I’m turning 65 in Illinois and still working. Do I need to sign up for Medicare right away?
Answered by 7 licensed agents
If you are still working at 65 and covered by an employer group health plan through your or your spouse’s current employment, you may be able to delay Medicare Part B without a late-enrollment penalty.
The first thing to check is the employer size.
If the employer has 20 or more employees, the employer plan generally continues to pay first, and many people can delay Part B while that coverage remains active.
If the employer has fewer than 20 employees, Medicare generally becomes primary at 65. In that situation, delaying Parts A and B can create unpaid claims because the employer plan may expect Medicare to pay first.
Also ask whether you contribute to an HSA. Once Medicare begins, you can no longer contribute to an HSA, so that needs to be planned before enrolling in Part A or Part B.
COBRA, retiree coverage and VA benefits are also different from coverage based on current employment and should not automatically be treated as reasons to delay Part B.
So about six months before you turn 65, have the employer benefits reviewed. Confirm the employer size, whether the coverage is based on current employment, how it works with Medicare, and whether you are contributing to an HSA.
Then you can decide whether enrolling at 65 or delaying Medicare is the better path for your situation.
Answered by Jeremy Harkins on September 21, 2026
Broker Licensed in TN, AR, CA & 5 other states
If you’re turning 65 in Illinois and still working, the first question I would ask is not simply, “Are you still working?” It is, “What kind of health insurance do you have through work, and how large is the employer?”
If you have health coverage through your or your spouse’s current employment and the employer has 20 or more employees, you may be able to delay Medicare Part B without a late-enrollment penalty. When that employer coverage eventually ends, you generally have a Special Enrollment Period to enroll in Medicare.
If the employer has fewer than 20 employees, the situation can be very different. Medicare generally becomes the primary payer at age 65, which means delaying Medicare could leave you with a significant gap in coverage.
There are a few other things I would check before making the decision:
Is the employer coverage based on current employment, rather than COBRA or retiree coverage?
Is the prescription coverage considered creditable for Medicare Part D?
Are you contributing to a Health Savings Account (HSA)?
What does the employer plan cost compared with Medicare?
Are you covering a spouse or other dependents who still need the employer plan?
The HSA question is especially important. Once you are enrolled in Medicare, you can no longer contribute to an HSA. If you delay Medicare past age 65, Medicare Part A can also become retroactive when you eventually enroll, so the timing needs to be planned carefully.
That is why I don’t automatically tell someone turning 65 to either enroll in Medicare or stay on the employer plan.
We compare the two before making the decision.
The goal is to determine which coverage gives you the right combination of doctors, prescriptions, benefits, costs, and flexibility—and to make sure you don’t accidentally create a Medicare penalty or coverage gap.
Turning 65 is a Medicare milestone. It doesn’t automatically mean you have to leave your employer coverage.
Answered by Edward Givens on September 12, 2026
Broker Licensed in AZ, CA, CO & 13 other states
Answered by Madison Schoenherr on September 10, 2026
Broker Licensed in IL, IN & MI
Answered by Vincent Orender on September 11, 2026
Broker Licensed in PA, AL, AZ & 10 other states
Answered by Jorge Collado on September 10, 2026
Broker Licensed in FL, AL, AR & 42 other states
Answered by Gisele Salas on October 6, 2026
Agent Licensed in FL
Answered by Ruth Neuenschwander on October 5, 2026
Broker Licensed in OH, FL, IN, KY & MI
Tags: Advice for Seniors The Medicare System Turning 65
Agents: Share Your Expertise
Have insights or experiences related to this topic? Help others by sharing your knowledge and answering this question.
Seniors: Ask a Question of Your Own
Questions are generally answered within 1 to 3 business days. Receive valuable perspectives from multiple licensed agents and brokers.
Ask a Question