What You Should Review During Medicare's Annual Enrollment Period
Medicare's Annual Enrollment Period runs from October 15th through December 7th. Whatever you choose during those weeks takes effect January 1st and generally stays in place for the full year.
Most people let it pass and allow their coverage to renew on their own. The window exists because plans do not hold still. Premiums move, drug lists get rewritten, and physicians leave networks. Annual enrollment is the time of year in which you can review your coverage and make sure it still fits your situation.
What You Can Change
During Annual Enrollment you can move from Original Medicare to a Medicare Advantage plan, move from an Advantage plan back to Original Medicare, switch from one Advantage plan to another, or join, switch, or drop a standalone Part D prescription drug plan. You are allowed to change your mind more than once. The last request you submit before December 7th is the one that takes effect.
The window does not grant any special right to buy a Medicare Supplement policy. Medigap runs on its own rules, and that distinction matters a great deal for anyone thinking about leaving a Medicare Advantage plan.
Every Medicare Advantage and Part D plan is required to mail an Annual Notice of Change by September 30th. It sets this year's terms next to next year's. This includes the plan’s premium, deductible, copayments, covered drug list, provider network, and any supplemental benefits. It should arrive directly to your address on file.
If your plan is still offered in your area, you can be renewed into it automatically. However, keep in mind that the automatic renewal is not the same as unchanged coverage. You are renewed into whatever the plan looks like next year. Same plan name, same card, but possibly different terms.
What is Worth Checking
Start with prescriptions. Pull your current medication list and confirm each one still appears on next year's formulary and at what tier. A drug can remain covered while moving to a higher tier, which changes what you pay without changing whether you are covered. Plans can also add conditions such as prior authorization or step therapy, meaning you must try an alternative before the plan will pay for what you take now.
Pharmacy matters as well. Many drug plans designate preferred pharmacies where the identical prescription costs less, and that designation can shift from one year to the next.
Next item to consider is providers. If you are in a Medicare Advantage plan, confirm your physicians and your preferred hospital are in the network for the coming year. Networks are set annually. This step does not apply to Original Medicare, where any provider who accepts Medicare will see you.
For a Medicare Advantage plan you want to compare total cost of the plan rather than only considering the premium. That means the deductible, the copayments for the kind of care you actually use, and the annual out of pocket maximum, which is the ceiling on what the plan can require you to pay in a year. A plan with no monthly premium and a high maximum can cost considerably more than a plan with a modest premium in a year when something goes wrong. The premium is the number the advertising leads with, but it doesn’t show you the full cost associated with the plan when you take into account using your coverage.
Medicare's plan comparison tool at medicare.gov will do most of this work if you enter your medications and your pharmacy. It returns an estimated annual cost for each plan available where you live, this comparison can get you closer on determining whether a plan is the right fit for you.
Prescription coverage now works differently and the numbers reset each year
The Part D structure many people remember, with a coverage gap in the middle where costs jumped without warning, no longer exists. Drug coverage runs through a deductible phase, an initial coverage phase, and a cap. Once your out-of-pocket spending on covered drugs reaches the annual limit, you pay nothing further for covered drugs for the rest of the calendar year. That limit is $2,400 for 2027, which has increased from $2,100 in 2026.
Medicare also now requires every drug plan to offer a payment option that spreads your out-of-pocket drug costs across the calendar year in monthly installments instead of charging them at the pharmacy counter as they occur. It does not reduce what you owe, but being able to spread this amount into regular payments can make a large difference to someone who otherwise would be facing a substantial cost in January. Participation is elected rather than automatic, so anyone using it should review this process and make sure they have opted in.
Leaving Medicare Advantage for Original Medicare is not always reversible
You are permitted to drop a Medicare Advantage plan and return to Original Medicare during Annual Enrollment. Drug coverage is the easy part, since you can join a standalone Part D plan in the same window. The supplement is where people run into trouble.
Most people on Original Medicare carry a Medigap policy, because Original Medicare, on its own, has no annual limit on out-of-pocket costs. The guaranteed right to buy a Medigap policy regardless of your health history lasts six months, most commonly beginning when you are 65 and enrolled in Part B. Outside that window and a limited set of federally protected circumstances, most states permit insurers to review your medical history and either charge more or decline to issue a policy. So, before you drop your Medigap insurance, review your state regulations regarding re-enrolling in Medigap to see if it is your best option.
From January 1st through March 31st, a separate window applies only to people already enrolled in a Medicare Advantage plan. It permits one change. You are able to switch to a different Advantage plan or return to Original Medicare and pick up a Part D plan. It exists for someone who discovers in January that a new plan does not work, not as a second shopping season. It does not allow someone in Original Medicare to join an Advantage plan.
Higher income households pay a surcharge on top of the standard Part B and Part D premiums, calculated from the tax return filed two years earlier. That surcharge follows the person rather than the plan. Switching to a Medicare Advantage plan with drug coverage included does not remove it.
If your premium came in higher than expected for that reason, the remedy is to request an adjustment to Social Security based on a qualifying event, such as retirement, supported by documentation.
Making the Review Worth the Time
In most years, the review ends with a decision to keep what you have, which is a fine outcome when it is reached deliberately. The years it pays off are the ones where a medication changed, a diagnosis arrived, a physician left a network, or a plan restructured its cost sharing.
Set aside an hour once the Annual Notice of Change arrives. Have your medication list, your pharmacy, and the names of your doctors in front of you and review the changes to your plan and see if it still works for you.
Healthcare is one of the larger and less predictable line items in a retirement budget, and the coverage you carry interacts with the rest of your financial picture more than most people expect. Our team at Corbett Road Wealth Management works through these decisions alongside income planning, tax projections, and the timing of withdrawals, so a coverage choice made in November is not quietly working against a strategy built for the rest of the year. If you would like a second set of eyes on your Annual Notice of Change before December 7th, or you would like to discuss how any health insurance changes may impact your overall financial situation, reach out and we can walk through it together.
This post is intended for general informational purposes only and does not constitute legal, tax, or insurance advice. Plan availability, costs, and Medigap rules vary by state and are subject to change. Please confirm the details of your own coverage with your plan and consult a qualified advisor for guidance specific to your circumstances.
IMPORTANT DISCLOSURES
This post was created with the assistance of AI tools for research and drafting. It was reviewed, edited, and fact-checked by Camilla Carvalho before publication. Please verify any critical information.
These materials are provided for general information and educational purposes based upon publicly available information from sources believed to be reliable—we cannot assure the accuracy or completeness of these materials. The information in these materials does not constitute tax or legal advice and may change at any time and without notice. Please consult with a qualified tax professional, attorney, or Wealth Manager regarding your specific situation.
Spire Wealth Management, LLC is a Federally Registered Investment Advisory Firm. Securities offered through an affiliated company, Spire Securities, LLC., a Registered Broker/Dealer and member FINRA/SIPC.
