Most Medicare mistakes are timing mistakes.

The two dates everyone mixes up

Open Enrollment is not the only window, and it is not for everything.

October 15 through December 7 is Medicare Open Enrollment, when anyone with Medicare can join, drop or switch a Medicare Advantage plan or a drug plan. Changes take effect January 1, and the plan has to receive your request by December 7.

It is the window most people know about. It is also not the window most people actually need.

• Open Enrollment, October 15 to December 7: change Advantage plans or drug plans, or move between Original Medicare and Advantage. Effective January 1.
• Medicare Advantage Open Enrollment, January 1 to March 31: only if you are already in an Advantage plan, and only one change. You can switch Advantage plans or drop back to Original Medicare and add a drug plan.
• During that January window you cannot move from Original Medicare into an Advantage plan, and you cannot switch drug plans if you are on Original Medicare.
• General Enrollment Period, January 1 to March 31: for people who missed their first window entirely. Coverage starts the first of the month after you sign up.

The most expensive trap on this page

Eight months for Part B. Two months for your drug plan.

The eight months for Part B is widely known. The two months for a drug plan is not. People use their eight months, feel like they handled it, and pick up a lifetime drug penalty on the way out.

• Part B after employer coverage ends: 8 months, beginning the month after the employment or the coverage ends, whichever happens first.
• Medicare Advantage or Part D after that same coverage ends: 2 full months. That is the one that catches people.
• COBRA does not extend either window. The clock runs whether or not you elect it.
• Going more than 63 days without creditable drug coverage is what triggers the Part D penalty.

Special Enrollment Periods

Life changes can open a window outside the calendar.

You do not always have to wait for the fall. A number of situations open a Special Enrollment Period, most of them running two full months after the month the change happens. If any of these describe you, call us before you assume you are stuck.

• You moved, and your plan is not available where you live now, or new plans are.
• You lost Medicaid eligibility. This one gives you 3 full months from the date you lost it or were notified, whichever is later.
• You moved into, live in, or moved out of a nursing home or long-term care facility.
• Your employer or union coverage ended, or you lost creditable drug coverage.
• Your plan left Medicare, or Medicare ended its contract with your plan.
• A plan near you holds Medicare's top quality rating of five stars. If one does, you can move into it once between December 8 and the following November 30.
• You were released from incarceration, or you moved back to the United States.
• You qualify for Extra Help or Medicaid. That allows a change once per calendar month.

One time only, and it never comes back

Medicare Supplement open enrollment does not repeat.

One six-month window, starting the first month you have Part B and are 65 or older. This is not the fall Open Enrollment period and it does not come around again. Assuming otherwise is how people lose a protection they cannot get back.

• Inside the window a company cannot refuse you, cannot use your health history to decide, and cannot charge you more for pre-existing conditions.
• After it closes there is no federal guarantee that anyone will sell you a policy, and if they do it may cost more.
• Guaranteed issue rights exist in certain situations after the window, including losing coverage through no fault of your own.
• You may have additional rights under Colorado law. Check with the Colorado Division of Insurance, or ask us and we will look with you.
• Supplements are standardized differently in Massachusetts, Minnesota and Wisconsin.

What arrives in the mail, and when

When to expect your card.

Already receiving Social Security at 65? You are enrolled automatically, and the card arrives about three months before coverage starts. Not claiming yet? Nothing arrives on its own. You have to apply.

• Enrolled automatically: welcome package roughly 3 months before coverage begins.
• Applying yourself: nothing comes automatically. You apply through Social Security, then the card follows.
• Enrolling due to disability: about 2 weeks after you sign up.
• If you join a Medicare Advantage plan, you will use that plan's card for care, not your red, white and blue card. Keep the Medicare card somewhere safe anyway.

Working past 65

The size of your employer changes the answer.

At 20 or more employees you can usually delay Part B while you are covered, with no penalty later. Under 20 and your job coverage might not pay properly without both Part A and Part B. That turns it from a penalty question into a coverage gap.

• 20 or more employees: delaying Part B is usually safe while the coverage lasts.
• Fewer than 20 employees: the group plan may not pay correctly without Part A and Part B.
• Health Savings Accounts: enrolling in Medicare, including premium-free Part A, ends your ability to contribute. Because Part A can be granted retroactively up to six months when you apply late, the conservative move is to stop contributions six months before you apply.