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Retiring after 65? Get your next steps in order.

Coordinate the end of employer coverage with your Medicare questions.

Confirm the employer coverage end date

Your last workday and the date your health coverage ends may differ. Ask your benefits administrator for the exact date and the documents you may need. Tell the licensed insurance agent whether you already have Medicare Part A, Part B, or other coverage.

Check enrollment timing before making changes

Current employment coverage, retiree coverage, and COBRA are not interchangeable for Medicare enrollment purposes. Your next steps depend on the type of coverage and your circumstances. Confirm your timing with Social Security or Medicare.

Build a transition checklist

  • Employer coverage end date and benefits contact.
  • Current Medicare enrollment details.
  • Coverage needs of a spouse or dependents.
  • Doctors, prescriptions, and pharmacy list.
  • Questions about applications, effective dates, and next steps.

Outside a local licensed insurance agent’s area? You can still use these guides and call with questions.

Official resourcesWorking past 65

Educational content prepared September 12, 2026. Individual circumstances and plan details need review.

Health Plan Assistants is a DBA of Medicare Assistant LLC, a licensed health insurance agency. The purpose of this site is the solicitation of insurance. Contact may be made by an insurance agent/producer or insurance company. Health Plan Assistants is not connected with or endorsed by the U.S. government or the federal Medicare program. We offer plans from a number of insurance companies. Plan availability and licensed insurance agent services vary by location.

We do not offer every plan available in your area. For information on all of your options, contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP).

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