2026 Smart 1099 Reporting Practices & Updates

(2 Credit Hours of Federal Tax Law)

Instant Access
$54.97

Recorded on January 29, 2026, this course delivers updated, practical guidance on information return reporting affecting both 2025 and 2026. Topics include revised dollar thresholds, IRS system changes related to IRIS and FIRE, and expanded treatment of digital and cloud transactions, including SaaS, under final and proposed Treasury regulations.

Participants will also review enhanced Form 1042-S guidance, including sourcing of services, cross-border payment scenarios, and the lack of common reporting exceptions. The course reflects draft W-9 updates as of January 29, 2026, including proposed SSN-only requirements for sole proprietors and potential W-9 re-solicitation considerations.

Additional instruction covers updated electronic delivery rules for 1099 recipient statements and expanded state filing guidance, including risks associated with reliance on IRS Publication 1220 for combined federal/state filing.

Learning Objectives

After completing this course, participants will be able to:

  • Apply updated information return rules for 2025 and 2026
  • Explain how IRIS replaces FIRE and affects filing processes
  • Distinguish between digital transactions and cloud transactions
  • Identify Form 1042-S obligations for cross-border service payments
  • Evaluate draft W-9 changes and related compliance impacts
  • Apply electronic delivery consent, format, and notification rules
  • Recognize state filing and CF/SF participation risks

This course counts for 2 Hours of Federal Tax Law for IRS Continuing Education. 

About the Presenter:

Jason Dinesen (EA, LPA) is a tax nerd, entrepreneur, tax expert, and a well-known presenter of continuing education courses. 

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 dozens of webinars on Form 1099 (for 10 years on this subject!), marriage in the tax code, tax updates, the new Form W-4, payroll updates, filing status, tax credits, corporation and partnership taxation, and other issues relating to the modern-day setting.