What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-14

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-14

Coverage: Claude (Anthropic) with web search. Other engines not included.

The question asked, verbatim: best tax preparation software for freelancers

Brands named, in the order the engine gave

1. FreeTaxUSA recommended
   FreeTaxUSA - the default pick for most freelancers.
2. TurboTax recommended
   The interface is plainer than TurboTax's, but the math is the same math.
3. H&R Block recommended
   H&R Block Self-Employed - the best balance if you want guidance.
4. H&R Block Self-Employed recommended
   H&R Block Self-Employed - the best balance if you want guidance.
5. TurboTax Premium recommended
   TurboTax Premium - worth it only if your return is messy.
6. TaxSlayer Self-Employed recommended
   TaxSlayer Self-Employed - the middle-price alternative.
7. S-corp recommended
   If you've formed an S-corp, have employees or contractors of your own, owe multi-state taxes, or are behind on quarterlies, skip all of the above.
8. Keeper mentioned
   If you're not already tracking expenses and mileage, something like Keeper or QuickBooks Solo (or honestly, a dedicated business checking account and a spreadsheet) will find you more deductions than upgrading from FreeTaxUSA to TurboTax ever will.
9. QuickBooks mentioned
   If you're not already tracking expenses and mileage, something like Keeper or QuickBooks Solo (or honestly, a dedicated business checking account and a spreadsheet) will find you more deductions than upgrading from FreeTaxUSA to TurboTax ever will.

Sources the engine cited

The answer, as recorded

Here's what I'd actually recommend, in order: **1. FreeTaxUSA - the default pick for most freelancers.** Federal filing is free including Schedule C and Schedule SE, with roughly $15 per state return. It handles 1099-NEC income, home office, mileage, QBI deduction, and quarterly estimate vouchers. The interface is plainer than TurboTax's, but the math is the same math. Unless your situation is genuinely complicated, paying $100+ elsewhere buys you hand-holding, not a better refund. ([walletgrower.com](https://walletgrower.com/compare/turbotax-vs-hr-block-vs-freetaxusa)) **2. H&R Block Self-Employed - the best balance if you want guidance.** Around $85 federal plus ~$37 per state. It does nearly everything TurboTax does for roughly half the price, and it's the only one of these with physical offices, so if your return goes sideways you can hand it to a human in person. ([ifeeltech.com](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa)) **3. TurboTax Premium - worth it only if your return is messy.** Roughly $129 federal plus state. The Schedule C interview genuinely is the best in the industry, and it's the strongest option if you're also juggling investments, crypto, rental property, or multi-state income. For a single 1099 and a few expenses, you're overpaying. ([quarterly1099.com](https://quarterly1099.com/articles/turbotax-self-employed-review.html)) **4. TaxSlayer Self-Employed - the middle-price alternative.** Cheaper than H&R Block with a full self-employment feature set, including quarterly estimate support. Less polished, fewer support options, but a reasonable pick if FreeTaxUSA feels too bare and TurboTax too expensive. ([unlike.net](https://unlike.net/best-tax-software-self-employed-2026/)) **5. A CPA or enrolled agent - not software, but say it once.** If you've formed an S-corp, have employees or contractors of your own, owe multi-state taxes, or are behind on quarterlies, skip all of the above. The few hundred dollars buys planning, not just filing, and that's where the actual savings are for freelancers. One thing that matters more than which of these you pick: **bookkeeping during the year.** Tax software only processes numbers you feed it. If you're not already tracking expenses and mileage, something like Keeper or QuickBooks Solo (or honestly, a dedicated business checking account and a spreadsheet) will find you more deductions than upgrading from FreeTaxUSA to TurboTax ever will. Caveat on the prices: they're from this season's comparisons and every vendor raises them as April approaches - TurboTax especially. Check the current price before you start, and file early. Sources: - [https://walletgrower.com/compare/turbotax-vs-hr-block-vs-freetaxusa](https://walletgrower.com/compare/turbotax-vs-hr-block-vs-freetaxusa) - [https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa) - [https://quarterly1099.com/articles/turbotax-self-employed-review.html](https://quarterly1099.com/articles/turbotax-self-employed-review.html) - [https://unlike.net/best-tax-software-self-employed-2026/](https://unlike.net/best-tax-software-self-employed-2026/)

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Answer Watch records what one AI answer engine said on one date, nothing more. Each page names the engine and the model, carries the date the question was asked, and lists the brands that appeared in the answer in the order the engine gave them, with the sources it cited. It is a measurement, not a ranking, not a recommendation and not a claim about the world. Brands that did not appear in an answer are not named on any public page. Coverage: Claude (Anthropic) with web search. Other engines not included.