Sign Up on Time: Medicare Windows and Penalties

The story: Ruth and the COBRA trap

Ruth looks at a calendar and learns that a COBRA plan does not make it safe to wait on Medicare.

1. Narrator: Ruth left a clinic job last year and kept the work health plan through COBRA. Ruth’s Medicare birthday is coming up.
2. Ruth: I have COBRA, so I can wait on Medicare, right? A friend waited while still working.
3. Narrator: Not quite. COBRA is not the same as a plan from a job you have now. It doesn’t let Ruth wait on Part B safely.
4. Narrator: If Ruth misses the first window, Ruth could wait months for coverage and pay a higher Part B premium for life.
5. Ruth: Then I’ll sign up in my first window and put the dates on my calendar.
6. Narrator: Mark your Medicare window now. COBRA and VA care don’t count as job coverage.

What you’ll learn

1. Your first window

   Your first chance to sign up is called your Initial Enrollment Period. It opens a few months before the month you turn 65, includes that month, and closes a few months after. Medicare.gov shows your exact dates.

2. Automatic, or not

   If you already get Social Security checks when you reach Medicare age, you are signed up for Parts A and B automatically. Your card comes in the mail. If you don’t get checks yet, you need to sign up yourself.

3. Still working? Check the employer’s size

   You may be able to wait on Part B with no penalty if you have health coverage from a job you or your spouse have now, at a large enough employer. Keep proof of that coverage. At a small employer, Medicare usually pays first, so waiting on Part B can leave big gaps.

4. Traps and penalties

   COBRA, retiree health plans and VA care don’t count as job coverage for waiting on Part B. Signing up late can add a penalty to your Part B or Part D premium, often for life. Drug coverage as good as Medicare’s (creditable coverage) avoids the Part D penalty. TRICARE For Life requires Part B.

Key words

Initial Enrollment Period

your first sign-up window

creditable coverage

drug coverage as good as Medicare’s

late enrollment penalty

an add-on to your premium, often for life

primary payer

the plan that pays first

Common questions

I missed my window. What now?

You can still sign up in the general sign-up window each year. A penalty may apply. A free SHIP counselor can check whether a special window fits your situation. Find one at SHIPhelp.org.

I’m a veteran with VA care. Do I need Part B?

VA care doesn’t count as job coverage, and it mostly covers care from the VA. Many veterans sign up for Part B on time to keep their choices open. A lesson on veterans’ health coverage is coming.

Remember this

Mark your Medicare window now. COBRA and VA care don’t count as job coverage.

Try it: Put your Medicare window on the calendar

1. Find your Medicare window dates at Medicare.gov or SSA.gov.
2. Write the first and last day of the window on your calendar.
3. Still working? Ask the benefits office how its plan works with Medicare.

Put your sign-up window on your calendar.

Live facts

Numbers that change over time, with when they were last checked and where they come from.

• Medicare starts at

  65

  The age most people become eligible for Medicare

  As of February 8, 2026

  Source: Medicare.gov(opens in a new tab)

• Medicare Part B standard premium

  $202.90a month

  What most people pay each month for Part B; higher incomes pay more

  As of 2026

  Source: Medicare.gov(opens in a new tab)

• When you can sign up, and the employer-size rule

  Source: Medicare.gov(opens in a new tab)

• Late enrollment penalties

  Source: Medicare.gov(opens in a new tab)

• Free, unbiased Medicare help (SHIP)

  Source: SHIPhelp.org(opens in a new tab)