How to Reduce the Cost of Tax-Deductible Health Insurance Premiums

Despite the high cost of health insurance, there are a few tax advantages that may allow you to reduce your monthly payments and deduct some of your medical expenses. The advantages of tax benefits have been amplified by recent federal income tax laws that took effect in 2021. 

Tax-Deductible Health Insurance

These updated regulations may prove to be particularly advantageous for individuals who have lost their jobs or those who have paid for their self-employed health insurance through a tax-deductible plan.

Even if you work in the gig economy, you can be eligible for additional benefits or self-employment income when filing your income tax return. 

Tax-deductible Premiums for Independent Contractors

Your health insurance premiums are tax deductible even if you are self-employed and ineligible for a company-sponsored health plan.

It is possible to claim the allowance on Schedule 1 on Form 1040 without organizing. 

The maximum allowance is the net self-employment benefits that you submitted on Form C.

Even if you had employer-provided health insurance at the beginning of the year but later lost your job and went into business for yourself.

It is possible that you may have the option to deduct a portion of the premiums you paid during months when you were unable to utilize employer-sponsored coverage. 

Medical Costs are Classified as a Deduction in

Health insurance premiums can be written off as a medical expense on your taxes if you budget your spending.

You may deduct medical expenses after they reach 7.5% of your adjusted gross income or greater.

If you have health insurance through your job and pay tax premiums using pre-tax funds, you cannot go on a second date and claim those fees as a medical expense.

Yet, there are some circumstances where individuals may not be aware of this and pay for employer-based insurance with the expectation that it will be tax deductible after tax. 

Some retirees may lose out on a proper deduction by failing to disclose that they include medical insurance in their post-charge pension.

Individuals who are 65 years of age or older and own a Health Savings Account (HSA) are eligible to withdraw money from their accounts tax-free in order to pay for Medicare Part B, Part D, and Medicare Advantage expenses.

By utilizing the record to pay both your and your partner’s premiums, you can avoid paying taxes on the withdrawal. 

Additionally, if your Social Security benefits are being utilized to pay for your Medicare premiums, you can withdraw funds from your HSA without incurring any tax liability to cover the expenses.

You cannot make new HSA commitments after signing up for Medicare, but you are still able to use money that has already been deposited to pay for Medicare expenses.

There are potential tax benefits available for individuals who are paying long-term care insurance premiums. Depending on your circumstances, you may be able to receive a tax deduction or utilize untaxed funds to cover these costs. 

If you plan ahead, you may even be able to include the expense of long-term care insurance within your medical cost allowance, as long as it falls within the 7.5% higher gross pay margin for clinical costs.

Additionally, withdrawing money from your health savings account is also a tax-free option for covering long-term care expenses. How many long-term care costs qualify for the rebate will depend on your age. If you’re over the indicated age, you’ll get a greater discount. 


To make health insurance for self-employed investments less stressful, make sure that tax write-off are included under insurance tax deductions. If you have any queries about this, you can contact FlyFin or use a 1099 tax calculator.

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