Sometimes yes, and it can save you real money. But the rule turns on one word, and getting it wrong is permanent.
Key takeaways
- You can generally delay Part B without penalty if you have group coverage through current employment, yours or your spouse's.
- COBRA, retiree coverage and Marketplace plans do not count, and at employers under 20 people Medicare usually pays first.
- Confirm in writing which plan pays first, stop HSA contributions six months before enrolling, and file CMS-40B with L564 within eight months.
What's the short answer?
If you have group health coverage through current employment — yours or your spouse's — you can generally delay Part B without a penalty, and enroll later through a Special Enrollment Period.2
What counts as qualifying coverage?
Group health coverage based on someone actively working. If the employer has 20 or more employees and the coverage is based on current employment, their plan generally pays first and Medicare second.5 That payer order is what makes delaying Part B safe. Employer size alone does not settle it: confirm that the plan pays first, that the coverage is tied to current employment, and that its drug coverage is creditable, so you are not exposed to the Part D penalty.
What does NOT count?
- COBRA — not current employment.
- Retiree coverage — not current employment.
- Marketplace plans.
- VA coverage alone, for Part B purposes.
Delaying on any of these earns you the penalty anyway. This is the single most expensive misunderstanding in Medicare.
Should you still take Part A?
Most people have premium-free Part A at 65, and taking it alongside employer coverage generally costs nothing in premiums. It is not free of tax consequences: once you have Part A you can no longer contribute to a Health Savings Account, and that applies to the months Part A is backdated too.4
What is the HSA exception?
How does your 8-month clock work?
When employment or the coverage ends — whichever comes first — you have eight months to enroll in Part B penalty-free.2 Note that it starts with the job ending, not when COBRA runs out. People lose this window waiting for COBRA to expire.
Part D is different and tighter. The late enrollment penalty is triggered by going 63 days or more without creditable drug coverage after your enrollment opportunity ends.6 That is a trigger, not a grace period: line up drug coverage before the gap opens, and check when the new coverage actually takes effect. If you qualify for Extra Help, the penalty does not apply.
What should you do next?
- Confirm your employer size and which plan pays first — in writing.
- If you have an HSA, plan the six-month stop before enrolling.
- Get CMS-L564 signed by HR before your last day.3
- File CMS-40B plus L564 within the eight-month window.
Sources
- medicare.gov — Medicare & You 2026
- medicare.gov — Working past 65
- cms.gov — CMS-L564 Request for Employment Information
- IRS Publication 969 — Health Savings Accounts
- medicare.gov — When can I sign up for Medicare
- medicare.gov — Avoid late enrollment penalties
Do I Have to Sign Up for Medicare at 65?
The working-past-65 checklist, the forms, and the deadlines that carry lifetime penalties.
The Social Security PlaybookWhen to claim, how to protect a spouse, and the 75 questions people actually ask. By Kwame Kuadey.About the book →Next Chapter Today is not a government website and is not affiliated with the Social Security Administration or any agency. This article is educational and is not individualized legal, medical, tax or financial advice. Confirm your own figures with the agency before you act.
