Episodes

The IRS has released a new draft of Form W-9—and this one brings welcome relief for accounts payable teams. In this episode, Jason breaks down the May 4 draft update and explains why the IRS’s decision to remove the proposed restriction on sole proprietors using EINs is a big deal. That controversial change would have created a massive compliance burden, forcing companies to re-solicit W-9s and revalidate vendor records at scale. For now, that headache is off the table. Jason also walks throug...

This week on Information Return Intelligence, we break down one of the most overlooked areas of 1099 compliance: electronic delivery to recipients. Most organizations are used to thinking about e-filing with the IRS—but what about actually getting the form to the recipient? If you’re emailing PDFs of 1099s (and let’s be honest, most people are), there’s a good chance you’re not fully compliant with IRS rules. In this episode, Jason walks through: Why 1099 e-delivery rules are tied to W-2 regu...

This week on Information Return Intelligence, Jason Dinesen breaks down a developing story from the Treasury Department and IRS that could significantly impact how organizations deliver 1099s—and other information returns—to recipients. The Treasury has issued proposed regulations to simplify electronic delivery (eDelivery) for Form 1099-DA (digital assets), while the IRS is simultaneously requesting public comments on expanding those changes to other forms, including Form 1099-B—and potentiall...

In this recurring feature, we tackle various questions that people have submitted recently about 1099s and 1042-S. This episode: --The draft of a new W-9: can you use it? --Is FIRE really being shut down? What about file formatting in IRIS? --Does the credit card exception apply to Form 1042-S? --What if a vendor checks box 3b on the W-9?

This episode recaps what happened in the 1099 and 1042-S world in the first quarter of 2026. Highlights: --Still no new W-9, but draft W-9 instructions released --Do Native American tribes need to issue 1099s? --FIRE shutdown becomes clearer --2026 drafts of 1099-NEC and 1099-MISC --Treasury Department seeks comment on providing forms to recipients electronically --And more!

The IRS dropped another round of draft 2026 forms on March 27th — updated versions of the 1099-NEC and 1099-MISC — and we still don't have a final version, which is notably late compared to prior years. Jason walks through what's changed in the latest drafts, including the new boxes for reporting tips and overtime pay, and a cosmetic redesign of the name and address fields that's probably not a big deal but worth keeping an eye on. The bigger conversation this week is the why behind those new b...

The IRS has been signaling for months that the FIRE system — one of its two electronic intake systems for information returns — is on its way out. But earlier 2026 drafts of Publication 1099 left some wiggle room in the language. The March 2026 draft doesn't. Jason Dinesen walks through exactly what the updated publication says, explains what FIRE and IRIS actually are and why the distinction matters, and lays out your practical e-filing options as the end-of-2026 shutdown approaches. Whether yo...

A followup to last week's episode, as the IRS did end up releasing an efile waiver procedure for Form 1042. But just because the procedure exists doesn't mean you should use it. To request a waiver, you'll need to demonstrate hardship, document the steps you've already taken to comply, provide a cost computation, outline your plan to e-file in the future, and have an authorized officer sign under penalty of perjury. Requests go to the IRS by fax or mail, and here's the catch: the IRS won't se...

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...