Recorded on January 29, 2026, this course provides practical instruction on evolving 1099 and information return requirements affecting both 2025 and 2026 filings. Participants will review key IRS updates, including the transition from FIRE to IRIS, revised dollar thresholds, and expanded guidance on digital and cloud transactions, including SaaS, under final and proposed Treasury regulations.
The course delivers enhanced coverage of Form 1042-S for cross-border payments, emphasizing sourcing of services, the absence of dollar thresholds or common exceptions, and the increased risks created by cloud-based transactions. Participants will also examine draft W-9 changes as of January 29, 2026, including proposed SSN-only rules for sole proprietors and potential re-solicitation of W-9s.
Additional topics include updated electronic delivery requirements for 1099 recipient statements and expanded state filing guidance, including new cautions regarding reliance on IRS Publication 1220 for combined federal/state filing participation.
Learning Objectives
After completing this course, participants will be able to:
- Apply updated 1099-NEC and 1099-MISC rules for 2025 and 2026
- Explain the IRS transition from FIRE to IRIS and its impact on filing workflows
- Distinguish digital transactions from cloud transactions under Treasury regulations
- Apply final regulations treating cloud transactions as services
- Identify when Form 1042-S applies and why common exceptions do not apply
- Evaluate draft W-9 changes and potential W-9 re-solicitation requirements
- Implement updated electronic delivery consent, format, and notification rules
- Identify state filing risks, including limitations of IRS Publication 1220
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.
