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Emma Bethea | Feb 19 2025 19:35

Maximize Tax Savings with Insurance Deductions

Many taxpayers overlook valuable insurance-based tax deductions that can lead to significant savings and improved financial health, especially during tax season. Understanding these deductions can reveal surprising opportunities, such as deducting certain insurance premiums and medical-related expenses, if managed correctly.


Health Savings Accounts (HSAs)

Health Savings Accounts offer a great tax advantage. Contributions to an HSA are tax-deductible, even for those who don’t itemize deductions. They provide a triple tax benefit:

  • Contributions are deductible, reducing taxable income.
  • The account grows tax-deferred, and interest or earnings aren't taxed annually.
  • Withdrawals for qualified medical expenses are tax-free.

Medical Expenses

Unreimbursed medical costs exceeding 7.5% of your adjusted gross income (AGI) may be deductible. Various expenses can qualify:

  • Treatments and surgeries.
  • Prescription medications.
  • Necessary medical travel costs.

An example of this in practice would be a year filled with unexpected medical procedures that push your expenses beyond the standard threshold, allowing for deductions.


Deductions for the Self-Employed

Self-employed individuals can take advantage of tax deductions on premiums they pay for health, dental, and long-term care insurance. Additionally, business-related insurances such as vehicle insurance for work purposes are deductible.

Take, for example, Alex, a freelance graphic designer who deducts her health insurance and the insurance she uses for her business vehicle.


Disability Insurance

For the self-employed, disability insurance premiums can be deductible, but only if the policy covers business overhead expenses. Unfortunately, personal disability insurance does not qualify.

For instance, if Jordan, a self-employed photographer, purchases a disability insurance policy that covers her studio's rent and utility bills, she can deduct these premiums.


Unemployment and Workers' Compensation

It's crucial to understand that unemployment benefits are taxable, whereas workers' compensation benefits are usually not. Accurate reporting is vital to avoid discrepancies during tax filing.


Qualified Life Insurance

Generally, life insurance premiums aren't deductible. However, they can be if they're business-related. The policyholder must be an employee or corporate officer, and the business can't be the beneficiary.

Consider a corporate scenario where a company purchases a life insurance policy for its CEO, who is also a shareholder. The company provides the premium coverage as part of the CEO's compensation package.


Maximizing insurance-based tax deductions requires awareness and diligent documentation. Analyzing your insurance expenses and consulting a tax professional can help ensure you're leveraging all available deductions.

Have questions about your insurance coverage? Reach out today for policies that protect you and those you love.

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