Companies like TurboTax and H&R Block advertise free filing, but most users don’t qualify for the truly free version. Once you start entering your information, you’re often prompted to upgrade for things like:

• Filing a state return ($25–$50)
• Claiming the Earned Income Tax Credit or Child Tax Credit ($30–$60)
• Reporting self-employment or gig income ($60–$120)
• Accessing audit protection or live support ($40–$100)

    These upsells are triggered after you’ve already entered your data, making it hard to back out. The result? Many filers end up paying $100–$250 for a return they thought would be free.

    Beyond the software fees, the real danger is what these platforms don’t catch. Automated systems often miss nuanced deductions or credits that could significantly reduce your tax bill or increase your refund. According to a 2024 NerdWallet analysis, over 100 million Americans qualified for IRS Free File, but only 3.3 million used it. That means roughly $4 billion was spent unnecessarily—about $40 per person on average. But that’s just the software cost. The real losses come from missed opportunities.

1. State Sales Tax – Especially valuable in states with no income tax. You can deduct sales tax using IRS tables or actual receipts, up to $10,000 with other SALT deductions.
2. Reinvested Dividends – These increase your investment’s cost basis, reducing taxable gains. Ignoring them can lead to overpaying capital gains tax.
3. Out-of-Pocket Charitable Contributions – Small expenses like mileage, supplies, or stamps for volunteer work are deductible if you itemize.
4. Student Loan Interest – Up to $2,500 is deductible, even if someone else paid it, as long as you’re not a dependent.
5. Moving Expenses (Military Only) – Active-duty military can deduct unreimbursed moving costs with proper documentation.
6. Child and Dependent Care Credit – Covers 20–35% of care costs (up to $3,000 for one child, $6,000 for two or more), including camps and babysitters.
7. Earned Income Tax Credit (EITC) – Refundable credit up to $7,830 for low-to-moderate earners. Many eligible filers miss it entirely.
8. Jury Pay Given to Employer – If you hand over jury pay to your employer, you can deduct it to avoid being taxed on it.
9. Refinancing Mortgage Points – Points paid during refinancing can be deducted over the life of the loan—or all at once if you refinance again or sell.
10. Medical Expenses – Deduct costs exceeding 7.5% of AGI, including travel, lodging, therapy, and some alternative treatments. HSA contributions are also deductible.

Jessica, a single mother of two working part-time, used a free tax app that didn’t prompt her to check for the Earned Income Tax Credit. She earned $28,000 last year and didn’t owe any taxes, so she assumed there was no refund coming. In reality, she qualified for over $5,600 in refundable credits. A professional would have caught this. The app didn’t.

Carlos, a retired teacher, sold mutual fund shares to help with home repairs. He used a free filing tool and reported the full sale price as capital gains, unaware that his reinvested dividends had increased his cost basis. He overpaid nearly $1,200 in taxes. A tax pro would have adjusted the basis and saved him that money.

    Free software isn’t always free—and it’s rarely thorough. For the average taxpayer, the cost of missed deductions, credits, and strategic planning can far outweigh the price of professional help. If your return includes kids, student loans, investments, gig work, or even charitable giving, it’s worth having a real person review it. You might be leaving hundreds—or thousands—on the table.

Let’s make sure that doesn’t happen this year.