What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-23

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-23

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
   TurboTax Premium - if your situation is messy or you want hand-holding.
3. TurboTax Premium mentioned
   TurboTax Premium - if your situation is messy or you want hand-holding.
4. QuickBooks mentioned
   Best deduction-discovery interview in the business, best import (brokerages, payment platforms, QuickBooks), and the Live Assisted/Full Service options put a CPA on 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 - cheapest paid tier with real support.
8. Cash App Taxes mentioned
   Cash App Taxes - free including state, but with caveats.
9. TaxAct Entrepreneur mentioned
   TaxAct Entrepreneur - I'd only reach for this if the others don't fit;
10. QuickBooks Self-Employed mentioned
    Pair whatever you pick with year-round expense tracking (QuickBooks Self-Employed, Wave, or a spreadsheet) - clean books make any of these tools equivalent.
11. Wave mentioned
    Pair whatever you pick with year-round expense tracking (QuickBooks Self-Employed, Wave, or a spreadsheet) - clean books make any of these tools equivalent.

Sources the engine cited

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The answer, as recorded

Here's who I'd actually name, in order: **1. FreeTaxUSA - my default recommendation for most freelancers.** It handles Schedule C, 1099-NEC income, home office, mileage, and self-employment tax on the free federal tier; state is ~$16. Same calculations as the expensive tiers, and the Deluxe add-on (~$8) gets you audit assist and priority support. If your freelance taxes are "a few 1099s and a pile of deductions," this is the one. The UI is plain and it's weaker on importing forms automatically - you'll type more. ([FreeTaxUSA comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)) **2. TurboTax Premium - if your situation is messy or you want hand-holding.** Best deduction-discovery interview in the business, best import (brokerages, payment platforms, QuickBooks), and the Live Assisted/Full Service options put a CPA on it. Worth it specifically if you have multiple income streams, crypto/stock sales alongside freelance income, a vehicle + home office, or you're filing self-employed for the first time and want the software to ask the right questions. It's the most expensive by a wide margin - roughly $130-160 federal plus ~$60+ per state. ([TurboTax pricing](https://www.techrepublic.com/article/turbotax-vs-hr-block/)) **3. H&R Block Self-Employed - the sensible middle.** Comparable Schedule C coverage to TurboTax at ~$130 federal + ~$49 state, decent import, and the real differentiator: physical offices, so you can escalate to a human in person if something goes wrong. Good pick if you want a brand-name safety net but TurboTax's pricing annoys you. ([H&R Block](https://www.techrepublic.com/article/turbotax-vs-hr-block/)) **4. TaxSlayer Self-Employed - cheapest paid tier with real support.** ~$75 federal + ~$48 state, includes self-employed-specific guidance and tax pro access. Sits between FreeTaxUSA and H&R Block on both price and polish. ([TaxSlayer](https://investormint.com/small-business/best-tax-software-self-employed-2026)) **5. Cash App Taxes - free including state, but with caveats.** Genuinely $0 federal *and* state with Schedule C support. The catch: no multi-state filing, no part-year returns, no foreign income, and support is thin. Fine for a single-state freelancer with a simple return who wants to pay nothing. ([comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)) **6. TaxAct Entrepreneur** - I'd only reach for this if the others don't fit; it's priced near H&R Block with weaker import. ([TaxAct](https://investormint.com/small-business/best-tax-software-self-employed-2026)) Two things that matter more than the software choice: - **Quarterly estimated taxes.** All the self-employed tiers generate 1040-ES vouchers, but none of them will remind you in June. If you're newly freelance, that's the thing that actually bites. Pair whatever you pick with year-round expense tracking (QuickBooks Self-Employed, Wave, or a spreadsheet) - clean books make any of these tools equivalent. - **Over roughly $75-100k of self-employment income, or if you're considering an S-corp election,** skip DIY and hire a CPA or EA. The entity-structure and retirement-plan decisions (solo 401(k) vs. SEP-IRA) are worth multiples of the prep fee, and no software will raise them with you. One caveat on the numbers: the prices above are 2025-tax-year figures as reported mid-2026. Vendors re-price every January and discount early-season, so confirm on the vendor's own page before you commit.

Near this answer

The same question, recorded on other dates: 2026-10-21, 2026-10-19, 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.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-23), nonprofits (asked 2026-10-23).

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

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