What does AI recommend for tax preparation software (freelancers)? Checked 2026-09-08

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-08

Coverage: Claude (Anthropic) with web search. Other engines not included.

The question asked, verbatim: best tax preparation software for freelancers. This page records one answer on one date. It is a measurement, not a ranking and not a recommendation.

Brands named, in the order the engine gave

1. FreeTaxUSA recommended
   FreeTaxUSA - my default recommendation for most freelancers.
2. multi-state mentioned
   It also supports multi-state and prior-year returns, which the truly free options don't.
3. Cash App Taxes mentioned
   Cash App Taxes - if you want $0 total, federal and state.
4. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - the value pick with real hand-holding.
5. Self Visa mentioned
   TaxSlayer Self-Employed - the value pick with real hand-holding.
6. H&R Block compared
   Cheaper than H&R Block or TurboTax while still giving guided Schedule C prep, deduction prompts, quarterly-estimate help, and access to a tax pro.
7. Good Grants mentioned
   Good middle ground if FreeTaxUSA's bare interface makes you nervous but TurboTax's price makes you angrier.
8. H&R Block Self-Employed mentioned
   H&R Block Self-Employed - best if you want a human you can sit across from.
9. TurboTax Premium mentioned
   TurboTax Premium - the best guided experience, and priced like it.
10. Uber Eats mentioned
    It genuinely is the smoothest walkthrough of vehicle expenses, home office, depreciation, and QBI, and it imports from QuickBooks/Uber/etc.
11. S-corp mentioned
    I'd only pay the premium if your return is messy - inventory, an S-corp election, big asset purchases - or if you value the interview enough to fund it.
12. Keeper mentioned
    Keeper - the one built specifically for freelancers, not adapted for them.
13. January 31 mentioned
    The value here isn't the filing engine, it's catching write-offs in March that you'd have forgotten by next January.

Sources the engine cited

The answer, as recorded

## My short list **1. FreeTaxUSA - my default recommendation for most freelancers.** Schedule C, SE tax, home office, QBI, and 1099-NEC/1099-K income are all in the free federal tier; you only pay ~$15-16 per state. It's a plain, form-driven interview with no upsell theater. If your freelance situation is "several clients, some expenses, one state," this does the whole job for the price of a lunch. It also supports multi-state and prior-year returns, which the truly free options don't. **2. Cash App Taxes - if you want $0 total, federal *and* state.** Genuinely free with no tiers, no income cap, and it handles Schedule C. The catch is real, though: no multi-state, no part-year or nonresident state returns, and a few niche forms are missing. Great for a single-state freelancer with a straightforward return; a dead end the year you move or pick up out-of-state work. ([Forbes review](https://www.forbes.com/advisor/taxes/cash-app-taxes-review/)) **3. TaxSlayer Self-Employed - the value pick with real hand-holding.** Cheaper than H&R Block or TurboTax while still giving guided Schedule C prep, deduction prompts, quarterly-estimate help, and access to a tax pro. Good middle ground if FreeTaxUSA's bare interface makes you nervous but TurboTax's price makes you angrier. **4. H&R Block Self-Employed - best if you want a human you can sit across from.** Roughly $85-$115 federal, typically 20-30% under the comparable TurboTax tier, and you can escalate to a virtual or in-person pro mid-return. Worth it if this is your first year with 1099 income and you want a safety net. ([comparison](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa)) **5. TurboTax Premium - the best guided experience, and priced like it.** ~$129 federal plus state. It genuinely is the smoothest walkthrough of vehicle expenses, home office, depreciation, and QBI, and it imports from QuickBooks/Uber/etc. I'd only pay the premium if your return is messy - inventory, an S-corp election, big asset purchases - or if you value the interview enough to fund it. **6. Keeper - the one built specifically for freelancers, not adapted for them.** It links to your bank/cards and auto-classifies deductible expenses year-round, then files with a tax pro reviewing. ~$99/yr filing only, ~$199 bundled with tracking, ~$399 for quarterly-estimate help and audit support. The value here isn't the filing engine, it's catching write-offs in March that you'd have forgotten by next January. Watch for the auto-renewal. ([College Investor review](https://thecollegeinvestor.com/35362/keeper-tax-review/), [FinanceBuzz](https://financebuzz.com/keeper-tax-review)) ## How I'd actually choose Start with **FreeTaxUSA**. If you'd rather pay nothing at all and file in one state, **Cash App Taxes**. If your bookkeeping is a shoebox of transactions, **Keeper** for the year and file through it. Pay up for **TurboTax Premium** only when the return is genuinely complicated. One thing none of these fully solve: quarterly estimated payments. Most only help you after the fact. If you're newly freelancing, set aside ~25-30% of net income and pay quarterly via IRS Direct Pay regardless of which software you pick - the underpayment penalty is the most common avoidable cost for new freelancers. A caveat on the numbers: prices shift every filing season and several of the figures above come from review roundups rather than the vendors. Confirm current pricing on the provider's own site before you commit, since some tiers jump in price close to the April deadline. Sources: - [Cash App Taxes Review - Forbes Advisor](https://www.forbes.com/advisor/taxes/cash-app-taxes-review/) - [Keeper Tax Review - The College Investor](https://thecollegeinvestor.com/35362/keeper-tax-review/) - [Keeper Tax Review - FinanceBuzz](https://financebuzz.com/keeper-tax-review) - [Tax Software for Small Business: TurboTax vs H&R Block vs FreeTaxUSA - iFeeltech](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-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) - [7 Best Tax Software for Self-Employed in 2026 - unlike.net](https://unlike.net/best-tax-software-self-employed-2026/)

Recorded 2026-09-08 through Claude (Anthropic) with web search, model claude-opus-5. Permanent address: /answers/s/tax-preparation-software-freelancers-2026-09-08

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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.