Healthcare is consistently one of the largest expenses in retirement, yet the system designed to pay for it is famous for its complexity. If you are already enrolled in Medicare and staring at a stack of insurance marketing mail, the rules, deadlines, and potential penalties can feel overwhelming.

You do not need to become a Medicare expert. However, you do need to evaluate whether your current coverage is still the best option for your health and your wealth.

To help simplify this process, we have provided a decision flowchart you can download and review alongside this guide:

Should I Change My Medicare Coverage During Open Enrollment – 2026

If you are looking to optimize your existing coverage, here is exactly how to navigate the 2026 Open Enrollment season.

Quick Refresher: Your Two Paths

The number one mistake people make during Open Enrollment is confusing Medicare Advantage with Medigap (Medicare Supplement). Before you change plans, you must understand the core trade-off between the two primary paths of Medicare coverage.

• Path One: Original Medicare + Medigap + Part D. You use Original Medicare (Parts A and B) as your primary insurance, buy a Medigap policy to cover the 20% Original Medicare does not pay, and purchase a standalone Part D plan for prescriptions. This path typically offers maximum flexibility to see any doctor who accepts Medicare nationwide without needing referrals, but it comes with higher, predictable monthly premiums.
• Path Two: Medicare Advantage (Part C). You bundle your coverage into a single private plan that usually includes prescription drug coverage and extra perks like basic dental or vision. This path often features low (or zero) monthly premiums, but it requires you to use the plan’s specific, localized network of doctors and hospitals, and you will pay copays as you receive care up to an annual out-of-pocket limit.

The Medicare Open Enrollment Period (Oct 15 – Dec 7)

Health insurance plans change their networks, formularies, and pricing every single year. Even if your health has not changed at all, the plan you loved might not be the most cost-effective option for the upcoming year.

From October 15 through December 7 every year, the Medicare Open Enrollment period allows you to completely overhaul your healthcare coverage. Any changes you make during this window will take effect on January 1, 2027.

During this window, you are allowed to:

• Switch paths entirely: You can move from Original Medicare to a Medicare Advantage plan, or you can drop your Advantage plan and return to Original Medicare.
• Switch Advantage plans: If you are already in a Medicare Advantage plan, you can switch to an entirely different Advantage plan.
• Adjust drug coverage: If you have a standalone Part D prescription drug plan, you can drop your current plan, switch to a different one, or add one for the first time.

The Annual Review: Why You Need to Look at Your Plan

Do not let your plan automatically renew without checking the details. Before Open Enrollment ends, ask yourself:

• Have your out-of-pocket costs changed? Look beyond just the monthly premium. Compare deductibles, copays, and the plan’s out-of-pocket maximum to see if your total exposure is increasing.
• Has your drug formulary shifted? A medication that cost you $15 last year might be moved to a higher “tier,” significantly increasing your copay. Always verify that your specific prescriptions are still covered affordably.
• Are your doctors still in-network? Provider networks change annually. Ensure your preferred doctors, specialists, and local hospitals are still actively participating in the plan’s network.
• Are you paying for “extras” you don’t use? Many Medicare Advantage plans heavily market extra benefits like gym memberships. If you are paying a premium for these but not utilizing them, a leaner plan might serve you better.

The Medicare Advantage “Second Chance” Window

If you miss the December 7 deadline and you are currently enrolled in a Medicare Advantage plan, you get a second chance.

Between January 1 and March 31, there is a specific Medicare Advantage Open Enrollment Period. During these three months, you can switch to a new Advantage plan or return to Original Medicare (and pick up a Part D plan).

Keep in mind, this specific window is only available to those currently on an Advantage plan; it does not apply to those on Original Medicare who simply want to change their Part D drug coverage.

The Medigap Reality Check (Beware the Underwriting Trap)

It is a very common misconception that you can easily switch Medigap plans during the fall Open Enrollment window. Medigap policies operate under entirely different rules.

You get a one-time, six-month Medigap Open Enrollment Period that begins the month you turn 65 and are enrolled in Part B. During this six-month window, you have a “guaranteed issue” right—meaning an insurance company cannot refuse to sell you a policy or charge you more due to pre-existing health conditions.

While you can technically apply to change your Medigap policy at any time during the year, doing so outside of that initial guaranteed issue window usually means you are subject to medical underwriting.

This means an insurance company can look closely at your current health history and legally deny you coverage or charge you significantly higher premiums based on pre-existing conditions. If your strategy is to drop a Medicare Advantage plan and return to Original Medicare with a Medigap policy, you must ensure you can actually pass underwriting and secure the Medigap policy before you drop your Advantage coverage.

Understanding Your Costs for 2026: Premiums and the IRMAA Cliff

Medicare is not free, and for high-net-worth retirees, it can be surprisingly expensive due to the Income-Related Monthly Adjustment Amount (IRMAA).

For 2026, the standard Part B premium is $202.90 per month. However, the government applies significant surcharges to both Part B and Part D premiums for higher-income beneficiaries.

IRMAA is calculated based on your Modified Adjusted Gross Income (MAGI) from your tax return two years prior. This means your 2026 Medicare premiums are dictated by the income you reported on your 2024 tax return. For 2026, these surcharges begin if your 2024 MAGI exceeded $109,000 for single filers or $218,000 for married couples filing jointly.

Because IRMAA operates on a strict “cliff” system, earning just one dollar over a threshold pushes you into the next surcharge tier for the entire year, resulting in hundreds or thousands of dollars in additional costs. Managing your taxable income in retirement—such as working proactively with a tax professional to map out Roth conversions or strategically plan the realization of large capital gains—is critical to preventing unnecessary spikes in your healthcare costs.

Putting It All Together

Navigating Medicare requires balancing your budget, your desire for doctor flexibility, and your specific medical needs. It is rarely a fun process, but systematically reviewing your choices is one of the highest-return activities you can do to protect your wealth in retirement.

Because we do not sell Medicare policies or take commissions from insurance companies, our focus at Suttle Crossland Wealth Advisors is entirely on how your healthcare decisions impact your broader financial plan. Take the time to review your options this fall. Download the decision guide linked above, check your current prescriptions against 2026 formularies, and ensure your healthcare coverage is working as hard as you did to earn it.