job coverage ends and signing up about a month earlier. On the form, you can note the month you want Part B to start.
The forms
If you sign up for Part B after 65 because you had job coverage, Social Security asks for two forms:
- CMS-40B, the application for Part B.
- CMS-L564, the request for employment information. Your employer fills out Section B to show when you had group coverage.
If your employer can’t complete Section B, CMS lists other proof you can send, such as income tax returns that show health premiums paid, W-2s showing pre-tax medical contributions, pay stubs showing health premium deductions, health insurance cards with a policy date, explanations of benefits, or premium receipts. You can apply online with Social Security or call 1-800-772-1213 (TTY 1-800-325-0778). See signing up for Part B only and the CMS-L564 page.
Drug coverage and Medigap
If your job plan includes drug coverage, ask whether it is creditable, meaning it is expected to pay on average at least as much as Medicare’s standard drug coverage. If you go 63 days or more without creditable drug coverage after your initial enrollment period, a Part D late penalty may apply.
Your 6-month Medigap open enrollment period starts the first month you have Part B and are 65 or older, so delaying Part B also delays it. Read our guide to Medigap guaranteed issue in New York.
A younger spouse on your job plan
If your spouse is under 65 and loses your job coverage when you retire, that loss can open a special enrollment period through NY State of Health. Report it within 60 days. See NY State of Health special enrollment or call 1-855-355-5777 (TTY 1-800-662-1220). The Essential Plan, Medicaid and Child Health Plus take enrollments all year for people who qualify. Read our Essential Plan guide and our New York open enrollment guide.
Our agent is certified as a broker with NY State of Health, so for a spouse or adult child under 65, we can go through the application with you, compare plans, and help you enroll, at no extra cost to you for our help. We are not NY State of Health, and NY State of Health decides what you qualify for.
Help with costs and every fall
If your income is limited, see our guides to the Medicare Savings Program in New York and EPIC. Once you have Medicare, our New York Medicare annual enrollment guide explains what to review each fall.
Unbiased counseling: HIICAP
New York’s Health Insurance Information, Counseling and Assistance Program (HIICAP) offers Medicare counseling through local offices for the aging. Call the HIICAP helpline at 1-800-701-0501 or visit the HIICAP page.
How we help
We are licensed in New York and help by phone and online, in English or Spanish. Learn more on our New York health insurance help page. We can help you build a timeline around your retirement date, list the questions to ask your benefits office, walk through the CMS-40B and CMS-L564 with you, check your doctors and medicines, compare plans, and help you enroll if you decide to. The choice is always yours.
Want to talk it through?
Have your planned retirement date, your employer’s benefits information, your spouse’s age and your list of medicines, and we will go over your timing step by step.
Call (321) 315-0054 | agent@inshh.com
We do not offer every plan available in your area. Currently we represent 10 organizations which offer 489 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, is available 24 hours a day, 7 days a week, except some federal holidays. Instant Health Help is not connected with or endorsed by the U.S. government or the federal Medicare program.
Featured photo: Brooklyn Bridge and Lower Manhattan from Brooklyn Bridge Park by Jakub Hałun, CC BY 4.0, cropped with text added.