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:

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.

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

Why You Should Attend:

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?

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 individuals and businesses with accounting, bookkeeping, tax preparation, and business advisory in various industries. Known for his sharp tax interpretations, he is one of the quickest to bring the analysis of the latest tax updates and IRS guidance to the professional community. Jason has coached over 200,000 accounting, tax, and HR professionals on various topics of accounting, individual taxation, corporate taxation, professional ethics and much more. He has presented over dozens of webinars on Form 1099 (MISC & R); marriage in the tax code; tax updates; the new Form W-4, payroll updates, filing status, tax credit and other issues relating to the modern-day household setting. Moreover, Jason is known to be producing every other webinar/course a little different and updated from the previous one. No wonder, he is a top ranked presenter whose webinars and self-study course materials are very well received by the audience. He also teaches 2 classes at Simpson College, Individual Income Tax and Business Analytics.

Credits

Frequently Asked Questions

Live training course/ webinar is an Online training seminar which you can access through your computer and laptop or phone and directly interact with our expert speaker and allow to ask questions during the Live webinar. Conference material used by our speaker to the Live webinar will be provide with your Instruction kit before the Training.

Recorded webinars or On-Demand are self-paced audio-visual training program that you can watch at your own pace to earn Continuing Education Units (if applicable). Online, recorded training courses are accessible whenever you choose, for an unlimited number of times. Additionally, you have three months from the purchase date to watch as many times as you like. After a live training or webinar has started, you will receive the instructions and link to access the recorded training course. If it has already been recorded, you can access it right away.

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2026 Form 1099 Compliance : New IRS Rules & OBBBA Updates

Course Type	HR & Payroll
Date & Time	Feb 4th 2026 01:00 PM ET
Duration	90 Minutes
Instructior	Jason Dinesen

Purchase Options

Live
Live session is a live webinar which you access through your computer and headphones and you can ask your questions directly to our speaker.

$ 155
Recorded
Recorded session is a recorded format of live webinar which you can access anytime at your convenience without any time limit.

$ 165
E-transcript
E-transcripts is a text version of a live webinar which you will get in pdf format.

$ 165
Live + Recorded
In live and recorded session you can access your live webinar and also access your recorded part of the webinar for your reference.

$ 175
Live + Recorded
+ E-transcript
Live session is a live webinar which you access through your computer and headphones and you can ask your questions directly to our speaker. Recorded session is a recorded format of live webinar which you can access anytime at per your convenience without any time limit. E-transcripts is a text version of a live webinar which you will get in pdf format.

$ 185
Recorded + E-transcript
Recorded session is a recorded format of live webinar which you can access anytime at your convenience without any time limit. E-transcripts is a text version of a live webinar which you will get in pdf format.

$ 175
Live + E-transcript
Live session is a live webinar which you access through your computer and headphones and you can ask your questions directly to our speaker.

$ 175
Recorded with Copyright
E-transcripts is a text version of a live webinar which you will get in pdf format. Copyright is a recorded session which you can share with your colleagues.

$ 195