Retiring after 65? Put these dates on one page

Ask the benefits administrator first

Confirm whether coverage is based on current employment, which insurance pays first, and when coverage ends. Ask what a change means for dependents. Do not cancel existing coverage before confirming the next arrangement.

Separate the deadlines

Eligible people generally have an eight month Part B Special Enrollment Period after employment or related coverage ends, whichever comes first. Waiting can still cause a coverage gap. Drug coverage has separate timing rules. COBRA does not restart or extend the Part B window.

Bring the HSA into the conversation

Medicare affects HSA contribution eligibility, and Part A may be retroactive. Medicare advises stopping contributions, including employer contributions, six months before retiring or applying for Social Security or Railroad Retirement benefits. Confirm your timing with your benefits administrator and a qualified tax professional.

Make a handoff sheet

Use four lines: last day of work, employer coverage end date, Medicare effective dates, and new plan effective date if applicable. Add who confirmed each. Save employer coverage evidence and creditable drug coverage notices.

Go straight to the source

• Working past 65
• COBRA and Medicare

Sources checked September 28, 2026. General education, not a coverage determination or medical advice. Plan terms, eligibility, and state rules can vary. How we approach education