What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-11
Claude (Anthropic) with web search claude-opus-5 asked 2026-10-11
On 2026-10-11, Claude (Anthropic) with web search was asked "best tax preparation software for freelancers". It named 8 brands, in this order: FreeTaxUSA, Cash App Taxes, TurboTax, TurboTax Premium, H&R Block, H&R Block Self-Employed, TaxSlayer Self-Employed and Keeper.
| Question | best tax preparation software for freelancers |
|---|---|
| Asked on | 2026-10-11 |
| Engine | Claude (Anthropic) with web search |
| Model | claude-opus-5 |
| Brands named | 8 |
| Sources cited | 6 |
| Audience | freelancers |
| Coverage | Coverage: Claude (Anthropic) with web search. Other engines not included. |
| Last verified |
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
- FreeTaxUSA recommended
FreeTaxUSA - my default pick for most freelancers.
- Cash App Taxes recommended
Cash App Taxes - if you want it completely free, federal and state, with no income cap.
- TurboTax recommended
TurboTax Premium (Self-Employed) - the most expensive option (roughly $119-$159 federal plus ~$60/state, more for Live Assisted) and worth it mainly for two things: the best 1099/bank/Uber-Lyft-style data imports, and the strongest deduction interview if you genuinely don't know what's deductible.
- TurboTax Premium recommended
TurboTax Premium (Self-Employed) - the most expensive option (roughly $119-$159 federal plus ~$60/state, more for Live Assisted) and worth it mainly for two things: the best 1099/bank/Uber-Lyft-style data imports, and the strongest deduction interview if you genuinely don't know what's deductible.
- H&R Block recommended
H&R Block Self-Employed - the sensible middle.
- H&R Block Self-Employed recommended
H&R Block Self-Employed - the sensible middle.
- TaxSlayer Self-Employed recommended
TaxSlayer Self-Employed - the value play when your return isn't simple but you refuse to pay premium-brand prices.
- Keeper recommended
Keeper - different category, and the one I'd add if your real problem is bookkeeping, not filing.
What Claude (Anthropic) with web search answered about tax preparation software for freelancers on 2026-10-11: 8 brands named, 6 sources cited. This question is asked again on the nightly schedule and each new answer gets its own dated page.
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Cited sources with a record here: primewayfcu.com, beancount.io, techradar.com. The owner of a cited domain can take an email for each new citation.
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Sources the engine cited
| Source | Type |
|---|---|
| investormint.com | other |
| primewayfcu.com | other |
| supermoney.com | other |
| beancount.io | other |
| finder.com | other |
| techradar.com | review |
The answer, as recorded
For a freelancer with a Schedule C, here's what I'd actually recommend, in order: **1. FreeTaxUSA** - my default pick for most freelancers. Federal filing is free at every complexity level including Schedule C, 1099-NEC, home office, and depreciation, with state around $15-16. It's a real IRS-authorized e-file provider, not a stripped-down "simple returns only" tier, so you're not paying $150+ for forms that cost the software nothing. Downside: you categorize your own expenses, and live help is a paid add-on. **2. Cash App Taxes** - if you want it completely free, federal *and* state, with no income cap. It covers Schedule C, 1099-NEC, crypto, and rentals at $0. The tradeoffs are real: no live support, no multi-state returns, and it's weak at walking you through depreciation or a first-year business. Best for a straightforward one-state freelance return. **3. TurboTax Premium (Self-Employed)** - the most expensive option (roughly $119-$159 federal plus ~$60/state, more for Live Assisted) and worth it mainly for two things: the best 1099/bank/Uber-Lyft-style data imports, and the strongest deduction interview if you genuinely don't know what's deductible. If you've filed with them before, the year-over-year carryforward also saves real time. **4. H&R Block Self-Employed** - the sensible middle. Comparable Schedule C coverage to TurboTax at a lower price, and the one differentiator nobody else has: ~12,000 physical offices, so if the return goes sideways you can hand it to a human in person. **5. TaxSlayer Self-Employed** - the value play when your return isn't simple but you refuse to pay premium-brand prices. Flat, cheap pricing that doesn't scale with how complicated you are. Import tools are mediocre, so expect manual entry. **6. Keeper** - different category, and the one I'd add if your real problem is *bookkeeping*, not filing. ~$20/month or $192/year; it auto-scans linked accounts for deductions all year, estimates quarterlies, and the annual plan includes filing with a return reviewed and signed by an in-house tax pro. Good for people who get to April with a shoebox of mixed personal/business charges. **My short version:** FreeTaxUSA if you know your numbers, Keeper if you don't track expenses all year, TurboTax only if import convenience is worth ~$200 to you. And regardless of software: set up quarterly estimated payments, because the penalty surprise hurts more than any filing fee. Sources: - [Best tax software self-employed 2026 - InvestorMint](https://investormint.com/small-business/best-tax-software-self-employed-2026) - [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) - [TurboTax vs FreeTaxUSA - SuperMoney](https://www.supermoney.com/turbotax-vs-freetaxusa) - [IRS Direct File 2026 free filing alternatives guide - Beancount](https://beancount.io/blog/2026/07/12/irs-direct-file-2026-free-tax-filing-alternatives-guide) - [Keeper review - Finder](https://www.finder.com/best-tax-software/keeper-tax) - [Keeper Tax review - TechRadar](https://www.techradar.com/reviews/keeper-tax) One caveat: the exact prices above came from comparison write-ups that disagreed with each other by $20-40 on several tiers, so treat them as ballpark and confirm on the vendor's own checkout page - these companies also raise prices as April approaches.
Near this answer
The same question, recorded on other dates: 2026-10-08, 2026-10-06, 2026-10-03, 2026-10-01, 2026-09-29, 2026-09-27, 2026-09-25, 2026-09-23, 2026-09-21, 2026-09-16, 2026-09-14.
tax preparation software, asked for other audiences: small businesses (asked 2026-10-11), nonprofits (asked 2026-10-11).
Other categories with a recorded answer: accounting software, accounts payable automation, audit management software, bookkeeping services.
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Answer Watch records what one AI answer engine said on one date, nothing more. Each page names the engine and the model, carries the date the question was asked, and lists the brands that appeared in the answer in the order the engine gave them, with the sources it cited. It is a measurement, not a ranking, not a recommendation and not a claim about the world. Brands that did not appear in an answer are not named on any public page. Coverage: Claude (Anthropic) with web search. Other engines not included.