Information Return Year-in-Review II

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Thursday, December 17, 2026 | 2:00PM-3:45PM Eastern Time

Some “what’s new” items relating to Form 1099 and Form 1042-S are well-known, such as the change to the dollar threshold, or the FIRE system being shut down. Some changes are not as well-known. The latter are the ones we’ll cover in this session, including: Form 1042 electronic filing and IRS e-file waivers; the United States Postal Service changing its postmark rules; Treasury Department regulations on digital transactions, such as software as a service; a court case about repayment of previously taxable income (with a 1099 lesson); multiple court cases involving lawsuit settlement taxation (with a 1099 lesson); IRS private letter rulings on Native American tribes issuing 1099s and on how to report gambling winnings of nonresident aliens. This session will open your eyes to the fact that there is a lot going on with these forms, beyond the things that grab the headlines.

Learning Objectives

  1. Understand why Form 1042 e-filing can be problematic
  2. Understand new postmark rules at the postal service
  3. Identify when and how to apply the new regulations on SaaS
  4. Understand how to deal with repayment of amounts previously on a 1099
  5. Understand how lawsuit settlements work
  6. Understand reporting requirements on tribes
  7. Understand how to report gambling winnings to a nonresident alien

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Featured Speaker

Jason Dinesen

Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason is the founder of Dinesen Tax & Accounting, P.C. and Dinesen Tax Advisory, LLC in the tax and accounting world. He also is founder of 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.


Continuing education credits available!

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Receive 2 CEUs toward maintaining a certification with IOFM! IOFM's premier certification programs are designed to establish standards for the industry and recognize financial operations professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the body of knowledge in their profession. Additional rules may apply, depending on your certification. See full guidelines here. 

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IOFM is committed to accessibility. Disability-related accommodation requests for the live event (such as providing live captioning) should be sent to [email protected] by close of business the day before the live webinar. A captioned recording of this webinar can be made available upon request to [email protected].


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