Getting started
Retiring after 65? Put these dates on one page
Line up your employer coverage, Medicare, and savings account timing before your last day at work.
Confirm when employer coverage ends, which enrollment rules apply, and whether HSA contributions must stop before Medicare starts. COBRA does not extend your Part B enrollment window.
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.
Make it useful
Your next step checklist
Use this here, or print it for your next conversation. Your checks stay on this page only.