What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-27
Claude (Anthropic) with web search claude-opus-5 asked 2026-09-27
On 2026-09-27, Claude (Anthropic) with web search was asked "best tax preparation software for freelancers". It named 12 brands; the first six, in order, were FreeTaxUSA, TurboTax, TurboTax Premium, QuickBooks, QuickBooks Self-Employed and H&R Block.
| Question | best tax preparation software for freelancers |
|---|---|
| Asked on | 2026-09-27 |
| Engine | Claude (Anthropic) with web search |
| Model | claude-opus-5 |
| Brands named | 12 |
| Sources cited | 5 |
| Audience | freelancers |
| Coverage | Coverage: Claude (Anthropic) with web search. Other engines not included. |
| Last verified |
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
- FreeTaxUSA recommended
FreeTaxUSA - my default pick for most freelancers.
- TurboTax recommended
TurboTax Premium (formerly Self-Employed) - if you want the hand-holding.
- TurboTax Premium recommended
TurboTax Premium (formerly Self-Employed) - if you want the hand-holding.
- QuickBooks recommended
It also imports from QuickBooks Self-Employed cleanly.
- QuickBooks Self-Employed recommended
It also imports from QuickBooks Self-Employed cleanly.
- H&R Block recommended
H&R Block Self-Employed - the middle ground.
- H&R Block Self-Employed recommended
H&R Block Self-Employed - the middle ground.
- TaxSlayer Self-Employed recommended
TaxSlayer Self-Employed - cheapest paid tier with support.
- Cash App Taxes recommended
Cash App Taxes - free federal and free state.
- QuickBooks Solopreneur mentioned
Same for QuickBooks Solopreneur if you want bookkeeping + tax in one.
- Solopreneur mentioned
Same for QuickBooks Solopreneur if you want bookkeeping + tax in one.
- S-corp mentioned
- If you have an S-corp election, multi-state income, foreign clients, or over ~$150k net SE income, skip all of these and hire a CPA.
What Claude (Anthropic) with web search answered about tax preparation software for freelancers on 2026-09-27: 12 brands named, 5 sources cited. This question is asked again on the nightly schedule and each new answer gets its own dated page.
Free brand monitors are closed for now. This record stays free to read and share at its permanent address.
Answer Watch Pro: daily change alerts for up to 5 brands in what one AI answer engine says, history, CSV export. Coverage: Claude (Anthropic) with web search. Other engines not included, for 79 USD a month. Get the membership. The checkout is titled Bikoosh Watch: one membership shared across Bikoosh products. After paying, come back to https://bikoosh.com/answers/activate and enter the email you paid with.
Sources the engine cited
| Source | Type |
|---|---|
| walletgrower.com | other |
| primewayfcu.com | other |
| turbotax.intuit.com | other |
| hrblock.com | other |
| ifeeltech.com | other |
The answer, as recorded
For a freelancer with a Schedule C, here's what I'd actually recommend, in order: **1. FreeTaxUSA - my default pick for most freelancers.** Schedule C, SE tax, home office, and 1099 income are all in the free federal tier; you only pay for state (~$15-16). It's an IRS-authorized e-file provider that's been around since 2001. The interface is plain and form-like rather than hand-holding, but the math is the same and you keep ~$100+. If your situation is one or two 1099s, some expenses, and a home office, there's no good reason to pay more. **2. TurboTax Premium (formerly Self-Employed) - if you want the hand-holding.** Around $129 federal plus state. The Schedule C interview is genuinely the best in the category: it asks questions in plain English and walks through vehicle, home office, health insurance, and retirement contributions in order. Worth it if your return is messy, it's your first year self-employed, or your time is worth more than the price difference. It also imports from QuickBooks Self-Employed cleanly. **3. H&R Block Self-Employed - the middle ground.** Roughly $85 federal + ~$37/state. Does nearly everything TurboTax does for less, and it's the only one of these with real in-person offices if you get stuck or get an IRS letter. **4. TaxSlayer Self-Employed - cheapest paid tier with support.** Noticeably less than TurboTax/H&R Block, handles Schedule C and quarterly estimated tax planning fine. The UI is dated; pick it if you want a price break but still want phone/email support included. **5. Cash App Taxes - free federal *and* free state.** Supports Schedule C. The catch: one state only, no multi-state, no foreign income, and support is thin. Fine for a simple solo freelance return if you want to pay literally nothing. **Worth pairing with any of these: Keeper** (~$20/mo or so) if your problem is tracking deductions during the year rather than filing in April. It scans linked accounts for write-offs and can file too. Same for QuickBooks Solopreneur if you want bookkeeping + tax in one. Two caveats worth your attention: - **Prices shift every filing season and jump as April approaches** - treat the numbers above as approximate for the 2026 season and check the site before you commit. Several of the "2026 review" pages I found are affiliate content with inconsistent figures, so I'd verify pricing directly on the vendor's page. - **If you have an S-corp election, multi-state income, foreign clients, or over ~$150k net SE income, skip all of these and hire a CPA.** The retirement-plan and entity decisions at that level save more than any software's deduction finder. Sources: - [FreeTaxUSA / TurboTax / H&R Block comparison - WalletGrower](https://walletgrower.com/compare/turbotax-vs-hr-block-vs-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) - [TurboTax Self-Employment Tax Hub](https://turbotax.intuit.com/personal-taxes/self-employment-taxes/) - [H&R Block Self-Employed Online](https://www.hrblock.com/online-tax-filing/self-employed-online-tax-filing/) - [Tax Software for Small Business comparison - iFeeltech](https://ifeeltech.com/blog/tax-software-small-business-turbotax-hrblock-freetaxusa)
Near this answer
The same question, recorded on other dates: 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 2026-09-27), nonprofits (asked 2026-09-27).
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.