What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-12

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-12

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 - my default recommendation for most freelancers.
2. you're compared
   There's no capability gap versus the paid tiers for a typical solo Schedule C filer - you're paying TurboTax ~$115 more for a friendlier interview, not a better return.
3. TurboTax compared
   There's no capability gap versus the paid tiers for a typical solo Schedule C filer - you're paying TurboTax ~$115 more for a friendlier interview, not a better return.
4. Cash App Taxes mentioned
   Cash App Taxes - free federal and state, which makes it the cheapest legitimate option if you fit.
5. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - the value middle ground.
6. H&R Block mentioned
   Full Schedule C support, quarterly estimated payment calculation, and self-employment-specific guidance, at meaningfully less than H&R Block or TurboTax.
7. H&R Block Self-Employed mentioned
   H&R Block Self-Employed (~$85 federal + ~$37/state) - pick this over TurboTax if you want a guided experience plus the option to hand the return to a human, including in person.
8. TurboTax Premium mentioned
   TurboTax Premium (~$129 federal, state extra) - the best interview flow, and genuinely worth the premium only if your situation is messy: freelance income plus rentals, crypto, RSUs, or multi-state work.
9. Keeper mentioned
   Keeper - different category, worth naming because it solves the part freelancers actually get wrong: finding deductions.
10. Stripe compared
    It links bank accounts plus Stripe/PayPal/Venmo, classifies transactions business vs.
11. PayPal compared
    It links bank accounts plus Stripe/PayPal/Venmo, classifies transactions business vs.
12. S-corp mentioned
    If you're netting enough that an S-corp election is on the table, that's the point where a CPA beats any of the above on ROI.

Sources the engine cited

The answer, as recorded

**FreeTaxUSA** - my default recommendation for most freelancers. Federal filing is free including Schedule C, Schedule SE, 1099-NEC, home office, and depreciation; state is ~$15. There's no capability gap versus the paid tiers for a typical solo Schedule C filer - you're paying TurboTax ~$115 more for a friendlier interview, not a better return. ([The College Investor](https://thecollegeinvestor.com/20918/freetaxusa-review/), [WalletGrower](https://walletgrower.com/compare/turbotax-vs-hr-block-vs-freetaxusa)) **Cash App Taxes** - free federal *and* state, which makes it the cheapest legitimate option if you fit. The catch is real: no multi-state or nonresident returns, no K-1 income, and it doesn't compute underpayment penalties - which is exactly the thing freelancers who skipped quarterlies run into. Good for a single-state side hustle, not for a full-time business. ([The College Investor](https://thecollegeinvestor.com/39045/cash-app-taxes-review/)) **TaxSlayer Self-Employed** - the value middle ground. Full Schedule C support, quarterly estimated payment calculation, and self-employment-specific guidance, at meaningfully less than H&R Block or TurboTax. Worth it if you want more handholding than FreeTaxUSA but won't pay TurboTax prices. ([unlike.net](https://unlike.net/best-tax-software-self-employed-2026/)) **H&R Block Self-Employed** (~$85 federal + ~$37/state) - pick this over TurboTax if you want a guided experience plus the option to hand the return to a human, including in person. Consistently 20-30% cheaper than the equivalent TurboTax tier for near-identical functionality. ([iFeeltech](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa)) **TurboTax Premium** (~$129 federal, state extra) - the best interview flow, and genuinely worth the premium only if your situation is messy: freelance income *plus* rentals, crypto, RSUs, or multi-state work. For a clean 1099 return it's the same numbers at 8x the price. ([Quarterly1099](https://quarterly1099.com/articles/turbotax-self-employed-review.html)) **Keeper** - different category, worth naming because it solves the part freelancers actually get wrong: finding deductions. It links bank accounts plus Stripe/PayPal/Venmo, classifies transactions business vs. personal year-round, and files at the end. Hard ceiling though - no S-corps, partnerships, multi-member LLCs, or businesses with employees. ([FinanceBuzz](https://financebuzz.com/keeper-tax-review), [The College Investor](https://thecollegeinvestor.com/35362/keeper-tax-review/)) Two notes on timing, since it's September: if you extended, your 2025 return is due **October 15, 2026**, and your Q3 estimated payment was due September 15. Also, published prices are for the current season and typically rise as the April deadline approaches - filing earlier is cheaper. If you're netting enough that an S-corp election is on the table, that's the point where a CPA beats any of the above on ROI. Sources: - [FreeTaxUSA Review 2026 - The College Investor](https://thecollegeinvestor.com/20918/freetaxusa-review/) - [Cash App Taxes Review 2026 - The College Investor](https://thecollegeinvestor.com/39045/cash-app-taxes-review/) - [Keeper Tax Review - The College Investor](https://thecollegeinvestor.com/35362/keeper-tax-review/) - [Keeper Tax Review 2026 - FinanceBuzz](https://financebuzz.com/keeper-tax-review) - [TurboTax vs H&R Block vs FreeTaxUSA - WalletGrower](https://walletgrower.com/compare/turbotax-vs-hr-block-vs-freetaxusa) - [Tax Software for Small Business - iFeeltech](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa) - [7 Best Tax Software for Self-Employed in 2026 - unlike.net](https://unlike.net/best-tax-software-self-employed-2026/) - [TurboTax Self-Employed Review - Quarterly1099](https://quarterly1099.com/articles/turbotax-self-employed-review.html) - [Self-Employment Tax: 2026 Rates - NerdWallet](https://www.nerdwallet.com/taxes/learn/self-employment-tax)

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