What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-21

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-21

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 mentioned
   Short answer: FreeTaxUSA for most freelancers, TurboTax Premium if you want hand-holding
2. TurboTax mentioned
   Short answer: FreeTaxUSA for most freelancers, TurboTax Premium if you want hand-holding
3. TurboTax Premium mentioned
   Short answer: FreeTaxUSA for most freelancers, TurboTax Premium if you want hand-holding
4. Square mentioned
   Best deduction interview in the business, imports from Uber/Lyft/Square/QuickBooks, and it calculates next year's quarterly estimates for you.
5. QuickBooks mentioned
   Best deduction interview in the business, imports from Uber/Lyft/Square/QuickBooks, and it calculates next year's quarterly estimates for you.
6. H&R Block mentioned
   H&R Block Self-Employed (https://www.tomsguide.com/face-off/turbotax-vs-hrblock) - the middle option, and the one with a storefront.
7. H&R Block Self-Employed mentioned
   H&R Block Self-Employed (https://www.tomsguide.com/face-off/turbotax-vs-hrblock) - the middle option, and the one with a storefront.
8. Cash App Taxes mentioned
   Cash App Taxes (https://www.forbes.com/sites/kellyphillipserb/2026/01/06/direct-file-is-gone-heres-how-you-can-still-file-your-taxes-for-free/) - $0 federal and $0 state, Schedule C included.
9. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed (https://thecollegeinvestor.com/23970/hr-block-alternatives/) - cheap paid middle ground, typically well under the big two, and it includes some tax-pro question access.
10. QuickBooks Solopreneur mentioned
    QuickBooks Solopreneur (formerly Self-Employed) + a real CPA - for freelancers past roughly $100K, with an S-corp, multi-state work, or inventory.

Sources the engine cited

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The answer, as recorded

## Short answer: FreeTaxUSA for most freelancers, TurboTax Premium if you want hand-holding **1. [FreeTaxUSA](https://www.business.org/finance/taxes/freetaxusa-review/) - what I'd use.** Federal is $0 *including* Schedule C, Schedule SE, home office, depreciation, and 1099-NEC/K income - the stuff every other company treats as premium. State is ~$15.99. The interface is plainer than TurboTax's, but the forms coverage is essentially complete. For a freelancer with a few 1099s and a pile of expenses, you're filing for under $20 instead of $200. **2. [TurboTax Premium](https://www.nerdwallet.com/taxes/learn/hr-block-vs-turbotax) (the old "Self-Employed" tier) - if you'd rather pay to be walked through it.** Best deduction interview in the business, imports from Uber/Lyft/Square/QuickBooks, and it calculates next year's quarterly estimates for you. Downside is price: roughly $129-$159 federal plus ~$59-$64 per state, and it climbs as April approaches. Worth it mainly for your first self-employed year or if your return is genuinely messy. **3. [H&R Block Self-Employed](https://www.tomsguide.com/face-off/turbotax-vs-hrblock) - the middle option, and the one with a storefront.** About $85-$120 federal plus ~$37-$49 state, so meaningfully cheaper than TurboTax for a similar guided experience, and you can hand it to a human at a physical office if you get stuck. Good pick if you want DIY with an escape hatch. **4. [Cash App Taxes](https://www.forbes.com/sites/kellyphillipserb/2026/01/06/direct-file-is-gone-heres-how-you-can-still-file-your-taxes-for-free/) - $0 federal *and* $0 state, Schedule C included.** Genuinely free with no upsell, which nothing else on this list matches. Caveats: mobile-first, one state only, no multi-state or part-year returns, and it can't handle a few niche forms. If your situation fits, it's free money. **5. [TaxSlayer Self-Employed](https://thecollegeinvestor.com/23970/hr-block-alternatives/) - cheap paid middle ground**, typically well under the big two, and it includes some tax-pro question access. Fewer integrations and a less polished deduction finder; I'd take FreeTaxUSA over it on value, but it's a fine alternative. **6. [Keeper](https://www.keepertax.com/switch-from/turbotax) - if your actual problem is untracked expenses, not filing.** ~$20/month or $192/year; it links your bank, flags business purchases year-round via AI plus a human bookkeeper, then lets you file from the app on the annual plan. The filing engine is weaker than the others, but if you show up each April with no records, the tracking pays for itself. **7. QuickBooks Solopreneur (formerly Self-Employed) + a real CPA** - for freelancers past roughly $100K, with an S-corp, multi-state work, or inventory. At that point the bookkeeping-to-return pipeline and a human's judgment on entity structure beat any DIY box. **One important change this year:** IRS Direct File is [dead](https://www.kiplinger.com/taxes/a-free-tax-filing-option-just-disappeared) - the IRS killed it in November 2025 and it did not run for the 2026 season. It never supported Schedule C anyway, so freelancers lose little, but don't go looking for it. [IRS Free File](https://www.forbes.com/sites/kellyphillipserb/2026/01/06/direct-file-is-gone-heres-how-you-can-still-file-your-taxes-for-free/) still exists through partner companies if your AGI is under the threshold (~$84K). Two things no software does for you: pay your **quarterly estimates** (next deadline is Jan 15, 2027 for Q4 2026 - the software calculates them, you still have to send them via IRS Direct Pay), and remember that your **self-employment tax** is ~15.3% on top of income tax, half of which is deductible. Pricing above moves constantly and tends to surge near the April deadline, so check the current number before you commit. **Sources:** - [NerdWallet: TurboTax vs. H&R Block](https://www.nerdwallet.com/taxes/learn/hr-block-vs-turbotax) - [Tom's Guide: H&R Block vs. TurboTax](https://www.tomsguide.com/face-off/turbotax-vs-hrblock) - [business.org: FreeTaxUSA Review](https://www.business.org/finance/taxes/freetaxusa-review/) - [Forbes: Direct File Is Gone - How to Still File Free](https://www.forbes.com/sites/kellyphillipserb/2026/01/06/direct-file-is-gone-heres-how-you-can-still-file-your-taxes-for-free/) - [Kiplinger: A Free Tax Filing Option Has Disappeared for 2026](https://www.kiplinger.com/taxes/a-free-tax-filing-option-just-disappeared) - [Tax Notes: IRS Shutters Direct File](https://www.taxnotes.com/featured-news/irs-shutters-direct-file-citing-cost-and-low-uptake/2025/11/05/7t7q0) - [Keeper: vs. TurboTax](https://www.keepertax.com/switch-from/turbotax) · [finder: Keeper review](https://www.finder.com/best-tax-software/keeper-tax) - [The College Investor: H&R Block alternatives](https://thecollegeinvestor.com/23970/hr-block-alternatives/)

Near this answer

The same question, recorded on other dates: 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, 2026-09-27.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-21), nonprofits (asked 2026-10-21).

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

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