Plain-language Medicare guidance • Enrollment windows • Clear decisions.

Annual Enrollment opens October 15 25 days away — a review now beats a rush later
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Medicare • Retirement Guidance
← Medicare, explained

When to Enroll

Medicare runs on windows. Know yours, and every other decision gets easier — miss it, and some penalties never leave.

Your Initial Enrollment Period

Your first window lasts seven months: the three months before your 65th birthday month, your birthday month, and the three months after. Enrolling in the early months means coverage starts the month you turn 65.

Working past 65

If you (or your spouse) are still working and covered by a qualifying employer plan, you can usually delay Part B without penalty — and you get an eight-month Special Enrollment Period when that employment coverage ends. The rules differ for small employers, COBRA does not count as employer coverage, and contributing to an HSA while enrolled in any part of Medicare is not allowed — three details that catch more people than any others.

The annual rhythm

Every fall, the Annual Enrollment Period (October 15 – December 7) lets anyone change Advantage or drug plans for January 1. Advantage members get one more adjustment window early in the year. Plans change their costs and formularies every single year — which is why a plan that fit last year deserves ten minutes of review this year.

The penalties, so you never meet them

Part B: roughly 10% added to your premium for each full 12-month period you could have had it and did not — for as long as you have Part B. Part D: about 1% per month, also permanent. Both are entirely avoidable with a calendar and a short conversation.

Educational information, not advice about any specific plan. For details on every option available in your area, visit Medicare.gov or call 1‑800‑MEDICARE.