Medicare coverage should fit the way you live—your doctors, prescriptions, healthcare needs, and budget. As you prepare for 2027, taking time to review your coverage can help you understand what is changing and whether your current plan still meets your needs.

The Medicare Annual Enrollment Period runs from October 15 through December 7, 2026. Changes made during this period generally take effect January 1, 2027. This enrollment window applies to Medicare Advantage and Medicare prescription drug plans.

Whether you live in Oak Creek, the Milwaukee area, or elsewhere in Wisconsin, here are the dates and questions to keep in mind.

Start With Your Annual Notice of Change

If you currently have a Medicare Advantage plan or a Medicare Part D prescription drug plan, look for your Annual Notice of Change, often called an ANOC. Your plan sends this notice in September to explain changes taking effect in January. Check your mail and any electronic delivery options you use.

Read the notice even if you have been happy with your coverage. Pay particular attention to:

• Monthly premiums and deductibles.
• Copayments and coinsurance.
• Changes to prescription drug coverage.
• Changes to benefits or plan availability.

Also verify your doctors, hospitals, and pharmacies for the upcoming year. Keep a list of questions so you can address them during your coverage review.

October 1: Begin Reviewing Your Options

October is a good time to gather your plan documents and prepare for a conversation about next year’s coverage.

Watch for Health Insurance Solutions’ annual email or mailing, and visit www.wihis.net for meeting information and registration details.

You do not need to decide immediately. Begin by identifying what matters most to you: keeping a particular doctor, managing prescription costs, accessing care when traveling, or understanding what you may pay throughout the year.

October 15–December 7: Compare and Make Eligible Changes

During Medicare Annual Enrollment, you can generally:

• Join, switch, or drop a Medicare Advantage plan.
• Join, switch, or drop a Medicare Part D prescription drug plan.
• Move between Original Medicare and Medicare Advantage.

Your options depend on your eligibility and the plans available where you live. If you are considering returning to Original Medicare, review prescription drug coverage and Medicare Supplement eligibility before making a change.

Look Beyond the Monthly Premium

A premium is only one part of the decision. Consider how you expect to use your coverage.

For example, someone who sees specialists regularly may prioritize provider access and visit costs. Someone who takes several medications may focus on the drug list, pharmacy network, and prescription expenses.

Bring these items to your review:

• Your current insurance information.
• Your medication names, dosages, and preferred pharmacy.
• Your doctors and preferred hospitals.
• Any notices about coverage changes.
• Questions about upcoming care or travel.

Having this information ready makes the discussion more useful and personal.

December 7: The Annual Enrollment Deadline

December 7, 2026, is the last day of this Annual Enrollment Period to make changes for coverage beginning January 1, 2027.

Schedule your review early enough to ask questions and complete any necessary enrollment steps. If your current coverage continues to meet your needs, a review may confirm that keeping it is appropriate.

Can You Change Medicare Coverage Outside Annual Enrollment?

Sometimes. A Special Enrollment Period may allow changes outside the fall enrollment window when a qualifying event occurs.

Examples include moving outside your plan’s service area, losing certain coverage, a plan ending coverage in your area, or changes involving Medicaid or Extra Help. Specific deadlines and permitted changes vary by situation.

New to Medicare or Retiring?

People becoming eligible for Medicare generally have an Initial Enrollment Period, which is separate from Annual Enrollment.

If you are retiring or losing insurance based on current employment, you may have special enrollment rights. The timing for enrolling in Medicare Part B can differ from the timing for joining a Medicare Advantage or prescription drug plan. Review both before employer coverage ends.

Moving, Changing Medicaid Status, or Considering Special Needs Coverage?

Contact an agent when your circumstances change. Moving across a county line does not automatically create an enrollment opportunity; your new address and available coverage matter.

Certain chronic conditions or eligibility for both Medicare and Medicaid may open access to specific Special Needs Plans and associated enrollment opportunities. Eligibility must be confirmed.

What About Wisconsin SeniorCare?

If you gain Wisconsin SeniorCare prescription coverage, ask how it affects your current coverage and enrollment options. Participation in a qualifying State Pharmaceutical Assistance Program may provide a Special Enrollment Period, subject to Medicare’s rules.

Does Annual Enrollment Apply to Medicare Supplements?

Medicare Supplement insurance, also called Medigap, follows different rules from Medicare Advantage and Part D. The October 15–December 7 enrollment period does not create a general guaranteed right to buy or switch a Medigap policy.

You can request a review throughout the year, especially after receiving a premium increase. However, switching may require medical underwriting unless you have applicable enrollment protections or guaranteed issue rights. Premium change dates depend on your policy and insurance company.

Get Personal Help With Your Medicare Review

You deserve clear explanations and time to understand your choices.

Health Insurance Solutions is an independent insurance agency based in Oak Creek, serving consumers throughout Wisconsin. Our team can help you review available options and discuss whether a change makes sense for your circumstances, with appointments by phone, virtually, or in person.

Call 414-766-9700 or visit www.wihis.net to schedule your Medicare coverage review.

This article provides general education. Enrollment eligibility, coverage, costs, and effective dates depend on your circumstances and the applicable plan rules.