Still Working at 65? When You Can Delay Medicare Part B

Still working at 65 with good coverage through the job? You can wait on Medicare without a penalty. But there is a catch that trips a lot of people up — and it is not one catch, it is two clocks running at different speeds.

The basic rule

If you are still on the job’s health plan, you do not have to sign up for Part B at 65. No penalty. You wait until you retire.

Part A is a different story. The hospital side is premium-free for most people who worked about 10 years, so a lot of folks take Part A at 65 anyway and just delay Part B. Part B is the one that costs $202.90 a month in 2026.

The 20-employee line

This only works if the company has 20 or more employees. Smaller than that, Medicare has to be your main coverage anyway — so waiting leaves you with a gap in coverage and a penalty.

Call HR and ask for the employee count. Do not guess on this one. It is a two-minute phone call that decides whether your plan works.

Clock one: eight months for Part B

When you retire, you get 8 months to sign up for Part B. That clock starts the day your job ends or your coverage ends, whichever comes first.

COBRA does not count

This is the part that catches people. COBRA does not count as employer coverage for Medicare purposes. Neither does retiree coverage.

People take COBRA for a year figuring they are fine, and that 8-month clock has been running the whole time. When it runs out you are waiting until January to enroll, and paying a late penalty for the rest of your life.

Clock two: about 63 days for Part D

Here is the second clock, and it is the one almost nobody mentions. That 8 months is only for Part B. Your drug coverage is Part D, and that one gives you about two months — call it 63 days.

Go past it and you pick up a whole separate penalty, also for life. And if you are on COBRA, ask them in writing whether the drug side counts as creditable coverage. Usually it does not.

Two things to do

If you are working past 65: ask HR the employee count, and the day you retire, start the Part B paperwork. Do not let COBRA fool you into thinking you have more time than you do.

Common questions

Do I have to take Medicare at 65 if I am still working?

Not Part B, as long as your employer has 20 or more employees and you are on their plan. Most people take premium-free Part A anyway.

Does COBRA count as creditable coverage for Medicare?

No. COBRA does not delay your Part B enrollment window, and its drug coverage often is not creditable for Part D either. Get that answer in writing.

What is the Part B late enrollment penalty?

It is added to your premium and it lasts for life. That is why the 8-month window matters so much.

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I am Rick Caso, an independent Medicare advisor with Falcon Life and Health, based in Port Charlotte, Florida and licensed in 24 states. If you want to walk through your own situation, call or text 941-412-2362.