What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-10-25

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-25

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 mentioned
   (Gusto (https://gusto.com/resources/articles/payroll/owners-draw-overview), 1-800Accountant (https://1800accountant.com/blog/how-to-pay-yourself-sole-proprietor))
2. Patriot mentioned
   Patriot Payroll - the value pick.
3. Patriot Payroll mentioned
   Patriot Payroll - the value pick.
4. OnPay mentioned
   OnPay - $40/mo + $6/person, one plan, no feature gating.
5. SurePayroll compared
   SurePayroll - cheapest full-service option in most comparisons (~$36/mo).
6. Collective mentioned
   Collective - not software, a done-for-you service for solopreneur S-corps (payroll + bookkeeping + tax filing + the S-corp election).
7. Square mentioned
   Square Payroll - the clear winner here.
8. Square Payroll mentioned
   Square Payroll - the clear winner here.
9. Wave mentioned
   Wave Payroll - $20/mo + $6/active person, sitting on top of Wave's free invoicing and accounting.
10. Deel mentioned
    Deel or Wise - if your contractors are overseas.
11. Wise mentioned
    Deel or Wise - if your contractors are overseas.

Sources the engine cited

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The answer, as recorded

Quick framing first, because it changes the answer completely: **if you're a sole proprietor or single-member LLC, you can't put yourself on payroll at all.** You take owner's draws and pay quarterly estimated self-employment tax - payroll software would be wasted money. Payroll only becomes relevant if you've elected S-corp taxation (then the IRS requires a "reasonable" W-2 salary), or if you're paying *other* freelancers. ([Gusto](https://gusto.com/resources/articles/payroll/owners-draw-overview), [1-800Accountant](https://1800accountant.com/blog/how-to-pay-yourself-sole-proprietor)) ## If you're an S-corp owner paying yourself **Patriot Payroll** - the value pick. Full Service is about $37/mo + $5/worker, Basic (you file taxes yourself) $17/mo + $4. For one owner-employee running the same salary every month, you don't need more than this, and nothing else is cheaper for full tax filing. **Gusto** - what I'd pick if I wanted the S-corp hand-holding. It's the one built around owner-employees specifically: reasonable-salary calculator, Form 2553 S-corp election help, automatic W-2/1099 at year end. Starts around $49/mo + $6/person, so you're paying ~$15/mo extra over Patriot for the compliance guardrails. **OnPay** - $40/mo + $6/person, one plan, no feature gating. Best if you work in multiple states or want zero add-on surprises; multi-state and year-end filings are included rather than upsold. **SurePayroll** - cheapest full-service option in most comparisons (~$36/mo). Barebones interface, but it runs a one-person S-corp payroll fine. **Collective** - not software, a done-for-you service for solopreneur S-corps (payroll + bookkeeping + tax filing + the S-corp election). Several hundred a month, but it replaces your accountant too. Worth it only if the S-corp admin is genuinely eating your time. ## If you're a freelancer paying other freelancers **Square Payroll** - the clear winner here. Contractor-only is **$6 per contractor you actually pay that month, no base fee**. Pay nobody, pay nothing. Handles 1099-NECs automatically. **Gusto's contractor-only plan** - $35/mo + $6/contractor, billed only in months you run payments. Pricier than Square, but it's the right call if you expect to hire W-2 employees later, since you upgrade in place instead of migrating. **Wave Payroll** - $20/mo + $6/active person, sitting on top of Wave's free invoicing and accounting. Good if you want one free-ish tool doing invoices, books, and contractor payments together. **Deel or Wise** - if your contractors are overseas. Standard US payroll tools handle international payouts badly or not at all. **My actual recommendation:** sole prop → skip payroll entirely, use a bookkeeping tool and set aside estimated taxes. S-corp → Patriot if you're comfortable with payroll mechanics, Gusto if you want the compliance safety net. Paying contractors → Square Payroll. One caveat on the numbers: several of the comparison figures above come from Gusto-published pages, which naturally frame Gusto well. Verify current pricing on each vendor's own page before committing - payroll pricing changed a lot in 2025-26. Sources: - [Gusto - owner's draw overview](https://gusto.com/resources/articles/payroll/owners-draw-overview) - [1-800Accountant - how to pay yourself as a sole proprietor](https://1800accountant.com/blog/how-to-pay-yourself-sole-proprietor) - [Gusto - best contractor payroll software 2026](https://gusto.com/resources/best-contractor-payroll-software) - [Gusto - Square Payroll pricing 2026](https://gusto.com/resources/guides/switch-payroll-providers/square-pricing) - [Gusto - best payroll services for a single-employee business](https://gusto.com/resources/best-payroll-service-for-one-employee) - [Gusto - best cheap payroll services 2026](https://gusto.com/resources/best-cheap-payroll-services) - [Collective - payroll solutions for solopreneurs](https://www.collective.com/blog/money-management/payroll-solutions-for-solopreneurs-a-comparison-guide) - [Software Finder - best payroll for S-corp](https://softwarefinder.com/resources/best-payroll-for-s-corp) - [Self-Employed.com - affordable payroll software 2026](https://www.selfemployed.com/affordable-payroll-software-2026/)

Near this answer

The same question, recorded on other dates: 2026-10-23, 2026-10-21, 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.

payroll software, asked for other audiences: small businesses (asked 2026-10-25), nonprofits (asked 2026-10-25).

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

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