When it comes to filing taxes, getting the best returns is not about skill—it's about what you know. Unfortunately, many taxpayers miss out on deductions and credits simply because they just aren't aware of them. Several of the most overlooked deductions pertain to health, medical expenses, and insurance premiums.

For the most part, the Trump tax bill—2017 Tax Cuts and Jobs Act (TCJA)—seems to leave most of the deductions discussed below unchanged with one exception, the medical expenses. Read on for some insurance-based tax deductions you may be missing. 

Key Takeaways

  • Getting the most of your tax deductions and credits is all about having the right knowledge—many people miss out on these because they’re unaware of them.
  • Oft-missed deductions include those related to insurance premiums, medical expenses, and other health-related costs.
  • Disability insurance is an important, often-missed, but complex tax deduction.
  • Health Savings Account (HSA) contributions are tax-free up to a predetermined cap.
  • Life insurance and business-related insurance premiums also may qualify for deductions. 

Disability Insurance

Disability insurance is probably the most common type of premium that is overlooked as a tax deduction. The deductibility of these premiums, is complicated, however. The Internal Revenue Service (IRS) permits self-employed taxpayers to deduct "overhead insurance that pays for business overhead expenses you have during long periods of disability caused by your injury or sickness." But "you cannot deduct premiums for a policy that pays for lost earnings due to sickness and disability." 

If you deduct the premium, any benefits paid from the policy will be considered taxable income. By contrast, policy benefits will not be taxable if you do not deduct the premium, and some taxpayers use this arrangement so that they can receive tax-free benefits if they become disabled. Benefits are also taxable if your employer paid for your disability insurance, rather than if you bought it yourself with your own after-tax dollars. 

There are several specific rules you must follow to ensure that you qualify to deduct health insurance-related expenses, based on your employment status, whether or not you itemize deductions, and whether you’ve paid your premiums using pre- or post-tax dollars. 

Health Savings Accounts

Other insurance-related tax perk that people without access to traditional group health coverage should be aware of is a health savings account (HSA), which combines a tax-advantaged savings element with a high-deductible health insurance policy. 

All HSA contributions, up to the maximum permitted by law, are tax-deductible, even for those who do not itemize, and earnings accumulate tax-free. All proceeds withdrawn from the account are tax-free, provided they are used to pay for qualified medical expenses.

Medical Expenses

The only medical expenses that are deductible have been those that are more than 10% of adjusted gross income. This means that few taxpayers accumulate enough unreimbursed bills in one year to qualify for the deduction. Under the new tax law, starting with the 2017 tax year, the threshold dropped to 7.5%. But the level returns to 10% for the 2019 tax year. 

If you have substantial medical bills pending, you can boost your deduction by scheduling other medical procedures or expenses in the same year. One caveat is that if you get a check the following year from your insurance company, you will have to declare the amount of the deduction that was reimbursed as income the following year. 

For example, if you deducted $17,000 for surgery in one year and your insurance company sent you a $10,000 check for the surgery the next year, that amount would have to be declared as income in the year the check arrives. 

If there's a chance you may get medical expenses covered by your insurance company in the future, do not declare this deduction until you know whether the insurance company will reimburse you. You can always submit an amended return for the year you would have received the deduction if your insurance claim is denied.

Unemployment/Workers' Compensation

It is important to distinguish unemployment compensation from a state unemployment agency from workers' compensation, which is awarded to workers who cannot perform their duties as a result of an injury. 

Unemployment benefits are always taxable, as they are considered a replacement of regular earned income and should be reported on IRS Form 1040. Workers' compensation is never declarable as income.

Deductions for the Self-Employed

Self-employed taxpayers and other business entities can deduct business-related insurance premiums of any kind, including health and dental insurance premiums, as well as legal and liability coverage. Vehicle insurance can also be deducted if the taxpayer elected to report actual expenses and is not taking the standard mileage rate. 

Life Insurance

Life insurance premiums are deductible as a business-related expense (if the insured is an employee or a corporate officer of the company, and the company is not a direct or indirect beneficiary of the policy). The death benefit is generally tax-free for individual policy owners. 

Although death benefits for business-related beneficiaries are often tax-free as well, there are certain situations in which the death benefit for corporate-owned life insurance can be taxable. However, employers offering group-term life coverage to employees can deduct premiums they pay on the first $50,000 of benefits (per employee), and amounts up to this limit are not counted as income to the employees. 

Life insurance premiums can also often be deducted for most types of non-qualified plans, such as deferred compensation or executive bonuses. Usually, the premiums are considered compensation for key executives under the rules of these plans. However, in some cases, the deduction cannot be taken until the employee constructively receives the benefit.

Other Qualifying Plans

Nonqualified plans aren't the only type of retirement savings vehicle that can be funded with tax-deductible premiums: 412(i) plans are qualified, defined-benefit plans that can provide substantial deductions for small-business owners looking to catch up on their retirement savings and receive a guaranteed income stream. 

These plans are funded solely with insurance products such as cash value life insurance or fixed annuity contracts, and the plan owner can often deduct hundreds of thousands of dollars in contributions to these plans each year.

Finally, participants in standard qualified plans, such as 401(k) plans, can purchase a limited amount of either term or permanent coverage subject to specific restrictions. But the coverage must be considered "incidental" according to IRS regulations. In any type of qualified defined-contribution plan, the cost of whole life premiums for each participant must be less than 50% of the employer's contribution amount, plus forfeitures.

For term and universal coverage, the limit is 25%. This is the only instance where individuals can purchase life insurance on a tax-deductible basis—assuming the plan is a traditional plan and not a Roth 401(k) plan. Life insurance death benefits paid out of qualified plans also retain their tax-free status, and this insurance can be used to pay the taxes on the plan proceeds that must be distributed when the participant dies.

The Bottom Line

This article only mentions a few of the more commonly overlooked deductions and tax benefits related to insurance for which business and individual taxpayers are eligible. Other deductions relating to compensation, production, depreciation of buildings and equipment are listed on the IRS website in various downloadable instruction manuals.