Form 1099 and Worker Classification Issues

With constant revisions to the law and the related rule changes, it is crucial to remain up-to-date with the current information reporting laws to avoid those dreaded penalties and interest, not to mention the time consumed to make corrections. Whether you are new or seeking an update, this course will provide CPA’s, Accounts Payable, Payroll, and Tax with plain English guidance to help minimize 1099 mistakes while breaking down the toughest 1099 payee and payment reporting situations.

In this course, industry expert and corporate tax attorney Steven D. Mercatante Esq. takes a look at some of the more common problems experienced by CPA’s, accounts payable, and tax departments related to documenting, validating, and reporting payee information on IRS Forms 1099. He identifies key issues and best-practices for addressing them.

• Determine which 1099 to use and watch out for key trouble spots on the most commonly filed Forms 1099
• Why worker classification issues are impacting your 1099 vendor payments in 2025
• Tricky 1099 situations: rent, leases, prizes and awards, recognize which boxes to report attorney and settlement payments, decode what "damages" payments mean for AP purposes, identify the difference between box 6 and 1099-NEC box one medical service provider payments, discover when the reporting does not always follow the payment, determine which boxes to report non-qualified deferred compensation
• W-9 document validation best practices with a focus on situations when multiple names are provided, handling undocumented payees, exempt organization payees, and IRS TIN Match Program best practices
• The reportable payee when you pay sole proprietors, LLCs, payee's merged or bought by another, S-Corps, agents, or middlemen
• Valuable tips for E-Filing and for using the Combined Federal/State Filing Program
• Backup withholding guidance designed to make your job easier, including a detailed discussion of the Form 1099-MISC and Form 1099-NEC's Box 4 versus usage of Form 945

• Recognize how to determine which 1099 to use and watch out for key trouble spots on the most commonly filed Forms 1099
• Describe why worker classification issues are impacting your 1099 vendor payments in 2025
• Discover key Department of Labor and State Level documentation requirements, while learning how they interrelate with Treasury Department mandates
• Identify tricky 1099 situations
• Identify W-9 document validation best practices with a focus on situations when multiple names are provided, handling undocumented payees, exempt organization payees, and IRS TIN Match Program best practices
• Recognize how to identify the reportable payee when you pay sole proprietors, LLCs, payee's merged or bought by another, S-Corps, agents, or middlemen
• Identify how to use valuable tips for E-Filing and for using the Combined Federal/State Filing Program
• Recognize how to receive backup withholding guidance designed to make your job easier, including a detailed discussion of the Form 1099-MISC and Form 1099-NEC's Box 4 versus usage of Form 945

Who Will Benefit From This Webinar:
If you report payments on Forms 1099, supervise 1099 compliance and want to stay on top of changes in the law, or are a CPA and would benefit from assistance validating Forms 1099 this course is a must.

Why Attend This Webinar:
By attending, you’ll gain the clarity and practical knowledge needed to reduce compliance risk and ensure accurate, timely 1099 reporting—saving time, avoiding penalties, and enhancing your organization’s compliance performance.