What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-09-22

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-22

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. S-corp mentioned
   You only need it once you've elected S-corp status and have to pay yourself a W-2 salary.
2. Patriot Payroll mentioned
   Patriot Payroll - cheapest full-service option at roughly $17/mo + $4/employee, so ~$42/mo for a one-person S-corp.
3. Gusto mentioned
   Gusto - the one I'd pick if you want hand-holding rather than the lowest price.
4. OnPay mentioned
   OnPay - flat $40 + $6/person, no tiered upsells, and it's well regarded for handling unusual situations.
5. QuickBooks mentioned
   QuickBooks Payroll - only if you already live in QuickBooks.
6. Square recommended
   Square Payroll - the value pick, and my default recommendation here.
7. Deel mentioned
   Deel - the answer if any of your contractors are outside the US.
8. Wave mentioned
   Wave Payroll - cheap and fine if you're already on Wave's free accounting, but self-service tax filing in most states means more manual work.
9. Skip Rippling mentioned
   Skip Rippling.
10. Rippling mentioned
    Skip Rippling.

Sources the engine cited

The answer, as recorded

Quick framing, because "payroll for freelancers" means two different things and the answer differs: ## If you're a freelancer paying *yourself* **First: check whether you need payroll at all.** If you're a sole proprietor or single-member LLC (default tax treatment), you don't run payroll - you take owner's draws and pay quarterly estimated taxes. Payroll software is wasted money. You only need it once you've elected S-corp status and have to pay yourself a W-2 salary. Assuming you're S-corp: 1. **Patriot Payroll** - cheapest full-service option at roughly $17/mo + $4/employee, so ~$42/mo for a one-person S-corp. It files federal and state taxes in all 50 states. For a single-employee payroll that never changes month to month, the extra features you'd pay for elsewhere don't earn their keep. ([Patriot](https://www.patriotsoftware.com/payroll/best-payroll-software-for-small-businesses/), [comparison](https://trustedproductscout.com/best-payroll-software-for-single-employee-s-corps-2026-guide/)) 2. **Gusto** - the one I'd pick if you want hand-holding rather than the lowest price. It has S-corp-specific features like reasonable-compensation tracking, clean onboarding, and it doubles as your contractor-payment tool if you also hire out work. Roughly $50-60/mo all-in for one person. ([Gusto](https://gusto.com/resources/guides/best-payroll-service-for-one-employee)) 3. **OnPay** - flat $40 + $6/person, no tiered upsells, and it's well regarded for handling unusual situations. Good middle option. ([OnPay](https://onpay.com/insights/best-small-business-payroll-software-picks/)) 4. **QuickBooks Payroll** - only if you already live in QuickBooks. Otherwise it's the priciest of the four (~$678/yr for one employee) for no real gain. ## If you're a freelancer/small business *paying other* freelancers 1. **Square Payroll** - the value pick, and my default recommendation here. Contractor-only accounts have **no monthly base fee**, just $6 per contractor you actually pay that month. Includes 1099-NEC e-filing. If you pay two people some months and zero in others, you pay almost nothing. ([Square pricing](https://gusto.com/resources/guides/switch-payroll-providers/square-pricing)) 2. **Gusto** - also offers contractor-only pricing, collects W-9s at onboarding, and auto-files 1099-NECs for anyone over $600. Worth the premium over Square if you expect to add W-2 employees later, since you won't have to migrate. 3. **Deel** - the answer if any of your contractors are **outside the US**. It localizes contracts and collects the right tax forms across 150+ countries, which is the part that genuinely bites you if you get it wrong. Around $49/contractor/mo, so overkill for domestic-only work. ([comparison](https://www.launchadvisor.co/guides/gusto-vs-rippling-vs-deel-vs-remote-freelancer-independent-creator)) 4. **Wave Payroll** - cheap and fine if you're already on Wave's free accounting, but self-service tax filing in most states means more manual work. **Skip Rippling.** It's a full workforce/IT platform and is badly oversized for anyone who'd describe themselves as a freelancer. It makes sense once you're an agency with real headcount. One caveat on the numbers: published pricing varied between the sources I checked (Gusto's base plan was quoted as both $40+$6 and $50+$12 depending on the page), so treat these as ballpark and confirm on the vendor's own pricing page before committing. Sources: - [Patriot Software - best payroll software for small businesses](https://www.patriotsoftware.com/payroll/best-payroll-software-for-small-businesses/) - [Gusto - best payroll service for one employee](https://gusto.com/resources/guides/best-payroll-service-for-one-employee) - [Gusto - Square Payroll pricing 2026](https://gusto.com/resources/guides/switch-payroll-providers/square-pricing) - [OnPay - best small business payroll software picks](https://onpay.com/insights/best-small-business-payroll-software-picks/) - [Best payroll software for single-employee S corps 2026](https://trustedproductscout.com/best-payroll-software-for-single-employee-s-corps-2026-guide/) - [Launch Advisor - Gusto vs Rippling vs Deel vs Remote for freelancers](https://www.launchadvisor.co/guides/gusto-vs-rippling-vs-deel-vs-remote-freelancer-independent-creator) - [People Managing People - best payroll software for contractors](https://peoplemanagingpeople.com/tools/best-payroll-software-for-contractors/)

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