What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-21

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-21

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 recommended
   FreeTaxUSA - my default recommendation for most freelancers.
2. TurboTax mentioned
   The interface is plainer than TurboTax's, but the tax math is identical, and if you already know roughly what your deductions are, you're paying $100+ elsewhere purely for hand-holding.
3. TurboTax Premium mentioned
   TurboTax Premium - worth the ~$129 federal (plus state) if it's your first year filing Schedule C, or if your situation is genuinely messy: multiple 1099s, inventory, a home office you're unsure how to allocate, crypto or brokerage activity on top.
4. H&R Block mentioned
   H&R Block Self-Employed - the middle option.
5. H&R Block Self-Employed mentioned
   H&R Block Self-Employed - the middle option.
6. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - cheapest of the "guided" paid tiers, usually well under H&R Block.
7. Cash App Taxes mentioned
   Cash App Taxes - free federal and free state, and it does handle Schedule C.
8. Keeper mentioned
   Keeper - worth a look if your real problem is expense tracking, not filing.
9. S-corp mentioned
   Entity structure (whether an S-corp election saves you money) and retirement vehicles like a solo 401(k) or SEP-IRA are decisions software will not make for you, and they dwarf the $0-vs-$129 software question.

Sources the engine cited

The answer, as recorded

**FreeTaxUSA** - my default recommendation for most freelancers. Schedule C, Schedule SE, home office, vehicle, and QBI are all in the free federal tier; you only pay for state (~$16). The interface is plainer than TurboTax's, but the tax math is identical, and if you already know roughly what your deductions are, you're paying $100+ elsewhere purely for hand-holding. **TurboTax Premium** - worth the ~$129 federal (plus state) if it's your first year filing Schedule C, or if your situation is genuinely messy: multiple 1099s, inventory, a home office you're unsure how to allocate, crypto or brokerage activity on top. Its interview does the best job of surfacing deductions you wouldn't think to claim. The downside is aggressive upsells and the highest price in the category. **H&R Block Self-Employed** - the middle option. Typically 20-30% cheaper than the comparable TurboTax tier with similar guidance quality, and the real differentiator is being able to hand the return to a human at a physical office if you get stuck. Good if you want TurboTax-style guidance without TurboTax pricing. **TaxSlayer Self-Employed** - cheapest of the "guided" paid tiers, usually well under H&R Block. Includes estimated-quarterly-payment support, which matters a lot for freelancers trying to avoid underpayment penalties. Interface is dated but competent. **Cash App Taxes** - free federal *and* free state, and it does handle Schedule C. The catch is no multi-state filing, no part-year-resident edge cases, and no paid support, so it fits simple single-state freelance returns and not much beyond that. **Keeper** - worth a look if your real problem is *expense tracking*, not filing. It links to your bank, flags deductible transactions year-round, then files. More expensive per return than FreeTaxUSA, but it solves the "I have no idea what I spent on business in March" problem that costs most freelancers more than the software fee. One thing worth saying regardless of which you pick: if you're netting enough that self-employment tax is a real number, run at least one year past a CPA or EA. Entity structure (whether an S-corp election saves you money) and retirement vehicles like a solo 401(k) or SEP-IRA are decisions software will not make for you, and they dwarf the $0-vs-$129 software question. Sources: - [NerdWallet - Best Tax Software of 2026](https://nerdwallet.com/taxes/learn/best-tax-software) - [PrimeWay FCU - 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) - [iFeeltech - Tax Software for Small Business: TurboTax vs H&R Block vs FreeTaxUSA](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa) - [TurboTax - Self-Employment Tax Hub](https://turbotax.intuit.com/personal-taxes/self-employment-taxes/) - [H&R Block - Self-Employed Online Tax Filing](https://www.hrblock.com/online-tax-filing/self-employed-online-tax-filing/) Prices above are list prices that shift during filing season and tend to rise as April approaches - verify before you buy.

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