Should a Large Medical Expense Change Which Account Funds Your Retirement Spending?

Ross Marino |

A substantial medical or dental bill needs to be paid, and you have several accounts that could cover it. You want care to proceed and enough money left for the weeks ahead. Then a possible tax deduction enters the conversation: could this be a good year to use your traditional IRA?

It may deserve a closer look. But a deductible bill does not automatically cancel an equally sized taxable withdrawal. The money you raise can change the deduction you were counting on. Start with the care you need, then compare how each funding choice affects taxes and the resources that remain.

How much of the bill can actually reduce your taxes?

For 2026 federal planning, eligible unreimbursed medical and dental expenses enter the itemized-deduction calculation only to the extent they exceed 7.5% of adjusted gross income, or AGI. The floor applies to eligible expenses for the year, not separately to each bill. Payment timing and reimbursements matter; a bill received this year is not necessarily an expense paid this year. [1]

Medical necessity alone does not establish full deductibility. Some care costs and premiums qualify only under specific rules, and others do not. Even an eligible amount above the floor may produce no additional federal tax benefit if your total itemized deductions do not exceed your available standard deduction. [2]

AGI and taxable income are different steps. The medical itemized deduction reduces taxable income after AGI is determined. It does not remove an IRA withdrawal from AGI the way an applicable income exclusion would. That distinction is why a deduction can affect income-based calculations. [3]

Why can the account you choose change the deduction?

The taxable portion of a traditional IRA distribution generally enters ordinary income. The gross withdrawal and its taxable portion may differ when nondeductible contributions are involved; your tax professional determines the allocation. [4] If the withdrawal increases AGI, the 7.5% floor rises too. With the same eligible expenses, less may remain above that floor.

Conditional comparison: the same eligible bill

Use existing cash

No new income from spending the cash itself

Medical deduction tested against the existing income picture.

Take a taxable IRA withdrawal

AGI rises

The medical-expense floor also rises.

Eligible unreimbursed expenses minus the applicable AGI floor, subject to itemization.

Only a positive excess can qualify. Taxable-account sales require a separate proceeds-versus-gain calculation.

This comparison assumes the IRA distribution adds income beyond what you otherwise planned. Using money from a withdrawal already included in the year’s plan does not create a second withdrawal. Likewise, paying from cash today and taking an extra taxable distribution to refill it this year can bring the income effect back.

What changes when you compare all three sources?

Existing cash offers a straightforward starting point. Spending the cash itself creates no new income, although interest earned on it remains a separate tax matter. Ask how much accessible cash remains after paying for care, ordinary bills, and upcoming taxes.

A taxable-account sale requires a different comparison. Gross proceeds supply cash; the gain or loss depends on proceeds and adjusted cost basis. Selling enough to pay the bill does not mean the entire sale amount becomes taxable income. The selected holdings and gains or losses elsewhere on the return affect the result. [5]

An IRA withdrawal may preserve your cash reserve, but it may also increase the tax cost when determining how much must leave the account. Withholding reduces the cash delivered; it does not reduce the taxable portion of the distribution. A deduction may soften the tax cost without eliminating it.

Dovetail Principle: Information Should Show What Changes for You

The useful information is the difference each funding choice makes: cash available to pay for care, income added, deduction actually usable, and resources remaining. Seeing those changes together helps you choose without treating the size of the medical bill as a tax answer.

How do you preserve room for recovery and ordinary life?

Accessible reserves help absorb another unexpected expense without forcing a hurried investment sale. [6] Keep the reserve tied to your circumstances: follow-up visits, transportation, help at home, and regular spending may continue after the large bill is paid. A blend of sources may preserve that margin better than using one account alone.

If an HSA is available, qualified tax-free reimbursement deserves brief consideration. Expenses reimbursed by insurance or a tax-advantaged arrangement, including a tax-free HSA distribution, cannot also supply the same medical deduction. Your tax professional should confirm eligibility and prevent double counting. [1]

Have your tax professional compare the actual deduction, income consequences, and complete after-tax cash result for the same care expense, including applicable state rules. Your advisor can connect that result to reserves and remaining investments. Medical professionals guide care decisions; don't delay or choose care to get a deduction. Choose the account, or combination, that funds care while preserving the cash and flexibility ordinary life still needs.

For the broader withdrawal decision, read How Should You Decide Whether to Spend Cash, Taxable Accounts, or IRAs First?.

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

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Notes

  1. Publication 502 (2025), Medical and Dental Expenses, Internal Revenue Service.
  2. Don’t Overlook These 6 Medical Tax Deductions, AARP.
  3. Above-the-Line Tax Deductions Anyone Can Take, AARP.
  4. Publication 590-B (2025), Distributions from Individual Retirement Arrangements (IRAs), Internal Revenue Service.
  5. Cost Basis Basics, FINRA.
  6. Financial Foundations, FINRA.

Disclosure

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