Form 1099 Mistakes To Avoid In 2025: New OBBB Updates And IRS Rules

Event Overview

Live Webinar - December 11, 2025 | Speaker: Jason Dinesen | 90 Minutes | HRCI, SHRM & NASBA-Approved Class

Form 1099 Reporting is changing fast, and the pressure on organizations to stay compliant has never been higher. In this power-packed session, Jason Dinesen, nationally recognized as “The 1099 Guy”, breaks down everything you need to know about Form 1099 rules, IRS expectations, and the major compliance shifts coming under the Big Beautiful Bill (OBBB).

In just 90 minutes, you’ll learn exactly how to navigate Form 1099 requirements, strengthen your due diligence process, reduce penalty exposure, and confidently handle backup withholding, B Notices, W-9s, and payments made through modern platforms like PayPal and Venmo. No jargon. No theory. Just real-world Form 1099 strategies you can apply immediately.

Whether you’re in accounting, HR, payroll, or small business operations, this webinar gives you the clarity and tools you need to build a reliable, audit-ready Form 1099 procedure that protects your organization year-round.

Why This Webinar Matters

Form 1099 Reporting is one of the most common, confusing, and costly compliance areas for businesses. With IRS scrutiny rising and the traditional $600 threshold likely to change under OBBB, even small mistakes can lead to steep penalties, backup withholding obligations, and time-consuming IRS correspondence.

This session helps you close the knowledge gaps that cause most Form 1099 issues. You’ll learn how to correctly identify reportable payments, manage vendor documentation, handle app-based transactions, and stay ahead of upcoming IRS filing changes through IRIS and FIRE.

If you want to avoid compliance traps and ensure your Form 1099 process is airtight for 2025 and beyond, this training is essential.

Why You Should Attend

You will gain practical, actionable insights, including how to:

• Build an audit-proof Form 1099 Reporting process from start to finish
• Apply due diligence steps for W-9s, TIN validation, and documentation
• Handle backup withholding correctly when vendors don’t provide valid SSNs/EINs
• Manage CP-2100 letters and B Notices with confidence
• Stay compliant as OBBB reshapes the future of Form 1099 thresholds and e-filing rules

Who Should Attend

This webinar is ideal for:

• Accountants & Bookkeepers
• AP & Payroll Professionals
• HR & Compliance Leaders
• Office Managers
• Controllers & CFOs
• Small Business Owners

Anyone responsible for Form 1099 Reporting or vendor compliance

Session Format

Live Webinar: Attend in real time and get your questions answered during the Q&A.

Recording & E-Transcript: Can’t join live? Receive the full session recording and e-transcript within 24–48 hours.

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