Guide

Medicare & Working Past 65

How Medicare works with employer coverage

Michael Furman
Reviewed by Michael Furman, COO — 24 years in insurance · MDRT Top of the Table
NovaVida Group licensed team · Updated August 2026

Still working at 65 with employer health coverage? You may be able to delay parts of Medicare without penalty — but the rules depend on your employer’s size, and getting it wrong can be costly. Here’s how to coordinate both.

It Depends on Employer Size

If your employer has 20 or more employees, its plan generally pays first and you can usually delay Part B without a penalty, then enroll later through a Special Enrollment Period when you retire. If the employer has fewer than 20 employees, Medicare often becomes the primary payer, so enrolling on time is important to avoid gaps.

Watch Out for HSAs and Drug Coverage

Once you enroll in any part of Medicare, you can no longer contribute to a Health Savings Account. And you’ll want to confirm your employer drug coverage is “creditable” so you don’t face a Part D penalty later. We help you time it all correctly.

Fast Facts

  • Employer with 20+ employees: you can usually delay Part B
  • Employer under 20: Medicare often pays first — enroll on time
  • Most people still take premium-free Part A at 65
  • Losing employer coverage opens a Special Enrollment Period

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Frequently Asked

Should I take Part A at 65 if I’m still working?

Usually yes, since it’s premium-free for most people — unless you’re contributing to an HSA, in which case enrolling in Part A ends your HSA contributions. It’s a common trade-off we help clients weigh.