Episodes

As 2025 comes to a close, this special year-end episode of Information Return Intelligence looks back at the most important developments in information return reporting—especially those affecting accounts payable and compliance teams. We walk chronologically through the year, highlighting regulatory changes, IRS guidance, legislation, and draft forms that will shape reporting obligations in 2025 and beyond. Key topics covered include: January regulations on digital and cloud transactions Final...

This week, we lead into Christmas on a lighter note. An animated cartoon Jason created, called "A 1099 Christmas Carol." If you want to see the video, head to our YouTube page. https://www.youtube.com/@InformationReturnIntelligence Credits: A 1099 Christmas Carol Written by: Jason Dinesen Animated by: Jason Dinesen in Runway (www.runwayml.com) Music: Joy to the World (Instrumental) by Matthew L. Fisher – license purchased by Dinesen Media Ventures, LLC through Audiio (www.audiio.co...

Today’s episode breaks down the fast-changing world of electronic filing for information returns — including major updates to FIRE, IRIS, and Form 1042/1042-S e-filing. We cover: 🔹 The 10-form e-file threshold under the Taxpayer First Act 🔹 How W-2s fit into the e-file mandate (and why it’s not an “IRS rule”) 🔹 The scheduled shutdown of the FIRE system in December 2026 🔹 What that shutdown really means for the 2025 filing season 🔹 When and how to transition to IRIS 🔹 Limitations inside IRIS — ...

In this episode, Jason breaks down one of the trickiest parts of compliance: state 1099 filing rules. Every state has its own requirements — and some of them will surprise you. (Looking at you, New York and Illinois!) What You’ll Learn Why the state boxes on a 1099 don’t fulfill your state filing obligations How to determine which states you need to file in Why contractor location (and where the work is performed) matters How state backup withholding rules differ — especially California’s W...

In this episode of Information Return Intelligence, Jason revisits last week’s big topic: the new overtime deduction created by the One Big Beautiful Bill (OBBB). After initially believing there was no scenario where qualifying FLSA overtime could ever appear on a 1099… Jason discovered there is a rare situation where it actually can. Join Jason as he breaks down: What counts as “qualifying overtime” under the OBBB Why Section 7 of the FLSA is the key to the deduction Why most overtime won’t...