What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-10-21

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-21

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

The question asked, verbatim: best payroll software for freelancers

Brands named, in the order the engine gave

1. Gusto recommended
   Gusto - my default recommendation.
2. OnPay mentioned
   OnPay - best value if you want one flat price with nothing feature-gated.
3. Patriot mentioned
   Patriot Payroll - the budget pick at $17/mo basic, $37/mo with tax filing.
4. Patriot Payroll mentioned
   Patriot Payroll - the budget pick at $17/mo basic, $37/mo with tax filing.
5. QuickBooks mentioned
   QuickBooks Payroll - only if you already live in QuickBooks for bookkeeping.
6. Square mentioned
   Square Payroll - cheapest contractor-only option, and the obvious choice if you already take payments through Square.
7. Square Payroll mentioned
   Square Payroll - cheapest contractor-only option, and the obvious choice if you already take payments through Square.
8. Deel mentioned
   Deel - the one to use for international contractors.
9. Wise mentioned
   - Best Payroll Software for 1099 Contractors (Wise) (https://wise.com/us/blog/batchtransfer-payroll-software-1099-contractors)

Sources the engine cited

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The answer, as recorded

Quick framing first, because it changes the answer: if you're a sole proprietor or single-member LLC, **you don't need payroll at all** - you pay yourself with owner's draws and handle quarterly estimated taxes. Payroll software only becomes relevant if you've elected S-corp status (so you must pay yourself a W-2 salary), or if you're paying other freelancers/subcontractors. Here's who I'd use in each case. ## If you're an S-corp paying yourself a salary 1. **Gusto** - my default recommendation. Clean interface, files your 941/940/W-2 automatically, handles the owner-salary case well, and it's the one most accountants and bookkeepers already know how to work with. ~$49/mo + $6/person. 2. **OnPay** - best value if you want one flat price with nothing feature-gated. $40/mo + $6/person, all tax filings included, no upsell tiers. Slightly plainer than Gusto but genuinely full-service. 3. **Patriot Payroll** - the budget pick at $17/mo basic, $37/mo with tax filing. Unlimited pay runs. Less polished, but for a single-employee S-corp running the same salary every month, polish barely matters. 4. **QuickBooks Payroll** - only if you already live in QuickBooks for bookkeeping. The integration is the entire argument; standalone, the others are better. ## If you're paying freelancers/contractors 1. **Gusto's contractor-only plan** - $35/mo + $6 per contractor, and it only bills in months you actually pay someone. Automatic 1099-NEC filing and contractors onboard themselves. 2. **Square Payroll** - cheapest contractor-only option, and the obvious choice if you already take payments through Square. 3. **Deel** - the one to use for international contractors. 150+ countries, multi-currency, handles the compliance paperwork; US contractors from ~$15/mo. 4. **Wave Payroll** - worth a look if you want free invoicing and accounting as the base layer and payroll bolted on top. One 2026 detail worth knowing: the 1099-NEC filing threshold rises from $600 to $2,000 for payments made in 2026, so if you pay occasional small-dollar freelancers, you may have fewer forms to file than you expect. My honest take: **Gusto** if you want it to just work and play nicely with your accountant, **OnPay** if you'd rather not think about pricing tiers, **Patriot** if you're optimizing on cost - and nothing at all if you're a plain sole proprietor, where a good invoicing/bookkeeping tool plus quarterly estimates is the real answer. Sources: - [Affordable Payroll Software for Self-Employed Business Owners in 2026](https://www.selfemployed.com/affordable-payroll-software-2026/) - [10 Best Payroll Apps for Freelancers in 2026](https://work-club.com/best-payroll-apps-freelancers-2026/) - [8 Best Contractor Payroll Software for 2026 (Gusto)](https://gusto.com/resources/best-contractor-payroll-software) - [Best Payroll Software for 1099 Contractors (Wise)](https://wise.com/us/blog/batchtransfer-payroll-software-1099-contractors) - [Best 1099 software for small businesses (Relay)](https://relayfi.com/blog/best-1099-software-small-businesses-guide)

Near this answer

The same question, recorded on other dates: 2026-10-18, 2026-10-15, 2026-10-13, 2026-10-10, 2026-10-08, 2026-10-06, 2026-10-05, 2026-10-03, 2026-10-01, 2026-09-26, 2026-09-24.

payroll software, asked for other audiences: small businesses (asked 2026-10-21), nonprofits (asked 2026-10-21).

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

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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.