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.

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

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?

• 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.

For Recorded and E-transcript Participants: If you have signed up for the “Recorded” class or for the “E-transcript”, you will get access to the “Recording link” or the “PDF” within 24-48 hours of the live class.

SPEAKER

Jason Dinesen, LPA, EA

Jason Dinesen is the President of Dinesen Tax & Accounting, P.C., a public accounting firm in Indianola, Iowa. His practice focuses on accounting and bookkeeping services, tax preparation and business advising to individuals with a business focus ranging from home-based businesses to multistate corporations and not-for-profits. Dinesen has extensive experience working with a third-party administrator of retirement plans and is a prior presenter of multiple 1099 seminars. Dinesen majored in corporate communications with a minor in management from Simpson College.

Why You Should Subscribe to Our Unlimited Webinar?

Unlimited Live and On-Demand Courses

Watch all live or recorded webinars (up to 120 minutes long). Get instant access to a library of more than 500 high quality courses presented by best-in-class presenters.

CEUs: APA, CPE, SHRM and HRCI Credits

Fulfil your recertification requirements by earning CEUs from APA, CPE, SHRM and HRCI.

Free Access to Course Materials

Each program comes with Additional Course Materials, which you can download and read anytime.

Additional Discounts

Get flat 20% discount on Premium Product Category like, Long Hour Webinars.

SUBSCRIBE NOW