Medicare enrollment

When can I enroll in Medicare?

Your Initial Enrollment Period is seven months long: the three months before the month you turn 65, your birthday month, and the three months after. Enrolling in the three months before your birthday month is what starts coverage on the first day of that month.

  • Initial Enrollment Period: seven months, centered on your 65th birthday month.
  • Born on the 1st of the month? Medicare treats your birthday as the previous month, and the whole window shifts a month earlier.
  • General Enrollment Period: 1 January – 31 March, for anyone who missed their window.
  • Annual Enrollment Period: 15 October – 7 December, to change Medicare Advantage or Part D for the following year.
  • Still working past 65 with employer coverage? A Special Enrollment Period usually applies instead.

The seven-month window

The Initial Enrollment Period opens three months before your 65th-birthday month and closes three months after it. When coverage actually begins depends on where in that window you sign up: enroll in the three months before your birthday month and coverage starts on the first of your birthday month; enroll during or after it and coverage starts the first of the month after you sign up. Signing up early is what avoids a gap.

One detail catches people every year: if you were born on the first of a month, Medicare treats your birthday as falling in the previous month. Eligibility, the window and the coverage date all shift a month earlier.

If you are still working at 65

If you or your spouse are still working and covered by an employer group plan, you may be able to delay Part B without a penalty, then take a Special Enrollment Period when that coverage ends. This is where the rules turn on details that are easy to get wrong — the size of the employer matters, COBRA and retiree coverage do not count the same way active employment does, and the Part D clock runs separately from the Part B clock.

Getting this wrong is expensive and largely irreversible, so it is worth a conversation rather than a guess. There is no cost to ask.

The windows after your first one

If you miss your Initial Enrollment Period, the General Enrollment Period runs 1 January to 31 March, with coverage starting the month after you sign up — and a late-enrollment penalty may apply. Separately, the Annual Enrollment Period from 15 October to 7 December is when anyone already on Medicare can change Medicare Advantage or Part D plans for the coming year, and the Medicare Advantage Open Enrollment Period from 1 January to 31 March allows one further change for people already in an Advantage plan.

A qualifying life event — moving out of a plan’s service area, losing other coverage, a change in Extra Help status — can open a Special Enrollment Period at any time of year.

This is not a complete list of Special Enrollment Periods. Visit Medicare.gov for the full list.

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FAQ

Related questions

When can I enroll in Medicare?

Your Initial Enrollment Period is seven months long: the three months before the month you turn 65, your birthday month, and the three months after. Enrolling in the three months before your birthday month is what starts coverage on the first day of that month.

What does it cost to work with CUPS Insurance on Medicare enrollment?

Nothing. Carriers pay a commission when a plan is issued, and that commission is already built into the plan price whether you use an agent or not.

Buying the same plan on your own does not make it cheaper — it just means nobody checked your doctors and prescriptions first, and nobody picks up the phone in March when something goes wrong.

Does CUPS Insurance offer every plan available for Medicare enrollment?

No, and no agency does. We are independent, which means we compare across the carriers listed on this site rather than representing a single one — but that is not the same as offering every plan on the market.

We do not offer every plan available in your area. Currently we represent 8 organizations which offer 72 products in your area. Please contact Medicare.gov, 1-800-MEDICARE to get information on all of your options.

Who will actually be helping me?

Sarah Wood Rodriquez, licensed since 2009 — over 17 years — and licensed in Utah, Arizona, Idaho. NPN 14943086.

The person who answers the phone is the person who reviews your plan. There is no call center and no handing you between departments.

How do I get started with Medicare enrollment?

Call Sarah, a licensed insurance agent, at 435-292-8777 (TTY 711) or book a call. The first conversation usually runs twenty to thirty minutes and there is nothing to sign.

Bring your prescription list and your doctors’ names — with those, the comparison can be a real one rather than a generic one.

What happens after I enroll?

She stays your agent. If a prescription moves tier, a doctor leaves the network, or a letter arrives that makes no sense, you call the same number and speak to the same person.

Every autumn your plan gets reviewed before Open Enrollment, because plans change even when your health does not. On Medicare enrollment that matters as much as the original enrollment.

Do we have to meet in person?

No. Most conversations happen by phone or video, which is faster for most people. If you would rather meet face to face, the office is at 3293 Harrison Blvd #213, Ogden — by appointment only, so call before you come.

Hours are 10:00 AM – 5:00 PM, Monday to Friday.

Can I do all of this in Spanish?

Yes. The whole site is available in Spanish and English, and appointments, paperwork and follow-up can be handled in Spanish from start to finish.

If you would rather talk in Spanish, say so when you call Sarah, a licensed insurance agent, at 435-292-8777 (TTY 711) and it is handled that way from the first conversation.

Grab a cup. Let's make insurance make sense.

A real conversation with a licensed agent who will check your doctors and prescriptions before you decide — and answer the phone all year after that.

Book a call with Sarah Call 435-292-8777 Speak with a licensed insurance agent · TTY 711

Office hours: 10:00 AM – 5:00 PM · Ogden, Utah · NPN 14943086