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I Have to Enroll in Medicare When I Turn 65, Right?

It’s the question/statement I hear most often.  And the definitive answer is Maybe.

Turning 65 is not the only time you can sign up for Medicare. There are actually four Enrollment Periods for entering Medicare. 

The two most common are:

  • Initial Enrollment Period – 7 months around your 65th birthday

  • Special Enrollment Period – When your employer insurance ends

You must (if you want to avoid a penalty) enroll in Medicare at age 65 if:

  • You are drawing Social Security retirement benefits

  • You are on an individual health insurance policy (from “the exchange”)

  • You are on COBRA or

  • Your employer has less than 20 employees on its group health insurance plan. This is the Gotcha!

For Medicare eligible individuals who are still working and have employer group health insurance with 20 or more employees, it is most often advisable to stick with the employer plan and NOT sign up for Medicare.  A definite exception is someone with a High Deductible Health Plan and a chronic condition that leads to meeting that deductible each year.


Contributor: Mj Heins, learn more at:

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