Course Compliance

Mastering Form 1099 Due Diligence: Avoiding Pitfalls, Penalties & IRS Pushback

Mastering Form 1099 Due Diligence_jason dinesen_course compliance

Date: August 5, 2025 | Time: 10 AM {PST} | 01 PM {EST}
Duration: 90 Minutes | Speaker: Jason Dinesen, EA, LPA

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Whether you’re preparing Forms 1099 for the first time or you’re a seasoned pro, the reporting landscape continues to shift—and the IRS is paying close attention. Penalties for even small mistakes are on the rise, and compliance deadlines are tighter than ever.

This power-packed webinar—offered in both 60- and 100-minute formats—equips tax professionals, accountants, and finance teams with the essential tools and best practices to stay compliant, accurate, and audit-ready when issuing Form 1099-MISC and other information returns.

You’ll get up to speed on the latest IRS changes, including the safe harbor for de minimis errors, new filing and furnishing deadlines, and the expanded use of TIN solicitation and verification tools. We’ll demystify “B” Notices, backup withholding, and reasonable cause standards, and explore the practical steps to correct errors before they lead to costly penalties.

Learning Outcomes

  • Learn what’s new for Form 1099-MISC and related filings for the current tax year
  • Understand the difference between reportable and non-reportable payments
  • Identify when and how to issue “B” Notices and handle TIN mismatches
  • Master the art of backup withholding: when it applies and how to manage it
  • Implement best practices for W-9 collection and TIN solicitation
  • Discover how to correct 1099 errors the right way—and avoid IRS scrutiny
  • Learn what constitutes “reasonable cause” to defend against penalties
  • Access IRS resources and tools to streamline compliance

Why You Should Attend

The IRS continues to ramp up enforcement and scrutiny of information returns, making Form 1099 compliance more important than ever. With penalties on the rise and new reporting rules in effect, this webinar gives you the confidence to avoid costly errors, implement effective due diligence processes, and provide value-added services to clients. Whether you’re in accounting, AP, tax prep, or compliance—this session offers the critical insights and practical tools you need.

Who Should Attend

  • Accountants
  • CPAs
  • Enrolled agents
  • Bookkeepers
  • Tax preparers
  • AP professionals
  • Attorneys

 

Note

After the live event, there will be a Q&A session where you can ask a question directly to our expert speaker. They will provide a clear and understandable response to help you better understand the topic.

Note: After completing your webinar purchase, please check your spam/junk folder in your email for the webinar joining link, which will be sent after the confirmation email.

Speaker

Jason Dinesen, EA, LPA, is a nationally recognized tax expert, educator, and speaker with over two decades of experience in individual and small business taxation. Known for his sharp insights and practical approach, Jason has presented hundreds of continuing education webinars and seminars on topics ranging from Form 1099 to corporate taxation and ethics.

He has educated over 200,000 professionals through engaging, real-world training sessions and is frequently featured in podcasts and tax industry media. As a former news reporter turned “tax nerd,” Jason brings a unique storytelling style to complex compliance topics—making them approachable, relevant, and memorable.

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