Medicare Moments | Learn your Medicare enrollment options if you are over 65, retiring with serious health issues

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, Calif.

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. (To understand Medicare Part D and the changes read chapter 5 of Toni's Medicare Survival Guide Advanced edition.)

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 prescription drug plan. If your drugs are not on your Part D 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" what it offers. Those receiving Medicare Part B for the first time need to understand the value of the Medigap(also known as Medicare Supplement) 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 6-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 6-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 not just your primary care doctor which Medicare Advantage HMO or PPO plans they accept.

For answers to your Medicare questions, call the Toni Says Medicare team at 832-519-8664 or email your question to [email protected]. Visit www.tonisays.com to sign up for the Toni Says newsletter and download at no cost the new 2026 Medicare Roadmap workbook.