Information Return Intelligence

The $600 reporting threshold has been part of the information-reporting landscape for decades — but where did it actually come from, and why did it stay frozen in time for so long? In this episode of Information Return Intelligence , Jason Dinesen digs into the history of the $600 threshold just as it prepares to disappear. Starting in 2026, the long-standing $600 amount under IRC §6041 will be re...

In this episode of Information Return Intelligence , Jason Dinesen goes back to one of the most fundamental—and most commonly misunderstood—questions in information reporting: how do you know when you’ve crossed the 1099 reporting threshold? With the familiar $600 threshold increasing to $2,000 for many payments starting in 2026 , understanding how amounts are counted is more important than ever....

In this week’s What’s New episode of Information Return Intelligence , Jason Dinesen provides a concise mid-January update as the 1099 filing season gets underway. With electronic filing officially open and few last-minute surprises, this episode focuses on the key system and compliance issues filers should be aware of right now. Key topics covered: 1099 e-Filing is Open Electronic filing opened J...

In this episode of Information Return Intelligence, host Jason Dinesen is joined by Deborah Richardson, nationally recognized accounts payable consultant, speaker, and trainer, to break down a draft revision of Form W-9 that could have significant implications for vendor setup and 1099 compliance. While the IRS has not yet finalized the form, the proposed change is more consequential than it may a...

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...

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) b...

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 r...

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 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 overt...

The IRS has issued new guidance on reporting tips and overtime , and while these topics usually live in the W-2 world, they now have implications for 1099 filers as well. In this episode, Jason Dinesen — The 1099 Guy — explains how the Big Beautiful Bill created a new personal tax deduction for qualifying tips and qualifying overtime, and how upcoming changes to Form 1099-NEC and 1099-MISC will re...

The IRS quietly released a draft Form W-9 in mid-September — and one proposed change could have a major impact on how businesses collect taxpayer identification numbers from sole proprietors and single-member LLCs. In this episode, Jason Dinesen — The 1099 Guy — breaks down what’s in the draft, why the change matters, and what AP, procurement, and vendor onboarding teams should do now (and not do...

The $600 reporting threshold for 1099s has been with us since 1954 — older than Elvis and untouched by inflation. But starting with 2026 payments, it’s finally changing to $2,000 and will be indexed going forward. In this episode, host Jason Dinesen — The 1099 Guy — explains why the threshold lasted so long, what’s changing under the Big Beautiful Bill, and what steps accounting and finance profes...