Retiring After 65
Pending review by Liz McPherson, licensed insurance agent since 2007 · Updated September 25, 2026
You'll apply for Part B (and Part A if you don't already have it) through Social Security using a Special Enrollment Period, with a form from your employer confirming your coverage. Start about 2–3 months before your coverage ends so there's no gap.
When your job or your employer coverage ends, whichever comes first, you generally have 8 months to sign up for Part B without a late penalty. You'll usually submit two forms: -40B (the Part B application) and CMS-L564 (completed by your employer to show you had group coverage). These can be submitted online through Social Security, by mail, or in person. Once your Part B start date is set, you'll have a shorter window, generally 2 months, to choose a Medicare Advantage or Part D plan, or you can add a Medicare Supplement. doesn't count as coverage from current work, so it doesn't extend the 8-month window.[LIZ REVIEW]
Whether you already have Part A, whether you have an , whether your employer can complete the -L564 easily, and whether you want Medicare Advantage or a Supplement.
Every situation is a little different. Call us at 719-358-6696 — we actually answer the phone — or book a no-cost appointment.
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