When should I sign up for Medicare if I'm still working at 65?

If you have credible employer coverage from a company with 20+ employees, you can usually delay Part B without a late penalty. Most people enroll in premium-free Part A at 65, then delay Part B until they leave that employer plan and use an 8-month Special Enrollment Period. If the employer has fewer than 20 employees, Medicare becomes primary — enroll in both A and B during your Initial Enrollment Period (3 months before to 3 months after your 65th birthday month).

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Turning 65

When to sign up for Medicare if you're still working

If you're approaching 65 and still covered by an employer plan, here's how to coordinate enrollment so you avoid late penalties and gaps in coverage.

Your enrollment window

Your Initial Enrollment Period (IEP) is 7 months long: the 3 months before your 65th birthday month, your birthday month, and the 3 months after. For most people that's the safe default window for Parts A and B.

3 months before: enroll in Part A (premium-free for most); decide on Part B based on your employer plan.
Birthday month: coverage starts the 1st of the month you turn 65 if you enrolled early.
3 months after: last chance to enroll without using a Special Enrollment Period.

Still working at 65? Checklist

✅ Confirm whether your employer has 20+ employees — if yes, employer plan is primary and you can usually delay Part B without penalty.
✅ If under 20 employees, Medicare is primary — enroll in both Part A and Part B during your IEP.
✅ Ask HR for a written "creditable coverage" letter — you'll need it to avoid Part D late penalties later.
✅ Enroll in premium-free Part A at 65 (unless you contribute to an HSA — Part A stops HSA contributions).
✅ When you leave the employer plan, use your 8-month Special Enrollment Period for Part B and a 63-day window for Part D.
✅ Compare Medigap Plan G, Plan N, and MAPD before your employer coverage ends.