What are Medicare’s enrollment rules for self-employed people?

Dear Toni: I am self-employed with an individual health plan and confused about enrolling in Medicare when I turn 65 in July. I cannot find the answer to my situation in the “Medicare &You” handbook.

A business associate who is also self-employed delayed his Part B because he is under his wife’s company benefits. He is sure that I can delay enrolling in Medicare, too, since I am covered by a health insurance plan.

Can you please explain the difference between my situation and my friend’s? I do not want to make a Medicare mistake. — Greg, Corpus Christi, Texas

Dear Greg: Recently, I consulted a 66-year-old man who was also self-employed and was given wrong information about delaying his Medicare Part B. He was surprised to find out that Medicare does not recognize individual plans as “true” employer benefits to delay Part B.

Qualifying group benefits are defined in the “Medicare &You” handbook as companies with 20 or more employees.

The pertinent information is found on Page 20 of the 2025 Medicare &You handbook under “Health Insurance Marketplace”: “You should sign up for Medicare when you’re first eligible to avoid the risk of a delay in Medicare coverage and the possibility of a Medicare late enrollment penalty.”

The self-employed 66-year-old will be assessed a monthly 20 percent penalty — 10 percent for each year past age 65 that he failed to enroll — for not signing up for Part B during his initial enrollment period.

Greg, I recommend you enroll in Medicare during your initial enrollment period, which starts three months before you turn 65, so that your Medicare coverage begins July 1. You currently have an individual health insurance plan, not true group health insurance, which can lead to a Medicare penalty if you do not enroll at the right time. Go to ssa.gov to sign up.

Many Americans believe that Medicare enrollment is automatic when turning 65. This is correct only if you are already receiving your Social Security check at that time.

Your business associate, who is covered under his working spouse’s true employer benefits, can delay enrolling in Medicare. But he must follow Medicare’s enrollment rules upon losing those benefits, which will open an eight-month special enrollment period in which to apply.

Toni King is an author and columnist on Medicare and health insurance issues. If you have a Medicare question, email info@tonisays.com or call 832-519-8664.