Navigating the New 1099 Filing Rules Under the OBBBA
Stay ahead of evolving Form 1099 regulations by learning the latest compliance requirements, IRS enforcement updates, and proven reporting best practices.
Overview
What you'll learn
Course Overview
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 BBB.
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.
Key Areas: expand_more
By the end of this session, participants will be able to:
- 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.
Why You Should Attend: expand_more
The attendees will understand
- 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
The Big Beautiful Bill is coming—and with it, a major shift: the long-standing $600 threshold for Form 1099 reporting is on the chopping block. Are you ready for what’s next?
Who should attend? expand_more
- Accountants
- Bookkeepers
- Office Managers
- Human Resources Professionals
- Compliance Professionals
Instructor
Jason Dinesen
EA, LPA
Jason Dinesen (EA, LPA) is a tax nerd, entrepreneur, tax expert and a well known presenter of continuing education courses. He has an impeccable acumen for tax subjects, by virtue of which, he is known to create very well researched course materials helping in...
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