Contractor Payroll Report
Which Payroll Software Handles 1099 Contractors Well?
We priced every major contractor payroll platform for 2026, including the rules that changed this year. The cheapest option depends entirely on how many contractors you pay.
Published
July 2026
Coverage
6 platforms
Research Base
Live 2026 vendor pricing
Read Time
11 min
The Rule That Just Changed
The 1099 reporting threshold moved. For tax years beginning after 2025, IRS guidance raises the 1099-NEC and 1099-MISC threshold from $600 to $2,000. A lot of vendor marketing still quotes $600. Rely on current IRS guidance, not the pricing page. Separately, any business filing 10 or more information returns must file electronically, so paper filing is no longer an option for most.
$2,000
the new 1099-NEC threshold for tax years after 2025, up from $600
$25/mo
QuickBooks Contractor Payments, covering 20 contractors, the volume winner
$0 base
Square Payroll's contractor plan, pay only per contractor
120+
countries Gusto pays contractors in, the international pick
Monthly Cost for 10 Contractors (2026, USD)
Base fee plus per-contractor charges, at standard rates rather than introductory offers.
Sources: Gusto pricing page (2026), QuickBooks Contractor Payments pricing, Fit Small Business payroll review (2026), Wingspan contractor services guide (2026). Pricing is subject to change, confirm with the vendor before buying.
Platform Comparison
| Platform | Contractor Pricing | Files 1099s | International |
|---|---|---|---|
| QuickBooks Contractor Payments | $25/mo, 20 contractors included, $2 each extra | ✓ | ✗ |
| Gusto Contractor Only | $35/mo + $6 per contractor | ✓ | ✓ 120+ countries |
| Square Payroll | $0 base, per-contractor fee only | ✓ | ✗ |
| Rippling | $35 base + $8 per person | ✓ | ✓ 160+ countries |
| Wave Payroll | Low-cost, pairs with free Wave accounting | ✓ | ✗ |
| OnPay | Flat pricing, employees and contractors | ✓ | ✗ |
What Trips People Up
- Assuming the $600 threshold still applies. It is $2,000 for tax years after 2025.
- Paying contractors by card or PayPal, which excludes them from your 1099 totals entirely
- Comparing base fees while ignoring per-contractor charges that compound
- Not collecting a W-9 before the first payment goes out
What Good Contractor Payroll Does
- Collects W-9s and validates TINs at onboarding, not in January
- Generates and e-files 1099-NEC forms with the IRS automatically
- Sends contractor copies without you printing anything
- Syncs the payments straight into your accounting ledger
Three Rules for Choosing
Match the pricing model to your headcount. QuickBooks bundles 20 contractors into a flat $25, which is unbeatable at volume. Per-contractor pricing like Gusto's $6 each is cheaper only when you pay a handful of people.
Let your accounting platform decide it. If your books are in QuickBooks, Contractor Payments syncs natively and your 1099 mapping stays clean. Fighting an integration to save a few dollars a month is a false economy.
Pay for compliance, not features. Worker classification rules are in flux, with the DOL reworking its independent-contractor framework in 2026. Automatic TIN validation and e-filing are worth more than an HR dashboard you will never open.
Match Your Profile to a Platform
1 to 5 Contractors
Occasional freelancers, no employees
Year-1 cost: $0 to $360
10 to 20 Contractors
Regular contractor roster, books in QuickBooks
Year-1 cost: ~$300
Global or Mixed Team
Employees plus contractors, some overseas
Year-1 cost: $1,100 to $1,600+
Software Alone Will Not Save You
Even the best platform files whatever you feed it. If your expense accounts are mapped to the wrong 1099 box, contractors vanish from the form. Get the setup right first: see our guides on mapping 1099 accounts and processing and filing 1099s.
Free Contractor Payroll Assessment
Not Sure Which Platform Fits Your Contractor Roster?
We map your contractor count, payment methods, and accounting stack to the lowest-cost compliant setup, then configure the 1099 mapping so year-end runs clean.
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