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Legacy Insights: Key Questions to Ask During Open Enrollment

Legacy Insights: Key Questions to Ask During Open Enrollment

November 07, 2025

Your Annual Medicare Review: Key Questions to Ask During Open Enrollment

Each fall, from October 15 through December 7, Medicare Open Enrollment gives retirees and pre-retirees a critical opportunity to review their health coverage and make adjustments for the coming year. Even if you’re satisfied with your current plan, changes to premiums, drug formularies, and provider networks can have a real financial impact.

At Legacy Tree Financial, we remind clients that Medicare decisions aren’t just about health insurance — they’re part of a broader retirement income and tax strategy. Here are key questions to guide your annual review so your coverage continues to support your long-term goals.


1. Have My Health Needs Changed This Year?

Health conditions can evolve quickly. A new diagnosis, prescription, or planned procedure may alter which benefits you need.
Ask yourself:

  • Do I have new prescriptions or specialists?

  • Have my out-of-pocket costs been higher or lower than expected?

  • Have I moved or begun spending part of the year in another state?

If so, it may be time to reassess whether your current coverage still fits your needs.


2. Did My Plan Make Any Changes for Next Year?

Every fall, plans send an Annual Notice of Change (ANOC) by September 30, outlining updates for the coming year.
Pay attention to:

  • Premium or deductible changes

  • Updates to provider or pharmacy networks

  • Prescription drugs that move to higher cost tiers

Even small adjustments can have a meaningful impact on your total healthcare cost.


3. What Will My Out-of-Pocket Costs Look Like?

Don’t focus solely on premiums. Review the full cost picture:

  • Monthly premiums

  • Annual deductibles

  • Copays and coinsurance

  • Out-of-pocket maximums

Understanding your total annual healthcare costs helps you plan your retirement cash flow more accurately.


4. How Does My Prescription Coverage Compare to My Current Medications?

Use the Medicare Plan Finder or ask your pharmacist to verify:

  • Are all current medications covered?

  • Have any changed tiers or coverage levels?

  • Are there preferred pharmacies that lower costs?

A mismatch between your medication list and your plan’s formulary can create unexpected expenses.


5. Have My Providers or Hospitals Changed Networks?

Before renewing, confirm your primary care physician, specialists, and hospitals remain in-network. Losing access mid-year can be both disruptive and costly, especially if you live or travel across multiple states.


6. How Does My Medicare Coverage Fit into My Overall Retirement Plan?

Healthcare is one of the largest expenses in retirement. Consider:

  • How premiums and out-of-pocket costs fit into your income plan

  • Whether to use HSA funds, savings, or Social Security for healthcare costs

  • How healthcare expenses may affect your taxable income and RMD strategy

Aligning your healthcare and financial plans helps minimize tax surprises and preserve income longevity.


7. Do I Need to Add or Adjust Supplemental Coverage?

You may choose:

  • Medigap (Supplemental Insurance) — helps cover deductibles and coinsurance for Original Medicare

  • Medicare Advantage (Part C) — includes hospital and medical coverage, and sometimes dental, vision, and hearing

Even if satisfied, review whether:

  • Your coverage remains cost-effective

  • You’ve relocated or had income changes

  • Your plan still provides adequate out-of-state protection

Remember, Medigap rules differ by state, and underwriting may apply if you change plans later.


8. Am I Maximizing My Health Savings and Tax Efficiency?

If you’re still working and have a Health Savings Account (HSA):

  • You must stop contributions the month before Medicare begins to avoid IRS penalties (6% excise tax).

  • You can still use existing HSA funds tax-free for qualified medical expenses, including Medicare premiums (but not Medigap).

Coordinating HSAs, RMDs, and healthcare costs can improve your long-term tax efficiency.


9. Who Can Help Me Evaluate My Options?

While Legacy Tree Financial does not sell or endorse any specific Medicare plans, we collaborate with trusted professionals to ensure your coverage decisions align with your financial plan.
Consider consulting:

  • A licensed Medicare insurance specialist for plan comparisons

  • Your financial planner for income and tax coordination

  • Your healthcare providers to confirm network details

Working with professionals helps ensure decisions are informed, compliant, and aligned with your goals.


Final Thoughts

Medicare Open Enrollment isn’t just an administrative task — it’s an annual checkpoint for your overall retirement strategy. Reviewing your coverage, costs, and healthcare needs helps protect your income and support peace of mind.

At Legacy Tree Financial, we help clients align health, wealth, and longevity strategies so they can enjoy retirement confidently. To integrate healthcare costs into your financial plan, schedule a personalized retirement review today.


Disclosure

This content is for educational purposes only and should not be considered medical, tax, or investment advice. Legacy Tree Financial does not sell or represent Medicare plans. Information provided is general and may not apply to your circumstances.
Always consult qualified healthcare, tax, and financial professionals before making Medicare or retirement planning decisions.


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