2026 Form 1099 Reporting: New Rules, Thresholds & Key Updates
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Webinar Overview
About this Webinar:
In this timely, relevant, and actionable session, Jason Dinesen known nationwide as “The 1099 Guy” guides attendees through the practical realities of Form 1099 compliance. This session goes beyond the basics and dives deep into due diligence, backup withholding, and how to handle missing SSNs, all while preparing for increased IRS scrutiny and a dramatically changing landscape under the OBBB.
Whether you’re an AP professional, accountant, or small business owner, you’ll leave this course with clear guidance on how to protect your organization from penalties, defend against IRS pushback, and build bulletproof compliance procedures no jargon, no fluff, just real-world insight you can apply immediately.
This webinar will cover Form 1099-NEC for independent contractors, and Form 1099-MISC for reporting payments such as rent. We will also cover Form 1099-K and how to deal with payments made via apps such as PayPal and Venmo. IRS penalties for failure to file correct 1099s continue to rise, and the IRS is cracking down on 1099-related compliance such as backup withholding.
Session Highlights:
Evaluate when a payment is reportable on Form 1099 and who is responsible for issuing the form.
Apply the correct due diligence procedures for soliciting and maintaining Form W-9s, including best practices even when reporting isn’t initially required.
Determine when backup withholding is mandatory under IRC § 3406 and how to calculate, deposit, and report the withheld amounts.
Implement step-by-step procedures for handling CP-2100 letters and B Notices, including differentiating between first and second notices.
Avoid common compliance pitfalls such as missing TINs, late filings, and improper e-filing—and understand how to make a successful reasonable cause defense if penalties are assessed.
Prepare for future compliance under the Big Beautiful Bill, including the anticipated end of the $600 reporting threshold and updates to electronic filing systems like IRIS and FIRE.
When to file: the $600 threshold
When to file: corporations
When to file: credit card and payment apps such as Venmo
Filing matters including the e-file mandate and how to file
Form W-9
Backup withholding
Why You Should Attend:
The Big Beautiful Bill is bringing significant changes to Form 1099 reporting, potentially reshaping the long-standing $600 reporting threshold and creating new considerations for businesses, freelancers, and tax professionals. Join us to understand what these changes could mean for you, stay ahead of evolving tax requirements, and prepare for the road ahead with greater clarity and confidence.
Who Should Attend:
Accountants
Bookkeepers
Office Managers
Human Resources Professionals
Compliance Professionals
Business Owners
During the Q&A session following the live event, ask a question and get a direct response from our expert speaker.
Important Notice for Our “Live” Attendees: If you have enrolled in the “Live Webinar,” you will get your instruction kit before 24 hours of the live class.
Enrolled attendees earn CE credit for this course
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SHRM - 1.5 Credit
This program is recognized by SHRM to offer Professional Development Credits (PDCs) for SHRM-CP® and SHRM-SCP® credential holders. This program is valid for 1.5 PDCs toward SHRM recertification requirements.
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HRCI - 1.5 Credit
This program has been approved for 1.5 HR (General) recertification credit hours toward aPHR™, aPHRi™, PHR®, PHRca®, SPHR®, GPHR®, PHRi™, and SPHRi™ recertification through the HR Certification Institute® (HRCI®).
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Content Quality and Compliance
“The courses, webinars, articles, and learning materials available on this educational platform are developed in accordance with the standards and guidelines of recognized professional credit and continuing education (CEU) providers. All content is thoroughly researched, reviewed, and verified prior to publication.”
Meet Your Instructor
Jason Dinesen, EA
Tax Professional
Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason founded a tax-preparation firm in 2009, and ran it through June of 2025. He now focuses on teaching and other work at Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals, to podcast production to radio and journalism content.
Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics. Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe’s in West Des Moines, Iowa. He still teaches on 1099s and around 30 other tax topics.
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