What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-26

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-26

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 pick for most freelancers.
2. TurboTax compared
   The interface is plain and dated, but it handles self-employment correctly and you'll save $100+ versus TurboTax for the same return.
3. H&R Block recommended
   H&R Block Self-Employed - The one I'd name if you want hand-holding without TurboTax prices.
4. H&R Block Self-Employed recommended
   H&R Block Self-Employed - The one I'd name if you want hand-holding without TurboTax prices.
5. TurboTax Premium recommended
   TurboTax Premium - Expensive (~$119-159 federal + state) and aggressive about upsells, but genuinely the best at two things: finding deductions you didn't know to claim, and importing data directly from Uber/Lyft/DoorDash/Square/brokerages.
6. DoorDash recommended
   TurboTax Premium - Expensive (~$119-159 federal + state) and aggressive about upsells, but genuinely the best at two things: finding deductions you didn't know to claim, and importing data directly from Uber/Lyft/DoorDash/Square/brokerages.
7. Square recommended
   TurboTax Premium - Expensive (~$119-159 federal + state) and aggressive about upsells, but genuinely the best at two things: finding deductions you didn't know to claim, and importing data directly from Uber/Lyft/DoorDash/Square/brokerages.
8. TaxSlayer Self-Employed recommended
   TaxSlayer Self-Employed - The value middle ground.
9. TaxAct Self-Employed recommended
   TaxAct Self-Employed - Transparent pricing, solid Schedule C, but weak import tools mean a lot of manual entry.
10. QuickBooks mentioned
    Two things worth knowing beyond the software: if your freelance income is meaningful, pair whichever you pick with real bookkeeping during the year (QuickBooks Self-Employed or Wave) - tax software is only as good as your records.
11. QuickBooks Self-Employed mentioned
    Two things worth knowing beyond the software: if your freelance income is meaningful, pair whichever you pick with real bookkeeping during the year (QuickBooks Self-Employed or Wave) - tax software is only as good as your records.
12. Wave mentioned
    Two things worth knowing beyond the software: if your freelance income is meaningful, pair whichever you pick with real bookkeeping during the year (QuickBooks Self-Employed or Wave) - tax software is only as good as your records.
13. Cash App Taxes compared
    - TurboTax vs H&R Block vs TaxAct vs TaxSlayer vs FreeTaxUSA vs Cash App Taxes - PrimeWay FCU (https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)

Sources the engine cited

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The answer, as recorded

Here's what I'd actually recommend, in order: **1. FreeTaxUSA** - My default pick for most freelancers. Federal filing is $0 *including* Schedule C, 1099-NEC income, home office, and depreciation - the stuff other vendors paywall. State is ~$16. The interface is plain and dated, but it handles self-employment correctly and you'll save $100+ versus TurboTax for the same return. If your freelance taxes are "a few 1099s and some deductions," start here. **2. H&R Block Self-Employed** - The one I'd name if you want hand-holding without TurboTax prices. Roughly $85-125 federal plus ~$37/state, comparable Schedule C coverage and deduction guidance, better import support than the budget tools. The real differentiator: ~9,000 physical offices, so you can hand off or get a human review mid-return. Good if this is your first year self-employed and you're nervous. **3. TurboTax Premium** - Expensive (~$119-159 federal + state) and aggressive about upsells, but genuinely the best at two things: finding deductions you didn't know to claim, and importing data directly from Uber/Lyft/DoorDash/Square/brokerages. Worth it if you have multiple income streams, vehicle *and* home office deductions, or you'd rather pay $150 than spend an evening on data entry. **4. TaxSlayer Self-Employed** - The value middle ground. Cheaper than the big two, built specifically for contractors and side-hustlers, includes some tax-pro support. Choose it over FreeTaxUSA if you want a nicer interface and a support line. **5. TaxAct Self-Employed** - Transparent pricing, solid Schedule C, but weak import tools mean a lot of manual entry. I'd only pick it over the above if you've used it before and like it. Two things worth knowing beyond the software: if your freelance income is meaningful, pair whichever you pick with real bookkeeping during the year (QuickBooks Self-Employed or Wave) - tax software is only as good as your records. And once you're past roughly $75-100k of self-employment income or considering an S-corp election, a CPA usually pays for themselves versus any of these. Caveat on the numbers: tax software pricing shifts through filing season and typically rises closer to the April deadline, so treat the dollar figures as approximate and check the current price before you file. Sources: - [FreeTaxUSA vs TurboTax comparison - SuperMoney](https://www.supermoney.com/turbotax-vs-freetaxusa) - [TurboTax vs H&R Block vs TaxAct vs TaxSlayer vs FreeTaxUSA vs Cash App Taxes - PrimeWay FCU](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 H&R Block - TechRepublic](https://www.techrepublic.com/article/turbotax-vs-hr-block/) - [Best tax software of 2026 - TechRadar](https://www.techradar.com/best/best-tax-software)

Near this answer

The same question, recorded on other dates: 2026-10-23, 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.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-26), nonprofits (asked 2026-10-26).

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

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