Dear Toni: I am retiring in February when I turn 65 and will need to enroll in Medicare Parts A and B with a Medicare Supplement and a Part D prescription drug plan.

My husband, James, is 72 and has heart issues, so he enrolled in Medicare A and B when he turned 65 and remained on my company benefits to have his heart surgery. He is taking Eliquis for blood clots.

The manager at James’ cardiologist’s office expressed concern over my husband’s insurance changes. Since their office accepts few Medicare Advantage plans, she suggested that Medicare with a Medicare Supplement would be the right choice for James.

We need your help. Please explain what I need to do to get Medicare Supplement coverage for both me and James. Thanks, Toni. — Paulina from Mobile, Ala.

Hello Paulina: Americans do not realize how confusing it is to enroll in Medicare when retiring and leaving employer benefits. When you enroll in Part B the wrong way, it can cause you to not qualify for the Medicare benefits you want, whether it’s a Medicare Supplement with a stand-alone Part D prescription drug plan or a Medicare Advantage Part D plan.

Medicare provides special rules for employees or spouses who are “still working” with “true” company benefits and are covered by the employer group health insurance.

Paulina, you are in your Medigap Open Enrollment Period and on page 77 of the 2025 Medicare & You handbook it states, “The best time to buy a Medigap policy is during your 6-month Medigap Open Enrollment Period. During that time, you can buy any Medigap policy sold in your state, even if you have health problems. This period automatically starts the first month you have Medicare Part B (Medical Insurance) and are 65 or older. After this 6-month period, you may not be able to buy a Medigap policy due to health issues. If you’re able to buy one, it may cost more.”

Paulina, because you’re in your Open Enrollment Period, you can have your Medicare Supplement Plan G with a Part D prescription drug plan begin on Feb. 1 when your Medicare Part B starts without answering one health question.

James’ Medicare situation is different because he enrolled in Medicare Part B when he turned 65 over 7 years ago. Now he must answer underwriting questions to qualify for a Medicare Supplement.

That’s why enrolling in Part B the correct way and at the right time, when an enrollee or spouse is “still working” full-time with true company benefits, is important. You also want to be accepted by a Medicare Supplement/Medigap plan due to your age and medical issues.

There is good news, Paulina. James’ saving grace for bad underwriting is that James and you are leaving your employers benefits. He will receive a 63-day “guaranteed issue” period to apply for a Medicare Supplement/Medigap plan. Keep the employer benefit termination letter to show the Medicare Supplement insurance company that James is in a Guaranteed Issue Period.

According to your rights under the Guaranteed Issue Period an insurance company must:

— Sell you a Medigap/Medicare Supplement policy. You have the right to buy a Medigap/Medicare Supplement plan A, B, C, D, F, G, K or L that’s sold in your state by any insurance company. (Plans C & F are available to those who were eligible for Medicare before January 1, 2020. Plans D and G are eligible for those new to Medicare on or after January 1, 2020.)
— Cover all your pre-existing health conditions.

— Cannot charge you more for a Medigap/Medicare Supplement policy, regardless of past or present health problems.

Most people don’t realize the value of delaying enrollment in Medicare Part B until they are in James’ situation. They apply for a Medicare Supplement learning they may not qualify because they are no longer in their Medicare (supplement) Open Enrollment period. James can only qualify for Medicare Supplement Plan F. He will not qualify for Plan G because he would not pass underwriting to qualify health-wise.

Readers, it’s important to research your Medicare options when turning 65, even if you are covered by your own or your spouse’s employer benefits — because with Medicare, what you don’t know will hurt you.

Toni King is an author and columnist on Medicare and health insurance issues. She has spent nearly 30 years as a top sales leader in the field. For a Medicare checkup, call the Toni Says call center at 832-519-8664 or email info@tonisays.com regarding your Medicare plans and options. Toni Says Medicare Survival Guide Advanced edition is available at www.tonisays.com.