What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-25

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-25

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. TurboTax mentioned
   TurboTax Premium - Worth the ~$130 federal + ~$65/state only if your situation is genuinely messy (multiple 1099s, vehicle and home office, crypto, K-1s, a spouse with equity comp) or if you dread the process enough that a good interview flow is worth paying for.
3. TurboTax Premium mentioned
   TurboTax Premium - Worth the ~$130 federal + ~$65/state only if your situation is genuinely messy (multiple 1099s, vehicle and home office, crypto, K-1s, a spouse with equity comp) or if you dread the process enough that a good interview flow is worth paying for.
4. H&R Block mentioned
   H&R Block Self-Employed - The middle option: roughly $85 federal + $37/state, most of TurboTax's hand-holding for meaningfully less, plus real human support and physical offices if you want to escalate.
5. H&R Block Self-Employed mentioned
   H&R Block Self-Employed - The middle option: roughly $85 federal + $37/state, most of TurboTax's hand-holding for meaningfully less, plus real human support and physical offices if you want to escalate.
6. TaxSlayer Self-Employed mentioned
   TaxSlayer Self-Employed - Cheapest of the "guided" tier, usually under $70 federal.
7. Cash App Taxes mentioned
   Cash App Taxes - Free, including Schedule C.
8. Keeper mentioned
   - Keeper - Not a filer first;
9. QuickBooks Solopreneur mentioned
   - QuickBooks Solopreneur / Solo - If your bookkeeping is the bottleneck, this plus FreeTaxUSA at the end beats paying TurboTax to do both badly.
10. QuickBooks Solopreneur / Solo mentioned
    - QuickBooks Solopreneur / Solo - If your bookkeeping is the bottleneck, this plus FreeTaxUSA at the end beats paying TurboTax to do both badly.
11. Solopreneur mentioned
    - QuickBooks Solopreneur / Solo - If your bookkeeping is the bottleneck, this plus FreeTaxUSA at the end beats paying TurboTax to do both badly.
12. S-corp mentioned
    And once your net self-employment income clears roughly $75-100k, or you're considering an S-corp election, a real CPA (~$500-1,200) usually pays for itself in strategy that no software will surface.

Sources the engine cited

The answer, as recorded

## My actual recommendations, in order **1. FreeTaxUSA** - What I'd tell most freelancers to use. Schedule C, SE tax, home office, and 1099 income are all in the free federal tier; state is ~$15. There's no upsell wall the moment you type "self-employed," which is the single biggest annoyance with the big brands. Interface is plain but the math is the same math. ([freetaxusa.com](https://www.freetaxusa.com/), [comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)) **2. TurboTax Premium** - Worth the ~$130 federal + ~$65/state only if your situation is genuinely messy (multiple 1099s, vehicle and home office, crypto, K-1s, a spouse with equity comp) or if you dread the process enough that a good interview flow is worth paying for. It's the most polished walkthrough of Schedule C that exists. Otherwise you're paying a premium for UX. ([turbotax.intuit.com](https://turbotax.intuit.com/personal-taxes/self-employment-taxes/)) **3. H&R Block Self-Employed** - The middle option: roughly $85 federal + $37/state, most of TurboTax's hand-holding for meaningfully less, plus real human support and physical offices if you want to escalate. This is my pick if you want a brand-name product but not TurboTax's price. ([hrblock.com](https://www.hrblock.com/online-tax-filing/self-employed-online-tax-filing/)) **4. TaxSlayer Self-Employed** - Cheapest of the "guided" tier, usually under $70 federal. Good if you've filed a Schedule C before and just want a competent form-filler with quarterly estimate support. **5. Cash App Taxes** - Free, including Schedule C. Genuinely $0 federal *and* state. The catch: no multi-state filing, no part-year-resident returns in some cases, mobile-first, and no paid support. If you're a single-state freelancer with straightforward income, it's hard to beat free. ## Two things worth adding alongside - **Keeper** - Not a filer first; it's expense tracking that scans your bank/card feed for deductible business spending all year, then files. Good if your real problem is "I have no idea what I spent" rather than "filing is hard." - **QuickBooks Solopreneur / Solo** - If your bookkeeping is the bottleneck, this plus FreeTaxUSA at the end beats paying TurboTax to do both badly. ## The honest bottom line For freelancers, the software choice matters less than getting **quarterly estimated payments** right - that's where people actually get hurt, via underpayment penalties, not via picking the wrong app. And once your net self-employment income clears roughly $75-100k, or you're considering an S-corp election, a real CPA (~$500-1,200) usually pays for itself in strategy that no software will surface. One caveat on sources: a lot of what ranks for this query right now is AI-generated affiliate content with invented statistics. I've stuck to pricing that's verifiable on the vendors' own sites, but confirm current-season prices directly - they change every January and the "free" tiers narrow as filing deadline approaches. Sources: - [FreeTaxUSA](https://www.freetaxusa.com/) - [TurboTax Self-Employment](https://turbotax.intuit.com/personal-taxes/self-employment-taxes/) - [H&R Block Self-Employed](https://www.hrblock.com/online-tax-filing/self-employed-online-tax-filing/) - [PrimeWay FCU - tax software comparison](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes) - [NerdWallet - Best Tax Software](https://nerdwallet.com/taxes/learn/best-tax-software)

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