Will You Be Getting a 1099 or a W-2?

Tax season can be daunting for trucking owner-operators and company drivers alike. Knowing whether you’ll receive a 1099 or a W-2 is essential for understanding your tax obligations and ensuring compliance. Here's a guide to help you navigate these tax forms, who gets what, and how to prepare.

What’s the Difference Between a 1099 and a W-2?

Form 1099

This is issued to independent contractors, including owner-operators contracted by motor carriers or brokers. It reports the total amount paid to the contractor over the year. More specifically, it can be called a 1099-NEC (formerly 1099-MISC). 

Independent contractors are responsible for self-employment taxes (Social Security and Medicare) and quarterly estimated taxes, so some annual wages should be set aside for these obligations. 

Form W-2

This is for company employees, such as company drivers. It shows total wages earned and taxes withheld (federal income tax, Social Security, Medicare, and potentially state and local taxes).

W-2 employees have taxes deducted automatically, reducing their administrative burden.

Who Gets a 1099 vs. a W-2 in Trucking?

Contracted Carriers/Owner-Operators: If they’re hired as independent contractors by a motor carrier, they typically receive a 1099. They are responsible for managing their taxes, fuel expenses, insurance, and maintenance costs.

Company Drivers: Receive a W-2 reflecting their employee status. Taxes are automatically deducted, and the company may provide benefits like health insurance or retirement plans.

When a 1099 Isn’t Issued

Brokers often don’t issue 1099s to independent carriers structured as corporations. 

Payments made via third-party services like PayPal or credit cards may also not require a 1099 if the payment processor reports the transactions to the IRS on a 1099-K. In 2024, the IRS is updating the threshold for 1099-K’s to $5,000. 

Timelines for 1099s and W-2s

1099 Forms

Must be issued by January 31st to independent contractors and filed with the IRS by the same date (or February 28th if filing by mail). Contractors need to ensure their total revenue is reported accurately for tax filing.

W-2 Forms

It must also be issued to employees by January 31st and includes detailed reporting of wages, tax deductions, and benefits.

How to Prepare for Tax Season

  1. Stay Organized Throughout the Year:some text
    • Ensure all W-9 forms (used to collect contractor details by companies) are on file and updated annually.
    • Use a robust TMS (Transportation Management System) or ERP (Enterprise Resource Planning) software to track logistics, payments and documentation.
  2. Use 1099 Preparation Software:some text
    • Tools like Track1099, Tax1099, or accounting software like QuickBooks can simplify 1099 issuance for motor carriers hiring contractors.
    • Automate form generation and e-filing to reduce errors and save time.
  3. Set Up a Tax Checklist:some text
    • Confirm that all payments to independent contractors exceeding $600 in the calendar year are appropriately documented.
    • Verify business details, including EINs and names, to avoid discrepancies.
  4. Consult a Tax Professional:some text
    • Whether you're a contracted carrier or a motor carrier issuing 1099s, professional advice can ensure compliance and help minimize tax liabilities.

Key Takeaways for Trucking Professionals

  • Owner-operators should expect a 1099 and plan to manage their own tax filings.
  • Company drivers can rely on their W-2 for pre-deducted tax contributions.
  • Motor carriers hiring independent contractors must issue 1099s unless exemptions apply (e.g., paying businesses with EINs or using third-party processors).
  • Use software and systems to streamline the tax process and avoid errors.

Understanding the distinctions between 1099s and W-2s and implementing proper record-keeping allows trucking professionals to stay prepared and minimize stress during tax season.