Medicare · Guide
Working past 65
If you’re still working at 65, you usually don’t have to rush into Medicare — but whether you enroll, delay, or do a mix depends on your employer’s size, your HSA, and your drug coverage. These guides walk through each decision so you don’t accidentally trigger a lifelong penalty.
Turning 65 doesn’t mean you have to drop everything and enroll in Medicare. If you’re still working, you can often delay parts of it without penalty — but the rules are unforgiving, and a wrong assumption can cost you for the rest of your life. The biggest factor is your employer’s size: with 20 or more employees you can usually wait on Part B, while a smaller employer means you should enroll at 65. From there, your HSA, your drug coverage, and how you handle COBRA all shape the timing. The guides below take each decision one at a time.
The decisions, one at a time
Medicare and your HSA
Why enrolling in any part of Medicare, even free Part A, ends HSA contributions.
Read more →Medicare and employer coverage
The 20-employee rule that decides whether you can delay Part B.
Read more →The COBRA trap
Why COBRA isn't active coverage, and the penalty it can cause.
Read more →Part B Special Enrollment Period
The eight-month, penalty-free window to enroll when you retire.
Read more →Creditable drug coverage at work
When employer drug coverage lets you delay Part D safely.
Read more →When to enroll when you retire
Timing the handoff from work coverage to Medicare with no gap.
Read more →Where this fits
These guides build on the basics in the Eligibility & Enrollment pillar. If you just want the short answer on whether you can wait, start with do I have to enroll at 65 if I’m still working? or do I need Medicare if I have employer insurance? When you’re ready to put a plan in place, you can compare the options available where you live.
Ready to compare?
Ready to compare plans for your retirement?
Enter your ZIP and we’ll take you to PlanMatch Medicare to compare the 2026 plans available where you live.