What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-18

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-18

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. TurboTax mentioned
   The interview is less hand-holdy than TurboTax, but it does everything a single-person freelance business needs, and it won't try to upsell you mid-return.
3. Cash App Taxes mentioned
   Cash App Taxes - the other genuinely free option, including Schedule C, with free state filing too.
4. TurboTax Premium mentioned
   TurboTax Premium - worth the money only in specific cases: your first year self-employed and you want the deduction-by-deduction interview, you have messy multiple income streams plus investments or rentals, or you want Live Assisted/Full Service to have a CPA review or file it.
5. H&R Block mentioned
   H&R Block Self-Employed - the sensible middle.
6. H&R Block Self-Employed mentioned
   H&R Block Self-Employed - the sensible middle.
7. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - the value pick if you want a paid, guided product cheaply.
8. TaxAct mentioned
   TaxAct - only if you've used it before and like it.
9. Wave mentioned
   Two things that matter more than the software choice: keep bookkeeping separate during the year (Wave, QuickBooks Solopreneur, or just a clean spreadsheet) - tax software is bad at reconstructing a year of expenses in April - and make your quarterly estimated payments directly through IRS Direct Pay
10. QuickBooks mentioned
    Two things that matter more than the software choice: keep bookkeeping separate during the year (Wave, QuickBooks Solopreneur, or just a clean spreadsheet) - tax software is bad at reconstructing a year of expenses in April - and make your quarterly estimated payments directly through IRS Direct Pay
11. QuickBooks Solopreneur mentioned
    Two things that matter more than the software choice: keep bookkeeping separate during the year (Wave, QuickBooks Solopreneur, or just a clean spreadsheet) - tax software is bad at reconstructing a year of expenses in April - and make your quarterly estimated payments directly through IRS Direct Pay

Sources the engine cited

The answer, as recorded

**FreeTaxUSA** - my default recommendation for most freelancers. Schedule C, 1099-NEC income, home office, and SE tax are all included in the $0 federal tier; you only pay ~$16 per state return. The interview is less hand-holdy than TurboTax, but it does everything a single-person freelance business needs, and it won't try to upsell you mid-return. ([FreeTaxUSA review](https://fitsmallbusiness.com/freetaxusa-review), [pricing comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)) **Cash App Taxes** - the other genuinely free option, including Schedule C, with free state filing too. Worth trying first if your return is simple. Caveats: no multi-state filing, no part-year/nonresident state returns, and you must file on their app/web flow with no expert help available. If you hit one of those limits, fall back to FreeTaxUSA. **TurboTax Premium** - worth the money only in specific cases: your first year self-employed and you want the deduction-by-deduction interview, you have messy multiple income streams plus investments or rentals, or you want Live Assisted/Full Service to have a CPA review or file it. Expect roughly $129-$159 federal plus $40-$64 per state, and the Live tiers land north of $200. It's the best UX in the category and also the most aggressive about mid-session upgrades. ([InvestorMint](https://investormint.com/small-business/best-tax-software-self-employed-2026)) **H&R Block Self-Employed** - the sensible middle. Comparable Schedule C coverage at a lower price (roughly $85 federal + ~$37/state), and the real differentiator is that you can hand off to a human at a physical office if the return gets away from you. Good if you want TurboTax-style guidance without TurboTax pricing. **TaxSlayer Self-Employed** - the value pick if you want a paid, guided product cheaply. Flat, low pricing with self-employment support and some tax-pro access; the interface is dated and imports are weaker than the big two. **TaxAct** - only if you've used it before and like it. Fine Schedule C support, but it no longer undercuts the field on price enough to beat FreeTaxUSA, and import capabilities are limited. Two things that matter more than the software choice: keep bookkeeping separate during the year (Wave, QuickBooks Solopreneur, or just a clean spreadsheet) - tax software is bad at reconstructing a year of expenses in April - and make your quarterly estimated payments directly through IRS Direct Pay rather than paying for a tool to do it. A note on the prices above: they move around a lot by season and source, so treat them as approximate and check the current page before you commit. Sources: - [FreeTaxUSA review - Fit Small Business](https://fitsmallbusiness.com/freetaxusa-review) - [TurboTax vs H&R Block vs TaxAct vs TaxSlayer vs FreeTaxUSA 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) - [TurboTax vs FreeTaxUSA - SuperMoney](https://www.supermoney.com/turbotax-vs-freetaxusa)

Near this answer

The same question, recorded on other dates: 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, 2026-09-23.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-18), nonprofits (asked 2026-10-18).

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

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