Medicare · Resource

Turning 65 in Jackson Hole: the Medicare timeline, in order

By Heather Huhn, Licensed Independent Insurance Agent (NPN 19222086) · Updated September 5, 2026 · Jackson Hole, Wyoming

Short version: your first Medicare window is seven months long and opens three months before the month you turn 65. Sign up in those first three months and coverage starts the month you turn 65; sign up during or after that month and it starts the month after. If you keep working with employer coverage, a different window applies. Here is the whole timeline, in order, with every date from Medicare’s own rules.

When does my Initial Enrollment Period start and end?

It lasts seven months: the three months before the month you turn 65, that month, and the three months after. Coverage always starts on the first of a month. Sign up in the three months before and Part B starts the month you turn 65. Sign up during the month you turn 65 or in the three months after and it starts the month after you sign up — a rule that changed on January 1, 2023, when CMS ended the old two-to-three-month delay.

Premium-free Part A starts the month you turn 65 regardless of when in the window you sign up. If you were born on the first of the month, it starts the month before.

Will I be enrolled automatically?

Yes, if you are already receiving Social Security or Railroad Retirement benefits at least four months before you turn 65. Part A and Part B start on their own and the welcome package with your Medicare card arrives three months before coverage begins. If you are not yet drawing benefits — which is most people still working in Teton County at 64 — you sign up through Social Security, and the card arrives about two weeks later.

What if I keep working past 65?

It depends on the size of the employer. If the group health plan comes from an employer with 20 or more employees, the plan pays first and Medicare pays second, so you can delay Part B while you are covered. When the employment or the coverage ends, whichever comes first, an eight-month Special Enrollment Period opens for Part B with no penalty. COBRA does not count as employer coverage for this purpose and does not extend the eight months.

If the employer has fewer than 20 employees, Medicare pays first. Job-based coverage from a small employer may not pay for services unless you have both Part A and Part B, so for most people in that position the answer is to enroll on time. Many Jackson Hole employers are under 20, which makes this the first question we ask.

What are the penalties if I sign up late?

Part B: an extra 10% of the premium for each full twelve-month period you could have had Part B and did not, added for as long as you have Part B — for most people, a lifetime. Part D: an extra 1% of the national base beneficiary premium for each month you go without creditable drug coverage after a 63-day gap, added for as long as you have Medicare drug coverage, even if you change plans.

If you miss your Initial Enrollment Period and have no Special Enrollment Period, the General Enrollment Period runs January 1 through March 31 each year, with coverage starting the month after you sign up.

When can I buy a Medigap plan without health questions?

Federal law gives you a six-month Medigap Open Enrollment Period that starts the first month you have Part B and are 65 or older. During that window an insurer must sell you any Medigap policy it offers and may not use medical underwriting to turn you down or charge more for a pre-existing condition. It is a one-time window that does not repeat each year, which is why the Part B start date is worth planning around.

I have an HSA. When do I stop contributing?

Your HSA contribution limit is zero beginning with the first month you are enrolled in any part of Medicare, and that includes months of retroactive coverage. When you apply for Part A after 65, coverage can be backdated up to six months, though never earlier than the month you turned 65. Medicare’s guidance is to stop HSA contributions six months before you apply for Medicare or for Social Security benefits (IRS Publication 969; medicare.gov).

What happens every year after that?

The Annual Enrollment Period runs October 15 through December 7, and changes take effect January 1. Anyone already on a Medicare Advantage plan also gets the Medicare Advantage Open Enrollment Period, January 1 through March 31, to switch plans or return to Original Medicare. A Medicare Advantage plan requires both Part A and Part B; a stand-alone drug plan requires Part A or Part B.

The timeline, in one list

  • Six months before you plan to apply: stop HSA contributions if you will be enrolling in Part A.
  • Three months before the month you turn 65: the Initial Enrollment Period opens. Automatic enrollees receive the card now.
  • The month you turn 65: Part A starts. Part B starts too if you signed up in the three months before.
  • The first month you have Part B, at 65 or older: the six-month Medigap Open Enrollment Period begins.
  • Three months after the month you turn 65: the Initial Enrollment Period closes.
  • 63 days without creditable drug coverage: the Part D penalty clock starts.
  • Working past 65 with a 20-plus employer: eight months from the end of employment or coverage to enroll in Part B without penalty.
  • Every year, October 15 to December 7: the Annual Enrollment Period.

Where do I get help in Wyoming?

Wyoming had 127,403 Medicare beneficiaries in 2024, and 82% of them were on Original Medicare rather than a Medicare Advantage plan (KFF). The Wyoming State Health Insurance Information Program, the state’s federally funded SHIP, offers one-on-one counseling at (800) 856-4398 from its office in Riverton. Social Security handles enrollment at 800-772-1213.

Huhn Insurance is a licensed independent agency in Jackson Hole. We compare Original Medicare with a Medigap plan against the Medicare Advantage and Part D plans sold in your county, check your doctors, hospital and prescriptions against each option, and stay on the file after you enroll — by phone, by video or at 170 E Broadway in Jackson, and for Star Valley and Teton Valley, Idaho as well. Read more on our Medicare page, meet Heather, pick a time, or call 307-284-3060.

Questions people ask

Do I have to sign up for Medicare at 65 if I am still working?

Not always. With coverage from an employer of 20 or more employees, the group plan pays first and you can delay Part B without penalty, then use an eight-month Special Enrollment Period when the job or the coverage ends. With an employer under 20 employees, Medicare pays first, so most people in that position enroll in Part A and Part B on time.

How long is the Medicare Initial Enrollment Period?

Seven months: the three months before the month you turn 65, that month, and the three months after. Sign up in the first three months and Part B starts the month you turn 65. Sign up during or after that month and it starts the month after you sign up. Premium-free Part A starts the month you turn 65 either way.

Can I get a Medigap policy with a pre-existing condition?

Yes, during your Medigap Open Enrollment Period — the six months that start the first month you have Part B at 65 or older. In that window an insurer must sell you any Medigap policy it offers and may not use your health history to refuse you or raise the price. Outside the window, medical underwriting can apply, so the Part B start date is worth planning around.

Do you charge for Medicare help?

Carriers build our commission into the plan, so you pay the same premium whether you enroll on your own or with us. Medicare commissions are set by CMS and paid by the carrier. How we are paid is disclosed in writing up front.

Sources

All dates and rules read from the sources above on September 5, 2026. This page is general information, not legal or tax advice. Not affiliated with Medicare or any government agency. We do not offer every plan available in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.