First Time Medicare
Operated by HealthBenefitsCompass LLC, a subsidiary of HealthcareGPS Inc.Medicare education · Not a government websiteReviewed by Lauri Middleton, RN, MSN (licensed Medicare agent) and Karen OrillaHow we prepare our guidance →Meet our reviewers →

Reviewed for accuracy by Lauri Middleton, RN, MSN, licensed Medicare agentReviewed for clarity by Karen OrillaMeet our reviewers →

Working past 65

Working past 65

Four things decide whether waiting on Part B is safe: whether the coverage comes from a current job, how big the employer is, whether an HSA is still being funded, and what happens to drug coverage. Answer them on the calendar and this page reads back the consequences.

The calendar has no job-coverage answer yet. Start on the home page and choose "coverage from a current job" to see this page filled in.

Start my calendar

Ask a real person

Ask the benefits office:
  1. Is this coverage based on current employment?
  2. How many employees does the employer have — 20 or more?
  3. Is the drug coverage creditable? In writing, please.
  4. When I leave, will you give me a letter with the coverage end date?
Ask Social Security:
  1. If I delay Part B, what form do you need from my employer when I sign up later?
  2. Can I take Part A now and Part B later — and what does that do to my HSA?
Decision 1 of 5 →

The rules we use

Leaving job coverage opens an eight-month window

If you or your spouse are still working and you have health coverage from that job, you can sign up for Part B later without a penalty. The window is eight months, starting the month after the job or the coverage ends — whichever comes first. COBRA and retiree coverage do not count as coverage from a current job.

Source: Medicare.gov — Working past 65 · In effect since 2023-01-01 · Last checked 2026-09-06

Employer size decides who pays first

With 20 or more employees, the job plan pays first and Medicare second, so delaying Part B is usually safe while that coverage lasts. With fewer than 20, Medicare pays first — and if you have not signed up, the job plan may pay very little.

Source: Medicare.gov — Working past 65 · In effect since 1986-01-01 · Last checked 2026-09-06

HSA contributions must stop before Part A

Part A can be backdated up to six months when you sign up after 65. Contributions made for any month you have Part A are not allowed, so the safe stop is six months before the month you plan to apply — but never earlier than your eligibility month.

Source: Medicare.gov — Working past 65 · IRS Publication 969 · In effect since 2004-01-01 · Last checked 2026-09-06

Drug coverage: two months after job coverage ends

The Part D window after losing job-based drug coverage is shorter than the Part B one: two months after the coverage ends. Ask the benefits office for a letter saying whether the drug coverage was creditable.

Source: Medicare.gov — Special Enrollment Periods · In effect since 2006-01-01 · Last checked 2026-09-06