When do I sign up for Medicare if I’m still working

Enrollment
Last updated: 
April 10, 2026
Smiling elderly couple on medicare coverage sitting outdoors in a grassy hilly area, dressed warmly with scarves and jackets.
Smiling elderly man with pre existing conditions is grateful for medicare insurance and woman enjoying tea together indoors with plants in the background.
Older couple smiling wondering about their drug formulary and dancing outdoors among green trees, enjoying a healthy aging lifestyle.

The short answer

If your employer has 20 or more employees, you can usually wait until you stop working to sign up for Part B without a penalty. However,most people still sign up for "premium-free" Part A during their 65thbirthday window just to have that extra hospital coverage.

The full explanation

When you turn 65, you enter what’s called your Initial Enrollment Period. This is a seven-month window: the three months before you turn 65, your birthday month, and the three months after. If you are still working and have "creditable"insurance (insurance from a job that is considered as good as Medicare), you have a choice.

If your company is small (fewer than 20 people), Medicare usually becomes your primary insurance the day you turn 65, meaning you must sign up then to avoid big gaps in coverage and future late fees. If your company is large, you can delay Part B (the part that covers doctor visits and has a monthly premium) until you actually retire. Once you stop working or lose that job-based insurance, you get an eight-month Special Enrollment Period to sign up. Just be careful:if you have a Health Savings Account (HSA), you usually need to stop contributing to it six months before you sign up for Medicare to avoid tax headaches.

Related Medicare Resources

Smiling elderly couple on social security benefits misunderstand medicare advantage are outdoors with man presenting a bouquet of yellow flowers to the woman.Smiling elderly couple disappointed at their doctor for not accepting medicare sitting on a bench outdoors holding a colorful bouquet of flowers.A group of six older adults enjoy discussion with primary care physician covered by medicare sitting together indoors, smiling and enjoying conversation with drinks.
Two elderly men in a nursing home paid for by medicare sitting at a wooden table outdoors, one showing the other something on a tablet, with drinks on the table.

In 

 specifically

In Utah, many of our neighbors work well past 65,especially in our thriving tech and healthcare sectors along the Wasatch Front.If you work for one of Utah's large employers—like Intermountain Health, the University of Utah, or even the State—their benefits offices are very familiar with "coordinating" with Medicare. It is always a good idea to chat with your HR person. They can provide you with a specific form (the CMS-L564)when you finally do retire to prove you had coverage, which keeps the"Medicare police" from charging you late fees.

What this means for you

For you, this means flexibility. You don't have to rush into paying for Part B premiums (which are $202.90 a month for most people in 2026) if you already have great insurance at work. It gives you time to compare your current work plan against Medicare to see which one actually saves you more on your prescriptions and doctor visits.

Related Questions

Still have questions about Medicare?

Book a review with a licensed Medicare advisor.

Senior couple sitting together outdoors near white flowers and greenery, smiling and looking to the right.