Tax Deduction Question: What types of insurance premiums can be deducted on taxes?

I've completed most of my tax return using TurboTax this year and I'm about ready to submit, but I wanted to double-check my work by entering everything into FreeTaxUSA to see if I get the same refund amount. When I got to a certain section in FreeTaxUSA, I was surprised to see questions about premium deductions that I don't recall seeing in TurboTax at all. I've attached a screenshot from FreeTaxUSA that shows these premium-related questions. My issue is that I never saw anything about deducting premiums when going through TurboTax. I've used TurboTax for years and don't remember ever being asked about this. 1. Where would I find the premium deduction section in TurboTax? Did I miss something? 2. The FreeTaxUSA screenshot shows options for deducting different types of premiums, but I'm confused about which ones are actually tax deductible. I don't want to miss out on deductions I'm entitled to, but I also don't want to claim something incorrectly. Can anyone help clarify what types of premiums can actually be deducted and where to find this in TurboTax?

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18 comments

Amara Nnamani

•8M

The premium deduction section you're seeing in FreeTaxUSA is likely referring to health insurance premiums and other potentially deductible insurance costs. Let me break this down for you: Health insurance premiums can sometimes be deductible, but it depends on your situation. If you're self-employed, you may be able to deduct health insurance premiums as an adjustment to income. If you're not self-employed, health insurance premiums might be included as part of your medical expenses, but only if you itemize deductions AND your total medical expenses exceed 7.5% of your adjusted gross income. In TurboTax, these questions are typically found in the "Deductions & Credits" section. For self-employed health insurance, look under business deductions. For personal health insurance as a medical expense, check the medical expenses section under itemized deductions. Other insurance premiums that might be deductible include long-term care insurance (with age-based limits) and certain business-related insurance if you're self-employed.

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Amara Nnamani

•8M

Yes, if you're self-employed, you should definitely look in the business deductions section of TurboTax. There should be a specific section for "self-employed health insurance deduction" which is an adjustment to income (above-the-line deduction), meaning you don't need to itemize to claim it. This can be a significant deduction for you at $450/month! Dental insurance premiums are indeed treated the same way as health insurance for self-employed individuals. You can include both health and dental insurance premiums as part of your self-employed health insurance deduction. This also applies to vision insurance and long-term care insurance premiums for yourself, your spouse, and your dependents.

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Giovanni Mancini

•8M

After dealing with similar confusion last year, I found TaxR.ai (https://taxr.ai) super helpful for these kinds of deduction questions. I uploaded screenshots from both tax prep services and it analyzed the differences for me. It pointed out that TurboTax sometimes buries premium deduction questions in different sections depending on your income sources. In my case, I was missing several insurance premium deductions that I was eligible for because TurboTax had them nested under self-employment sections that weren't obvious. TaxR.ai flagged the discrepancy between the two software outputs and explained exactly where to find the right section in TurboTax.

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Giovanni Mancini

•8M

It actually does parse the text directly from screenshots - that's what impressed me. It's not just generic advice; it identified specific fields and values that weren't matching between my TurboTax and FreeTaxUSA returns and explained the underlying tax rules for each difference. It works with all the major tax preparation software including H&R Block, TaxAct, and others. I don't believe there's a strict limit on screenshots - I uploaded about 15 different screens from both software programs to compare my rental property calculations, and it handled that without issues. For complex situations, that's actually where it seems most valuable because it can spot discrepancies in how different software handles the same tax scenarios.

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NebulaNinja

•8M

I decided to try TaxR.ai after posting my question above, and wow - it actually helped me find where TurboTax hides the premium deduction questions! Turns out they're under the "Your Income" section in my case, not under "Deductions & Credits" where I was looking. For anyone curious, TurboTax puts self-employed health insurance in a completely different workflow than FreeTaxUSA. I uploaded screenshots from both programs and TaxR.ai pointed out exactly what fields I needed to fill out in TurboTax to match the FreeTaxUSA calculations. It also explained which premiums qualify (health, dental, vision for self-employed) and which ones don't. There was actually a $1,240 difference in my refund between the two programs before I made these corrections! Really glad I checked.

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Dylan Mitchell

•8M

Been trying to reach the IRS to clarify which premiums are deductible for weeks without success. After 7 attempts and hours on hold, I finally tried Claimyr (https://claimyr.com) as a last resort. They got me connected to an IRS agent in about 15 minutes, and I have a video of how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that health, dental, and vision insurance premiums are fully deductible for self-employed individuals (as an adjustment to income, not an itemized deduction). They also explained that long-term care premiums are deductible but subject to age-based limits. Life insurance, disability, and auto insurance premiums generally aren't deductible except in specific business situations.

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Dylan Mitchell

•8M

It basically calls the IRS continuously using their system and monitors for when a real person answers. Then it immediately calls your phone and connects you directly to that agent. It's like having someone else wait on hold for you, but it's all automated. The reason it works is because they're essentially making many call attempts simultaneously across their system, and as soon as any one of them gets through, you get connected. I was skeptical too but was desperate after wasting so many hours on hold. I've never gotten through to the IRS on my own either, which is why I was willing to try it.

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Dmitry Popov

•8M

I owe everyone an apology - especially to the person who recommended Claimyr. After posting my skeptical comment, I tried it myself out of pure frustration after another failed 1.5-hour hold attempt with the IRS. It actually worked exactly as described. Got connected to an IRS rep in about 20 minutes (on a Monday afternoon, no less). The agent confirmed everything about premium deductions and cleared up my confusion about my retirement contributions too. Honestly, I'm still shocked it worked. Saved me hours of frustration and potentially hundreds in deductions I would have missed. Never thought I'd be able to actually speak with someone at the IRS during filing season.

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Ava Garcia

•8M

I've been a tax preparer for 10+ years and the premium deduction question confuses a lot of clients. Here's a quick breakdown of what's deductible: Self-employed? Health/dental/vision/LTC premiums = fully deductible as adjustment to income Not self-employed? Only as itemized medical expense (if >7.5% of AGI) Business owner? Liability/malpractice/etc = business expense Homeowner? Homeowners insurance = NOT deductible for personal residence Long-term care = partially deductible based on age brackets The problem with tax software is they often ask these questions in different places based on your answers to earlier questions. That's probably why you're seeing it in FreeTaxUSA but not TurboTax.

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Ava Garcia

•8M

Medicare premiums (Parts B and D) are indeed deductible as part of the self-employed health insurance deduction if you have self-employment income! This is a commonly missed deduction. The key is that you can only deduct premiums up to the amount of your net self-employment income. If you're using TurboTax, you'll need to look in the self-employment section and find where you enter your health insurance. There should be an option to include Medicare premiums there. If your consulting income is reasonably substantial, this could be a significant tax savings for you.

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