Episodes

The IRS recently released new FAQs dealing with the deduction for qualified overtime compensation. At first glance, this would seem to have nothing to do with 1099s. Overtime is generally an employee issue, which means W-2 reporting. But buried in the FAQs is an interesting question: When would qualified overtime compensation be reported on Form 1099-MISC or 1099-NEC instead of Form W-2? Yes, that can happen. The issue comes down to worker classification. The Department of Labor and the...

If your organization pays a legal settlement, and part of that settlement goes directly to the plaintiff's attorney, should that attorney portion be included on the plaintiff's Form 1099-MISC? The answer is yes. In this week's episode of Information Return Intelligence, Jason reviews the recent Eiler v. Commissioner decision, which reinforces a long-standing principle of tax law: the plaintiff is generally taxed on the entire taxable settlement, including amounts paid directly to their attorne...

Every year, there's a little-known deadline that can save 1099 filers from costly IRS penalties. In this episode of Information Return Intelligence, Jason explains why August 3, 2026 (normally August 1) is such an important date for correcting information returns. Learn how the IRS treats errors on timely filed forms, how many corrections you can make without penalty, and which mistakes don't require correction at all. Jason also discusses the de minimis error rules, why intention...

Have a tricky 1099 question? You're not alone. In this fourth installment of our Ask the Expert series, Jason Dinesen answers real-world questions submitted by accounts payable and tax professionals. These are the kinds of scenarios that don't always have obvious answers—but they're exactly the situations finance teams encounter every day. This episode covers: When credit card payments shift reporting from Form 1099 to Form 1099-K—and why the same rule doesn't apply to Form 1042-SWhethe...

The IRS has introduced a new feature that allows businesses to instantly download verification of their Employer Identification Number (EIN) through their online Business Tax Account. It's a welcome improvement—but does it satisfy the documentation requirements for a second B Notice after receiving a CP2100? In this episode of Information Return Intelligence, Jason Dinesen examines the new online EIN verification process, explains how the CP2100 and B Notice procedures work, and answers the pra...

Q2 2026 Roundup: W-9 Drafts, Backup Withholding, IRIS Updates & More The second quarter of 2026 brought a surprising number of developments in the information reporting world, and in this episode of Information Return Intelligence, Jason Dinesen breaks down the biggest stories that matter to 1099 professionals. Topics include the latest draft Form W-9 and the IRS's reversal on the proposed EIN restriction for sole proprietors, proposed regulations updating backup withholding thresholds,...

Why did Congress try to lower the Form 1099-K reporting threshold to $600—and why did it eventually reverse course? In Part 2 of our Form 1099-K series (find Part 1 here: https://youtu.be/NDv7rk0m6Ws), Jason Dinesen examines the reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The history of Form 1099-K The American Rescue Plan Common misconceptions about Venmo reporting IRS enforce...

Why did Congress try to lower the Form 1099-K reporting threshold to $600—and why did it eventually reverse course? In Part 2 of our Form 1099-K series (find Part 1 here: https://youtu.be/NDv7rk0m6Ws), Jason Dinesen examines the reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The history of Form 1099-K The American Rescue Plan Common misconceptions about Venmo reporting IRS enforce...

In Part 2 of our three-part series on Form 1099-K, we move beyond the mechanics of the form and examine one of the biggest controversies in information reporting: the proposal to lower the Form 1099-K reporting threshold to just $600. Find Part 1 here. Why did Congress originally push for the change? What was it hoping to accomplish? And why did lawmakers ultimately reverse course and restore the original $20,000 and 200-transaction threshold? In this episode, Jason explores the policy goals ...

In this episode of Information Return Intelligence, we discuss the recent updates to the 1099 NEC and Miscellaneous forms for 2026. Most of the episode is focused on tips and overtime, and we dive into the implications of these changes, particularly regarding worker classification and the reporting of tips for contractors.

Form 1099-K has become one of the most misunderstood information returns in the tax world. Between shifting reporting thresholds, IRS delays, and years of media coverage, many businesses and tax professionals know the form exists—but aren't entirely sure when it applies. In Part 1 of this three-part series, Jason Dinesen breaks down the basics of Form 1099-K, including the difference between payment card transactions and third-party settlement organizations such as PayPal, Venmo, and Etsy. He e...

The Treasury Department has released proposed regulations that would update the backup withholding rules to align with the new information reporting thresholds created by the One Big Beautiful Bill. For decades, the familiar $600 reporting threshold under Sections 6041 and 6041A remained unchanged. Beginning in 2026, that threshold increases to $2,000 and will be adjusted annually for inflation. However, Treasury regulations under Section 3406 still reference the old $600 amount for backup with...

The recent Kwong case has generated significant discussion in the tax community, particularly regarding whether taxpayers may be entitled to refunds of certain IRS penalties assessed during the COVID-19 pandemic. In this episode of Information Return Intelligence, Jason Dinesen examines the case from a different perspective: What does Kwong mean for information reporting professionals? Topics include: An overview of the Kwong decision and why it matters How COVID-era deadline suspensions fac...

In this episode of Information Return Intelligence, Jason breaks down a recent IRS private letter ruling that answers a deceptively simple question: Do tax-exempt organizations still have 1099 reporting obligations? The ruling involved a Native American tribe that awarded prize money at a powwow and questioned whether those payments required Form 1099 reporting. The tribe made three key arguments: They are not subject to income tax They are not a “person” under the tax code The activity was n...

At this year’s IOFM Spring Conference in Orlando, one theme kept surfacing over and over again: uncertainty. In this episode of Information Return Intelligence, Jason shares his biggest takeaways from conversations with AP professionals, compliance teams, and attendees across the conference floor. While the sessions themselves were valuable, the real insights came from listening to the concerns people are facing every day in the information reporting world. Three major themes emerged: • Growi...

It's another Ask the Experts feature. The questions addressed this time: --What if you have to re-issue a check to the payee because they lost it, and it's the next year? Do you need to correct anything or issue new 1099s? --Is a collection agency associated with a medical facility providing a "medical service" reportable on 1099-MISC (box 6) --Is a non-cash amount, such as a book, given to a contractor considered contract labor? --How do you handle a legal settlement where interest payments ...

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...