Your Initial Enrollment Period is seven months wide, but missing the right window inside it can mean permanent penalties. Here’s the timeline broken down simply, plus what to do if you’re still working.
Published June 10, 2026 · By Tom Wertish, Options.Health
Turning 65 comes with a stack of mail you didn’t ask for — postcards from Medicare Advantage carriers, calls from numbers you don’t recognize, and a real deadline buried somewhere in the middle of it. Here’s the part that actually matters: the window around your 65th birthday, what happens if you miss it, and where to look next once you’re past it.
Your Initial Enrollment Period (IEP) is seven months wide: the three months before your birthday month, your birthday month itself, and the three months after. This is the cleanest window you’ll ever get to sign up for Medicare Part A and Part B.
Enroll in the three months before your birthday and coverage starts the month you turn 65. Wait until your birthday month or later, and your start date pushes back — which matters if you’re dropping other coverage and don’t want a gap.
The moment you’re 65 or older and enrolled in Part B, a separate six-month clock starts: your one-time Medigap Open Enrollment Period. During this window, Minnesota law guarantees you access to a Medigap (Medicare Supplement) plan — no health questions, no denial for pre-existing conditions.
Miss it, and you can still apply for Medigap later, but insurers are allowed to medically underwrite you at that point. If you’re leaning toward a Medigap plan instead of Medicare Advantage, this window is the one to plan around — not something to revisit “eventually.”
The most common misstep isn’t missing the window entirely — it’s still working at 65 and assuming Medicare can wait indefinitely without a penalty. It often can, but only under specific conditions: your employer coverage has to come from an employer with 20 or more employees, and it has to be considered creditable coverage.
Get this wrong and the penalty is permanent: Part B premiums can rise 10% for every full year you delayed without qualifying coverage, for as long as you have Part B. It’s a five-minute phone call to confirm before you decide — worth making before you assume you’re covered.
Tell us a little about your situation and a licensed Options.Health broker will follow up, usually within one business day.
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