What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-10-28

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-28

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
   FreeTaxUSA - what I'd tell most freelancers to use.
2. TaxSlayer mentioned
   TaxSlayer Self-Employed - the best middle ground.
3. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - the best middle ground.
4. TurboTax mentioned
   Choose this over FreeTaxUSA if you want hand-holding and phone support but refuse to pay TurboTax prices.
5. TurboTax Premium mentioned
   TurboTax Premium - only if your time is worth more than the money.
6. QuickBooks mentioned
   What you're buying is the smoothest interview, the best 1099/brokerage/platform imports, mileage and expense import from QuickBooks, and optional live CPA review.
7. H&R Block compared
   H&R Block Self-Employed - ~$125 federal + ~$49 state, so cheaper than TurboTax with comparable Schedule C coverage.
8. H&R Block Self-Employed compared
   H&R Block Self-Employed - ~$125 federal + ~$49 state, so cheaper than TurboTax with comparable Schedule C coverage.
9. IRS Free File mentioned
   If you think you may want to hand the return to a human mid-process, or you like having somewhere to go if the IRS writes to you, that's a genuine advantage.
10. Keeper mentioned
    Keeper - a different category, and worth it for a specific type of freelancer.
11. TaxAct mentioned
    TaxAct Self-Employed - ~$70 federal + ~$40 state.
12. TaxAct Self-Employed mentioned
    TaxAct Self-Employed - ~$70 federal + ~$40 state.

Sources the engine cited

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The answer, as recorded

## My actual recommendations, in order **1. FreeTaxUSA** - what I'd tell most freelancers to use. Schedule C, Schedule SE, home office, vehicle, depreciation, and QBI are all in the free federal tier; you only pay for state (~$15.99). There's no "self-employed upgrade" paywall, which is the whole trick the big brands run. The interface is plain but competent. Unless your return is genuinely complicated, this is the right answer and saves you ~$100+. **2. TaxSlayer Self-Employed** - the best middle ground. Roughly $53 federal + $40 state (~$93 all-in), and at that tier you get self-employed-specific guidance plus access to a tax pro. Forbes and The College Investor both land on it as the value pick for Schedule C filers. Choose this over FreeTaxUSA if you want hand-holding and phone support but refuse to pay TurboTax prices. **3. TurboTax Premium** - only if your time is worth more than the money. ~$139 federal + ~$39-64 state. What you're buying is the smoothest interview, the best 1099/brokerage/platform imports, mileage and expense import from QuickBooks, and optional live CPA review. It is the most polished self-employment experience and also the most expensive by a wide margin. **4. H&R Block Self-Employed** - ~$125 federal + ~$49 state, so cheaper than TurboTax with comparable Schedule C coverage. The real reason to pick it: physical offices. If you think you may want to hand the return to a human mid-process, or you like having somewhere to go if the IRS writes to you, that's a genuine advantage. **5. Keeper** - a different category, and worth it for a specific type of freelancer. ~$192-199/year, links to your business cards and accounts, auto-categorizes write-offs year-round, assigns a bookkeeper, estimates quarterlies, and then files for you. If your real problem is that you don't track expenses all year and you're reconstructing everything in April, the bookkeeping is the value and the filing is a bonus. If you already keep clean books, skip it - you're paying for a feature you don't need. (FlyFin is the direct competitor at a similar price; Keeper has the better review record.) **6. TaxAct Self-Employed** - ~$70 federal + ~$40 state. Fine, transparent pricing, but weaker imports and more manual entry than TaxSlayer at a higher price. I'd only name it if you're already a returning TaxAct user with prior-year data in the system. **7. IRS Free File** - check your eligibility before paying anyone. If your AGI is under the threshold (~$84K recently), you can file through a partner product for free, self-employment schedules included. Worth two minutes on irs.gov/freefile. **One non-software note:** if you've elected S-corp status, have employees, operate in multiple states, or own rental property alongside the freelancing, stop shopping for software and hire a CPA or EA. A few hundred dollars for a professional beats any of the above once there's an entity return involved. Two caveats: these prices are for the current filing season and all of these vendors raise prices as April approaches, so file early. And "free" tiers at TurboTax, H&R Block, and TaxAct never cover self-employment income - that's W-2-only, every year. Sources: - [Forbes Advisor - The Best Tax Software For The Self-Employed](https://www.forbes.com/advisor/taxes/best-tax-software-for-self-employed/) - [The College Investor - TurboTax vs. H&R Block vs. TaxAct vs. TaxSlayer Pricing](https://thecollegeinvestor.com/15201/comparing-prices-turbotax-hr-block-tax-act/) - [The College Investor - TaxSlayer Review 2026](https://thecollegeinvestor.com/20925/taxslayer-review/) - [The College Investor - Free Tax Software 2026](https://thecollegeinvestor.com/17356/free-tax-software/) - [Kiplinger - The Best Tax Prep Software For Every Tax Situation](https://www.kiplinger.com/personal-finance/the-best-tax-prep-software-for-every-tax-situation) - [Keeper vs. FlyFin pricing comparison](https://www.keepertax.com/switch-from/flyfin) - [MoneyCrashers - Keeper Tax Review](https://www.moneycrashers.com/keeper-tax-review/)

Near this answer

The same question, recorded on other dates: 2026-10-26, 2026-10-23, 2026-10-21, 2026-10-19, 2026-10-18, 2026-10-16, 2026-10-14, 2026-10-11, 2026-10-08, 2026-10-06, 2026-10-03.

tax preparation software, asked for other audiences: small businesses (asked 2026-10-28), nonprofits (asked 2026-10-28).

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

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