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Dear Toni:

I have decided to retire in October when I turn 65 and will need to enroll in Medicare Parts A and B. My husband, Paul, is 76 and was enrolled in Medicare Parts A and B on March 1, 2011, when he qualified for Social Security disability due to a Parkinson’s issue. He has remained on my company benefits due to his health.

Toni, I need your guidance with retiring, leaving employer benefits and making sure that Paul and I enroll in the Medicare Supplement that fits our medical needs. Looking forward to your advice. Thank you, Toni.

—Elizabeth from Conroe, Texas

Hello Elizabeth:

Medicare has special rules for employees still working, with or without spouses, who are covered by the employer group health insurance and need to enroll into Medicare Part B.

Enrolling in Medicare Part B the right way is crucial because, if done the wrong way when leaving employer benefits, it can cause you or Paul not to qualify medically for the Medicare Supplement you desire.

There is a Medicare Supplement rule that eliminates the need for Paul to answer underwriting questions since he is leaving your employer benefits and applying for a Medicare Supplement. Specifically, due to his Parkinson’s, he will not have to answer medical underwriting questions to qualify for one.

That’s because Paul qualifies for the 63-day guaranteed issue period rule for Medigap protection and can apply for a Medicare Supplement/Medigap plan without medical underwriting. All he will need to qualify is to provide the employer benefit termination letter with his name included to prove to the Medicare Supplement plan that he is in a 63-day guaranteed issue period. When he applies for the Medicare Supplement he will only be able to apply for Medicare Supplements Plan F or C because his Part A began prior to Jan.1, 2020. Medicare Supplement plan G is not an option. Please view the information below regarding guaranteed issue rules.

With guaranteed issue, an insurance company must:

—Sell you a Medicare Supplement/Medigap policy. You have the right to buy Medicare Supplement/Medigap plan A, B, C, F, K or L that’s sold in your state by any insurance company. Paul is not eligible for Plan G with guaranteed issue plans since his Medicare Part A began prior to Jan. 1, 2020, so Medicare Plan F would be his first option, with Plan C following. Medicare beneficiaries whose Medicare Part A began after Jan. 1, 2020, are eligible for Plan G, not Plan F or C, for a guaranteed issue plan. Remember that you have a 63-day window to apply without having to answer underwriting questions and must provide an employer insurance termination notice with the guaranteed issue client’s name included.

—Cover all your pre-existing health conditions.

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

Elizabeth, since you are turning 65, you are in your Medicare Supplement/Medigap Open Enrollment Period, and as the 2026 Medicare & You handbook states on page 77, “The best time to purchase a Medicare Supplement/Medigap policy is during your Medigap Open Enrollment Period. This 6-month period begins on the first day of the month you have Medicare Part B (Medical Insurance) and you’re 65 or older.”

Because you are turning 65 in October and retiring, this process will be easy. Visit the Social Security website at www.ssa.gov/medicare/sign-up and enroll online. There is a seven-month window to enroll in Medicare that includes three months before the month you turn 65, the month you turn 65, and three months after turning 65. Elizabeth, since it will be October when you will enroll in Medicare, then your Medicare Part A will begin Oct. 1 and your Part B will begin Nov. 1.

Remember, with Medicare, what you don’t know WILL hurt you.

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Toni King is an author and columnist on Medicare, Social Security and long-term care issues. She has spent nearly 30 years as a top sales leader in the field. If you have a Medicare question, email info@tonisays.com or call 832-519-8664. Sign up for the Toni Says newsletter at www.tonisays.com to keep up to date on Medicare changes.

©2026 Toni King. Distributed by Tribune Content Agency, LLC.

Copyright 2026 Toni King, Distributed by Counterpoint Media