Episodes

Form 1042 is due March 16th, and e-filing it is more complicated than you might expect. Jason Dinesen explains why Form 1042 uses the IRS's MeF system instead of IRIS or FIRE, what the e-file mandate means for your organization, and why filing a Form 7004 extension is likely your best move if you don't have a clear path to electronic filing. Sponsored by IOFM — iofm.com.

March 2026 has several information return deadlines you don't want to miss. Jason Dinesen covers the March 16th due dates for Form 1042-S and Form 1042, explains the e-filing complications with Form 1042 and why an extension (Form 7004) might be the smart play, and flags the March 31st Form 1095-B deadline that catches small businesses off guard. Extension forms 8809 and 15397 are also covered for anyone who needs extra time.

Single-member LLCs and Form W-9 continue to cause confusion — especially when it comes to which taxpayer identification number (TIN) should be provided. In this episode of Information Return Intelligence, Jason Dinesen tackles a common (and frustrating) issue: single-member LLCs taxed as disregarded entities providing the LLC’s EIN instead of the owner’s Social Security number (or the owner’s EIN, if they have one personally). Accounts payable professionals often push back when vendors submit ...

You filed your 1099s. Now you found a mistake. What do you do? In this episode of Information Return Intelligence, I break down: ✅ Why we file 1099s in the first place (hint: it’s about IRS matching programs and tax compliance)✅ How the IRS actually uses the data you submit✅ What kinds of errors matter (and which ones don’t)✅ When you are required to file a correction✅ The key August 1 deadline that can help you avoid penalties✅ The de minimis dollar error rule ($100 / $25 for backup withhold...

he January 31 deadline for Form 1099-NEC filing has passed—but that doesn’t mean it’s time to stop thinking about information returns. In this episode of Information Return Intelligence, Jason Dinesen breaks down five practical things organizations should do right now to strengthen their 1099 and information return process for the rest of 2026 and beyond. If you only do one thing, Jason explains what it should be—and why it solves more 1099 problems than almost anything else. In this episode,...

In this episode of Information Return Intelligence, I break down the draft 2026 versions of Forms 1099-NEC and 1099-MISC and explain what’s really going on with the new boxes for tips and overtime. These changes are tied to the Big Beautiful Bill and the new above-the-line deduction for qualifying tips and qualifying overtime on individual tax returns. While this feels like a payroll issue (and most of the time, it is), there are some important 1099 implications that AP and tax teams can’t igno...

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 replaced by a $2,000 threshold, indexed for inflation — a change finalized in 2025 legislation. Jason...

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. Key topics covered: What “Crossing the Threshold” Really MeansReporting is based on the cash method ...

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 OpenElectronic filing opened January 6. Both FIRE and IRIS systems are live for the season. IRIS Expansion: Form 1042 Now Suppor...

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 appear at first glance—particularly for individuals and sole proprietors. 🔍 The Key Proposed Change...

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...

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 reflect this. Jason also breaks down the difference between voluntary and non-voluntary tips, why most...

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 yet). This is a big one: the IRS is proposing that sole proprietors would no longer be allowed to p...

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 professionals should take to prepare. You’ll learn: The history and legal background of the $600 rule H...