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Turning 65? When to enroll in Medicare

James AsherBy James Asher, licensed Medicare agent · Updated September 29, 2026 · 2 minute read

Enroll in the three months before your 65th birthday month. Your first Medicare window, the Initial Enrollment Period, runs seven months: three months before your birthday month, the month itself, and three months after. Sign up in the first three and your coverage starts on the first day of your birthday month, with no gap.

Your seven-month window

Say your birthday is in March. Your window opens December 1 and closes June 30. Enroll in December, January or February and Parts A and B begin March 1. Enroll in March or later and coverage starts the first of the month after you sign up, which leaves a gap.

One wrinkle: if your birthday is on the first of the month, everything shifts one month earlier. A March 1 birthday means coverage can start February 1.

What to do and where

If you already receive Social Security, Medicare enrolls you automatically. Your red, white and blue card arrives about three months before your birthday. If you are not on Social Security yet, you apply at ssa.gov or by phone. It takes about ten minutes online.

Parts A and B come from the government. A drug plan, a Medicare Supplement or a Medicare Advantage plan comes from a private insurance company, and that is the part I help with. Those choices have their own deadlines, and they line up with the same window.

If you are still working

If you have health coverage through a job with 20 or more employees, you can delay Part B without a penalty. Most people in that spot take Part A, which is free, and wait on Part B. Read the answer on working past 65 before you decide, because the rules differ for smaller employers and for retiree coverage.

What happens if you miss it

Missing the window without employer coverage means a late penalty on Part B that lasts as long as you have Medicare, and a wait until the next General Enrollment Period, January 1 to March 31. The penalty is avoidable. Put the open date on your calendar and call me the month before.

Use the date finder on the home page to see your exact dates, then request a plan check. I confirm your dates and line up your plan so it starts the same day your Medicare does.

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