Still Working at 65? Medicare Checker
Four questions. The tool matches your situation to the published rules: whether you can delay Part B without penalty, when your window opens, and the HSA and Social Security traps to avoid.
Your situation at 65
1. Where does your health coverage come from?
2. How many employees does that employer have?
3. Are you contributing to a health savings account (HSA)?
4. Will you start Social Security at or before 65?
What the rules say
The rules behind the checker
| Rule | ●Employer plan, 20+ employees | ●Employer plan, under 20 | ●COBRA / retiree / marketplace |
|---|---|---|---|
| Can you delay Part B without penalty?Only current employment coverage stops the penalty clock. | Yes | NoMedicare pays first; enroll at 65. | NoNot current employment. |
| Who pays first?Decides whether skipping Part B leaves you exposed. | Employer plan | Medicare | Medicare (once eligible) |
| Special Enrollment Period later?8 months from the end of employment or coverage. | Yes | Only via the job | No |
| Counts as creditable drug coverage?Stops the Part D penalty clock. | Ask HRMost large plans are; get the notice. | Ask HR | Depends |
| HSA contributions allowed?Any Medicare enrollment, including Part A, ends eligibility. | Only if no Part A | No | No |
TRICARE For Life requires Part B at 65. VA care does not count as creditable for Part B.
Sources
- Medicare.gov, "Avoid late enrollment penalties"
- Medicare.gov, "When does Medicare coverage start?"
- IRS Publication 969, Health Savings Accounts (Medicare and HSA eligibility; retroactive Part A)
- CMS, Medicare Secondary Payer rules (20-employee threshold)
- Form CMS-L564, Request for Employment Information
- TRICARE For Life eligibility
This tool is educational and simplifies by design. It computes published Medicare rules for the inputs you enter; it does not know your full situation, is not insurance, tax, or legal advice, and does not recommend any action. Nothing you type is transmitted or stored — the math runs in your browser. Confirm your dates and amounts with Social Security (1-800-772-1213), Medicare (1-800-MEDICARE), or a licensed professional before acting.
Still-working questions, answered
How do I know if my employer has 20 or more employees?
The count is employees on the payroll for 20 or more weeks in the current or prior calendar year, not people enrolled in the plan. Ask HR for it in writing; you will also need the employer to complete form CMS-L564 when you enroll later.
Can I keep my employer plan and take Part A only?
Usually yes, and premium-free Part A costs nothing. The exception is an HSA: any Part A enrollment ends your ability to contribute, and Part A is backdated up to six months if you enroll after 65.
My spouse is still working. Does that count for me?
Yes, if the coverage is from your spouse’s current employment and the employer has 20 or more employees. Coverage through a domestic partner does not qualify.
I have COBRA from my old job. Am I safe to wait?
No. COBRA is not current employment. Your Part B deadline is your Initial Enrollment Period (or the 8 months after the job ended, if that is later). COBRA also pays second to Medicare once you are eligible, whether or not you enrolled.
I’m a veteran with VA care. Do I need Part B?
VA coverage does not count as creditable for Part B, so the penalty applies if you enroll later. Many veterans take Part B for care outside the VA. TRICARE For Life is different: it requires Part B at 65.
Related tools and guides
Enrollment window calculator
Your Special Enrollment Period end date from the day coverage stops.
Open the tool →Income surcharge calculator
Working past 65 usually means higher income; see what it does to your premium.
Open the tool →
Talk it through before you decide
Bring your birth date, your work situation, and last year’s tax return. Leave knowing your enrollment window, what Medicare will cost you, and whether the income surcharge applies.
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