Medicare is one of the cornerstones of retirement planning. For most Americans turning 65, it becomes the primary source of health insurance—and for many, one of the most important factors in their overall financial security. But with new Medicare changes in 2026, retirees and pre-retirees need to prepare for possible increases in premiums, shifting benefits, and new rules that could impact their coverage and costs.
At Winthrop Partners, we believe that understanding these changes is critical for creating a retirement plan that keeps you both financially secure and confident in your healthcare.
Medicare in 2025: What Happened and Why It Matters
The 2025 Medicare Annual Enrollment Period (AEP) brought major shifts. The elimination of the prescription drug “donut hole” lowered out-of-pocket prescription costs from $8,000 to $2,000 per year. This was a welcome relief for retirees, but it created new financial challenges.
Insurance companies absorbed those costs by raising Medicare Advantage premiums, adjusting Part D drug coverage, and in some cases, exiting the Medicare marketplace altogether. Many beneficiaries were left scrambling to find new coverage, highlighting how quickly the landscape can change.
Key Medicare 2026 Changes to Watch
Looking ahead, the 2026 Medicare enrollment period is expected to bring further disruption. Here are the most important areas retirees should be aware of:
1. Rising Premiums and Reduced Benefits
- Many Medigap and Medicare Advantage plans are anticipating double-digit premium increases.
- Some states are adding “birthday rules,” which let enrollees switch to equal or lesser plans without underwriting. While consumer-friendly, this change may also lead carriers to adjust pricing strategies.
2. Higher Prescription Drug Costs
Despite reforms, Medicare prescription drug prices are expected to climb in 2026. This will affect both Part D standalone plans and Medicare Advantage plans that include drug coverage.
3. “One Big Beautiful Bill” Uncertainty
Beginning in 2026, automatic spending cuts of roughly $500 billion could reduce Medicare funding unless Congress intervenes. Potential impacts include:
- Lower provider reimbursement rates, which may reduce the number of doctors accepting Medicare.
- Loss of ancillary benefits like dental, vision, and hearing in Medicare Advantage plans.
4. Expanded HSA Contributions for Working Seniors
Starting January 1, 2026, seniors who are enrolled in Medicare Part A but still working with a high-deductible health plan will be able to continue contributing to Health Savings Accounts (HSAs)—a positive development for those who want more tax-advantaged flexibility.
5. Prior Authorization in Original Medicare
Traditionally, Original Medicare did not require prior authorization for services, a major advantage over many other plans. Pilot programs introducing prior authorization for certain procedures could change that in the future.
Steps to Prepare for Medicare 2026
Staying proactive is the best way to navigate the Medicare 2026 changes. Here’s what retirees should do now:
- Review Your Annual Notice of Change (ANOC)
Every September, Medicare enrollees receive an official notice detailing upcoming plan changes. Keep this document—it can even serve as proof for special enrollment rights if your plan is discontinued. - Compare Plans During the Annual Enrollment Period (Oct 15 – Dec 7)
Use resources like Medicare.gov or consult with an advisor to review whether your doctors, prescriptions, and costs align with your current plan. - Evaluate Lifestyle and Budget Fit
Don’t just look at premiums—review whether your preferred providers and medications remain covered affordably. - Plan Ahead Financially
Healthcare is one of the largest and fastest-growing expenses in retirement. Building flexibility into your retirement plan ensures you’re ready to handle potential premium increases and benefit changes.
How Winthrop Partners Helps You Prepare
At Winthrop Partners, we understand that retirement planning and Medicare planning go hand-in-hand. Rising healthcare costs can quickly eat into savings, but with the right strategy, you can protect your retirement lifestyle.
Our team helps clients:
- Anticipate Medicare changes and integrate them into long-term financial plans.
- Compare healthcare options during enrollment periods.
- Align retirement savings and investment strategies with rising healthcare needs.
The 2026 Medicare Annual Enrollment Period will bring new complexities, but you don’t have to navigate them alone. By working with an experienced advisor, you can make informed choices and stay confident about your financial future.

Thomas Saunders is the Managing Partner of Winthrop Partners. Prior to founding Winthrop Partners, Tom was Senior Vice President at what is now JP Morgan. His career includes senior and executive roles at Brown Brothers Harriman and First Niagara Bank, a top 25 Bank. Click here to contact Thomas Saunders about your investment and planning requirements.