The questions everyone has
Questions, answered plainly.
When exactly do I sign up?
Your personal enrollment window is built around your 65th birthday: it opens three months before your birthday month and closes three months after it. Signing up early in the window means coverage is ready when you are. Tell me your birth month and I’ll tell you your exact dates — that’s a one-minute call to 1-888-808-8282.
Do I have to sign up if I’m still working at 65?
Maybe not — but don’t guess. If your employer’s plan qualifies, you can often delay without penalty. Whether it qualifies depends on things like company size, and COBRA or retiree coverage usually doesn’t count. Guessing wrong creates a permanent penalty, so this is the one question you should never answer for yourself. Call 1-888-808-8282 first.
What happens if I miss my deadline?
Two things, and neither is good: your monthly Part B premium can go up permanently — 10% for every full year you were late — and you may wait months for another chance to enroll, uncovered in the meantime. If you think you’re late or close to it, call 1-888-808-8282 today and we’ll figure out where you actually stand.
What’s the difference between Medicare Advantage and a Supplement?
Two different philosophies. An Advantage plan replaces how you receive Medicare: one private plan, usually with drug coverage built in, generally with a network of doctors. A Supplement works alongside Original Medicare and helps pay what Medicare doesn’t, with no network — any doctor who takes Medicare. One usually costs less per month; the other buys more freedom. Which is right depends on your doctors, your prescriptions, and your budget — that’s the conversation.
Does Medicare cover dental?
Original Medicare generally does not cover routine dental care, and the same goes for routine vision and hearing. Some private plans include coverage for those; what’s included and what it’s worth varies plan to plan, and it should never be the first reason you pick a plan. We’ll weigh it honestly on the call.
What if my spouse is younger than me?
Medicare covers one person at a time — there’s no family plan. When you move to Medicare, a younger spouse who was on your employer coverage needs their own plan until they turn 65. That transition has real options and real deadlines of its own, and it belongs in the same phone call as your enrollment: 1-888-808-8282.
Will I lose my doctor?
Not if we do this right. With Original Medicare plus a Supplement, you can see any doctor in the country who accepts Medicare. With an Advantage plan, your doctors need to be in the plan’s network — so the first thing I do is check your doctors against any plan we discuss, before anything gets signed.
What does it cost me to use an agent?
Nothing. When you enroll through an agent, the insurance company pays the commission — your premium is exactly the same as if you’d signed up on your own. You’re not paying extra for the help; you’re just choosing whether to get it.
I live in New York. Is anything different here?
Yes — something genuinely good. New York is a community-rated state with continuous open enrollment for Medicare Supplement plans. In plain English: in New York, a Supplement plan can’t charge you more because of your age, and can’t turn you down or price you up because of your health history — protections most other states don’t give you. It changes the math on the Advantage-versus-Supplement decision, and most New Yorkers turning 65 have never heard it. Worth a conversation: 1-888-808-8282.
What should I have ready when I call?
Nothing formal. Knowing your doctors, your prescriptions, and what coverage you have now makes the twenty minutes count — but if all you have is your birthday and your questions, that’s enough to start.
By calling the number above, you will be connected to a licensed insurance agent. Monday–Friday, 9am–5pm ET.