Toni Says: Medicare enrollment options if you are over 65 and have preexisting health conditions
Hello Toni,
I’m retiring January 1, 2027, and beginning to research what is the right Medicare option for me and my wife, Jennifer, who is receiving breast cancer treatment. Jennifer’s cancer drugs are expensive, and I am concerned about the Medicare Part D out of pocket. I am a diabetic, use a flex pen and take high blood pressure medications. Most of my prescriptions are generic, except for the diabetic flex pen.
Our Medicare Part B will begin January 1, as my company benefits will end December 31 of this year. I will be 70 when I retire, and Jennifer is turning 65 in November and will have January 1 as her Medicare start date.
Please explain what our options are so that I am sure that Jennifer and I enroll in Medicare the correct way. I’m looking forward to what you have to say about this stressful Medicare subject. Thanks, Toni.
—David from San Diego
Great question, David:
When the Toni Says Medicare team meets with clients during a Medicare consultation, we emphasize that Medicare is not cookie cutter … one size does not fit all! Everyone’s health, finances and prescriptions are different. David, you and Jennifer’s health care needs, as well as the prescription drugs you both are taking currently, should be considered when finalizing your Medicare choices.
The cornerstone of Medicare planning at the Toni Says offices is discussing Medicare Part D prescription drug planning. David, it is imperative to search for the most cost-effective Medicare Part D prescription drug plan that covers all the prescriptions that you and Jennifer take.
Many people on Medicare simply don’t practice proper Medicare Part D planning. They are more concerned about their doctors and fail to notice whether their prescriptions are covered under their new Medicare Part D or Medicare Advantage prescription drug plan.
Every Medicare Part D plan has a prescription drug formulary, whether it is a stand-alone Part D plan or Medicare Advantage (Part C) with a prescription drug plan. If your drugs are not on your plan’s formulary, then you will pay 100% out of your pocket.
The 2027 Medicare Part D plans will be released this fall at the medicare.gov website on October 1 for Medicare’s Open Enrollment Period, which runs October 15 through December 7 for a January 1 effective date. David, because you are retiring January 1, I recommend that around October 1 you and Jennifer begin researching which Medicare Part D plan covers all your prescriptions with the lowest prescription drug premium and cost.
Now let me explain Medicare Part B, because it is like gold with what it offers. Those receiving Medicare Part B for the first time need to understand the value of the Medicare Supplement (also known as Medigap) Open Enrollment Period. Page 77 of the 2026 Medicare & You Handbook discusses when to buy a Medigap/Medicare Supplement policy. It states “The best time to buy a Medigap/Medicare Supplement policy is during your Medigap Open Enrollment Period. This 6-month period begins the first month you have Medicare Part B (Medical Insurance), and you’re 65 or older.”
During this six-month window you can enroll in any Medigap/Medicare Supplement plan without having to answer any health questions and you cannot be denied coverage. After the six-month window, then medical underwriting takes place, and those with existing health problems may not qualify for a Medigap/Medicare Supplement Plan.
Many new Medicare beneficiaries explore a Medicare Advantage plan (Part C), which can be a good option. With the health conditions that you and Jennifer have, please discuss with all your doctors which Medicare Advantage HMO or PPO plans they accept.
Remember, with Medicare, what you don't know WILL hurt you! Chapter 5 of Toni’s Medicare Survival Guide Advanced edition discusses Medicare Part D in detail. Toni’s new “Confused About Medicare” video series and Medicare Roadmap are available at www.tonisays.com.
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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
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