Working Past 65: Do You Need Medicare?

You may be able to delay Part B without a penalty, but only after you verify what kind of employer coverage you actually have.

Written and reviewed by James KauferIndependent Medicare Agent · NPN 15374945Updated August 19, 2026

The answer depends on the coverage, not your birthday

Turning 65 does not automatically mean every working person should enroll in every part of Medicare immediately. The critical questions are whether your health insurance is based on your or your spouse’s current employment, how many employees the employer has, whether the coverage is considered creditable for drug coverage, and whether you contribute to an HSA.

Employer size can change who pays first

If you are 65 or older and covered through current employment, the employer’s size can affect whether the group plan or Medicare pays first. Medicare specifically tells people with coverage from an employer with fewer than 20 employees to check whether they need Parts A and B because the employer plan might not pay correctly without Medicare.

James Kaufer reviewing Medicare enrollment information for someone working past 65
Working past 65 is an enrollment-timing problem before it is a plan-selection problem.

The Part B Special Enrollment Period

If you qualify to delay Part B because of current-employment coverage, you can generally enroll while the coverage continues or during the eight-month Special Enrollment Period after the employment or job-based coverage ends, whichever happens first.

COBRA is not a substitute for understanding the Part B clock

COBRA can continue employer coverage temporarily, but the Part B Special Enrollment Period is tied to current employment. Medicare says the eight-month clock can begin when the job or active job-based coverage ends even if you elect COBRA.

HSA contributions require special attention

Medicare advises people with HSAs to stop contributions six months before retiring or applying for Social Security or Railroad Retirement Board benefits. Premium-free Part A can start retroactively, creating tax problems if HSA contributions overlap Medicare coverage.

Frequently asked questions

Can I keep employer coverage and delay Part B?

Often yes if you or your spouse have qualifying group health coverage based on current employment, but you should verify how the employer plan coordinates with Medicare before delaying.

What if the employer has fewer than 20 employees?

Medicare warns that job-based coverage may not pay correctly if you do not have Part A and Part B when the employer providing coverage has fewer than 20 employees.

What should I know about an HSA?

Medicare advises people with an HSA to stop contributions six months before they retire or apply for Social Security or Railroad Retirement Board benefits because premium-free Part A can be retroactive.

Primary sources

This guide is based on current information from Medicare.gov and CMS. Rules can change, so verify time-sensitive details before acting.