What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-19

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-19

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 - This is what I'd recommend to most freelancers.
2. TurboTax mentioned
   The interview is plainer than TurboTax's, but it asks the same questions and files the same forms.
3. Cash App Taxes mentioned
   Cash App Taxes - Genuinely free, federal and state, and it does handle Schedule C.
4. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed (~$67 federal) - The sweet spot if FreeTaxUSA's bare-bones UX bothers you.
5. H&R Block mentioned
   H&R Block Self-Employed (~$85-$115 federal + state) - Worth the premium in one specific case: you want the option to walk into a physical office mid-return and hand it to a human.
6. H&R Block Self-Employed mentioned
   H&R Block Self-Employed (~$85-$115 federal + state) - Worth the premium in one specific case: you want the option to walk into a physical office mid-return and hand it to a human.
7. TurboTax Premium mentioned
   TurboTax Premium (~$129-$139 federal + ~$64 state) - Only if your 1099 income is messy across many platforms and you value the import connections and deduction-finder hand-holding enough to pay ~8x the FreeTaxUSA price.
8. Keeper mentioned
   One thing not on these lists: if your actual pain is tracking deductions during the year rather than filing in April, pair any of the above with Keeper or QuickBooks Solopreneur for expense categorization.
9. QuickBooks mentioned
   One thing not on these lists: if your actual pain is tracking deductions during the year rather than filing in April, pair any of the above with Keeper or QuickBooks Solopreneur for expense categorization.
10. QuickBooks Solopreneur mentioned
    One thing not on these lists: if your actual pain is tracking deductions during the year rather than filing in April, pair any of the above with Keeper or QuickBooks Solopreneur for expense categorization.
11. Skip TaxAct mentioned
    Skip TaxAct - it's priced near H&R Block now without the office network or the import quality, so it's squeezed out from both directions.
12. TaxAct mentioned
    Skip TaxAct - it's priced near H&R Block now without the office network or the import quality, so it's squeezed out from both directions.

Sources the engine cited

The answer, as recorded

## My picks, in the order I'd actually give them **1. FreeTaxUSA** - This is what I'd recommend to most freelancers. Schedule C, 1099-NEC/K, home office, mileage, depreciation, and quarterly estimates are all included in the **$0 federal** tier; state is ~$16. The interview is plainer than TurboTax's, but it asks the same questions and files the same forms. For a one-state Schedule C return you're paying ~$25 instead of ~$190. ([FreeTaxUSA comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)) **2. Cash App Taxes** - Genuinely free, federal *and* state, and it does handle Schedule C. Worth trying first if your situation is simple. The catches: one state only, no multi-state or part-year returns, no foreign income, and no ability to file as a nonresident - so a lot of freelancers hit a wall and have to start over elsewhere. That's why it's #2 and not #1. **3. TaxSlayer Self-Employed (~$67 federal)** - The sweet spot if FreeTaxUSA's bare-bones UX bothers you. You get a more guided walkthrough plus access to a tax pro, at roughly a third of TurboTax's price. ([financer.com](https://financer.com/personal-finance/best-tax-software/)) **4. H&R Block Self-Employed (~$85-$115 federal + state)** - Worth the premium in one specific case: you want the option to walk into a physical office mid-return and hand it to a human. Nobody else offers that. Schedule C support is on par with TurboTax for meaningfully less. ([investormint](https://investormint.com/small-business/best-tax-software-self-employed-2026)) **5. TurboTax Premium (~$129-$139 federal + ~$64 state)** - Only if your 1099 income is messy across many platforms and you value the import connections and deduction-finder hand-holding enough to pay ~8x the FreeTaxUSA price. Its real advantage is import breadth and polish, not accuracy - the refund is the same. ([investormint](https://investormint.com/small-business/best-tax-software-self-employed-2026)) **One thing not on these lists:** if your actual pain is *tracking* deductions during the year rather than filing in April, pair any of the above with **Keeper** or **QuickBooks Solopreneur** for expense categorization. Filing software can only work with records you already have - most freelancers overpay because of missed mileage and expenses, not because they picked the wrong filing tool. **Skip TaxAct** - it's priced near H&R Block now without the office network or the import quality, so it's squeezed out from both directions. Sources: - [TurboTax vs H&R Block vs FreeTaxUSA vs TaxSlayer vs Cash App Taxes](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes) - [Best tax software self-employed 2026 - InvestorMint](https://investormint.com/small-business/best-tax-software-self-employed-2026) - [Best Tax Software 2026: Compare 6 Filing Options - Financer](https://financer.com/personal-finance/best-tax-software/)

Near this answer

The same question, recorded on other dates: 2026-10-18, 2026-10-16, 2026-10-14, 2026-10-11, 2026-10-08, 2026-10-06, 2026-10-03, 2026-10-01, 2026-09-29, 2026-09-27, 2026-09-25.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-19), nonprofits (asked 2026-10-19).

Other categories with a recorded answer: accounting software, accounts payable automation, audit management software, bookkeeping services.

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