Square Payroll Review 2027: Pros, Cons and Verdict

Who Square Payroll suits

Square Payroll fits two kinds of business. The first already runs Square POS and wants timecards and tips to flow into payroll from Square POS and the Square Team App. The second pays only 1099 contractors and wants the cheapest way to do it.

For employees, there is one plan: $35/mo plus $6 per person paid, month to month. It files federal and state taxes in all 50 states and DC, and multi-state payroll is included. For contractors only, there is a plan at $6 per contractor paid with no base fee that files 1099-NECs.

This review is based on Square's payroll pricing page and its state tax help articles, checked November 12, 2026.

Who should skip it

Skip Square if you have employees in Ohio, Pennsylvania or New York localities it doesn't support, or if any employee works across several tax jurisdictions. Square says it can't pay one employee who works in multiple tax jurisdictions, run multiple EINs under one account, or handle courtesy withholding.

If you want to try before you pay, Square lists no free trial.

What it costs at 5, 20 and 50 employees

Regular published price, employees only. Extra states don't change it.

Employees	Monthly cost
5	$65
20	$155
50	$335

Square has the lowest base fee of any full-service plan we compared, which makes it the cheapest for a single employee: $41/mo. Once you pay three or more people, Patriot Full Service costs less in one state, but Square includes every state, where Patriot charges $12/mo for each extra one.

What it files and what it leaves to you

Full-service payroll files and pays federal and state taxes in all 50 states and DC. Local taxes are filed only in supported jurisdictions. Elsewhere, Square calculates the tax and you file and pay it.

Square's help pages name the gaps:

• Ohio: municipalities not run by RITA, CCA or the City of Columbus are calculated but not filed or paid. You remit them yourself.
• Pennsylvania: Square files for Philadelphia, Pittsburgh and supported EIT/LST collectors. Others are yours to file, and Square gives you a quarterly wage report.
• New York: NYC and Yonkers withholding are supported. The Employer Compensation Expense Program is not.
• Kentucky: Square files state withholding, UI and new-hire reports, but its help article doesn't say it files city or county occupational taxes.

W-2s and 1099-NECs are filed, with digital delivery included. The contractor-only plan files 1099-NECs and nothing else: no tax payments or filings, and no multi-state.

Fees and traps

• Mailed paper W-2 and 1099 copies cost $3 per form per year.
• Workers' comp, paid amendment services, health insurance and 401(k) are add-ons, and the pricing page shows no prices for them.
• We found no tax penalty guarantee on Square's payroll, pricing or features pages.
• Direct deposit is 4 business days standard, with 2-day payroll on full-service. To use the faster options you need to process payroll by 8 p.m. PT.

Phone support runs Monday to Friday, 6 a.m. to 6 p.m. PT, with live setup help. Square's Trustpilot score of 3.5/5 from 7,536 reviews covers all of Square US, not payroll alone, so we don't treat it as a payroll rating.

Verdict

Square Payroll ranks fourth with a score of 8.4. It is the cheapest full-service plan for one employee, and its contractor-only plan has no base fee. It sits below Patriot because of the local tax gaps in Ohio, Pennsylvania and New York, the lack of a stated tax penalty guarantee, and no free trial. If you run Square POS, or you pay only contractors, start here. If you have staff in an unsupported locality, pick a plan that files local taxes.