What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-01

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-01

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 - What I'd recommend to most freelancers.
2. TurboTax mentioned
   It's an authorized IRS e-file provider and the math is the math - a Schedule C filled out correctly here produces the identical return TurboTax would.
3. H&R Block mentioned
   H&R Block Self-Employed - The best balance if you want real guidance without TurboTax pricing.
4. H&R Block Self-Employed mentioned
   H&R Block Self-Employed - The best balance if you want real guidance without TurboTax pricing.
5. TurboTax Premium mentioned
   TurboTax Premium (formerly Self-Employed) - The most polished Schedule C walkthrough there is, and worth paying for exactly once: your first self-employed year, or a year with something genuinely weird (crypto income, a business sold, big asset depreciation).
6. TaxSlayer Self-Employed recommended
   TaxSlayer Self-Employed - My pick if you want more guidance than FreeTaxUSA at a price much closer to it than to TurboTax.
7. Cash App Taxes mentioned
   Cash App Taxes - Free federal and free state, which nothing else on this list offers, and it does handle Schedule C.
8. Keeper mentioned
   Keeper - Not a replacement for the above so much as the thing that makes them work.
9. QuickBooks Solopreneur mentioned
   Worth naming separately: QuickBooks Solopreneur/Self-Employed if you want bookkeeping, mileage, and quarterly estimates handled all year with a clean export into TurboTax.
10. QuickBooks Solopreneur/Self-Employed mentioned
    Worth naming separately: QuickBooks Solopreneur/Self-Employed if you want bookkeeping, mileage, and quarterly estimates handled all year with a clean export into TurboTax.

Sources the engine cited

The answer, as recorded

## My actual picks, in order **1. FreeTaxUSA** - What I'd recommend to most freelancers. Schedule C, SE tax, 1099-NEC, home office, and quarterly-estimate worksheets are all in the free federal tier; you only pay per state (roughly $15). It's an authorized IRS e-file provider and the math is the math - a Schedule C filled out correctly here produces the identical return TurboTax would. The interface is plain and the interview is less hand-holding, so it rewards knowing roughly what your deductions are. **2. H&R Block Self-Employed** - The best balance if you want real guidance without TurboTax pricing. Solid Schedule C interview, good expense-category prompts, imports 1099s, and it's the only one on this list where you can walk into a physical office and hand your mess to a human if the return gets complicated (multi-state, an S-corp election, a sloppy first year). **3. TurboTax Premium (formerly Self-Employed)** - The most polished Schedule C walkthrough there is, and worth paying for exactly once: your first self-employed year, or a year with something genuinely weird (crypto income, a business sold, big asset depreciation). It asks industry-specific deduction questions others skip. It's also the most expensive by a wide margin and the most aggressive about upselling you to "Live" review mid-filing. **4. TaxSlayer Self-Employed** - My pick if you want more guidance than FreeTaxUSA at a price much closer to it than to TurboTax. Flat, predictable pricing and included tax-pro Q&A. Less slick, totally competent. **5. Cash App Taxes** - Free federal *and* free state, which nothing else on this list offers, and it does handle Schedule C. Caveats are real: no multi-state returns, no foreign income, no part-year-resident filings, and almost no guidance. Great for a simple single-state 1099 return; a dead end the moment your situation isn't simple. **6. Keeper** - Not a replacement for the above so much as the thing that makes them work. It's a year-round deduction tracker that watches your bank/card feeds and flags business expenses as they happen, then files. If your real problem is "I have no idea what I spent," this is the fix - the filing software was never the bottleneck. **Worth naming separately:** **QuickBooks Solopreneur/Self-Employed** if you want bookkeeping, mileage, and quarterly estimates handled all year with a clean export into TurboTax. And if your freelance income cleared roughly $75-100k, or you're weighing an S-corp election, a **flat-fee CPA or enrolled agent** (often $400-800 for a Schedule C return) will usually save more than the software costs - software can't advise you on entity structure. ## One caveat on the numbers I deliberately didn't quote hard prices above. The pages I pulled disagreed with each other substantially on TurboTax's self-employed tier - $129, $139, and $169 all appeared - and several were affiliate-driven listicles rather than tested reviews. The *ordering* of these products by cost is stable and reliable; the exact dollar figures move with the season (they rise as April approaches) and should be checked on each vendor's own site before you commit. Sources: - [Tax Prep Software Comparison: TurboTax vs FreeTaxUSA vs H&R Block](https://sharper.tax/learn/guides/tax-prep-software-comparison/) - [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 2026: TurboTax vs H&R Block vs FreeTaxUSA](https://taxo.com/best-tax-software-2026-comparison/) - [Best Tax Software for Self-Employed in 2026 - SmashingApps](https://www.smashingapps.com/best-tax-software-for-self-employed-in-2026/) - [Best tax software of 2026 - TechRadar](https://www.techradar.com/best/best-tax-software)

Near this answer

The same question, recorded on other dates: 2026-09-29, 2026-09-27, 2026-09-25, 2026-09-23, 2026-09-21, 2026-09-16, 2026-09-14, 2026-09-12, 2026-09-10, 2026-09-08.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-01), nonprofits (asked 2026-10-01).

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

Markdown edition · JSON record · the question page, with every recording · Answer Watch · AEO Watch

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.