Episodes

The third quarter of 2026 brought plenty of developments in the world of information reporting. In this episode, Jason breaks down what 1099 professionals need to know from July, August and September. You’ll learn about the upcoming shutdown of the FIRE system and transition to IRIS, what to watch for during CP2100 and B Notice season, the status of the long-awaited Form W-9 update, changes to Forms 1099-NEC and 1099-MISC, new information returns, updated 1099-K backup withholding rules, and ot...

It’s “B” Notice season — and this week, we’re getting very specific about envelopes. When a payer receives a CP2100 notice from the IRS, one of the potential next steps is sending a “B” Notice to the payee. And the IRS has some very particular requirements for how that notice must be sent. Publication 1281 says the outer mailing envelope must include the words “Important Tax Return Document Enclosed” or “Important Tax Return Information Enclosed.” But what exactly does “on the outer mailing e...

Just like football season, CP2100 letter season has arrived. A CP2100 letter means the IRS found a problem when trying to match a name and taxpayer identification number (TIN) reported on a 1099 with the information in its records. So what should you do when one shows up? In this episode of Information Return Intelligence, Jason Dinesen walks through the CP2100 process from start to finish, including: Why the IRS sends CP2100 lettersWhy you should review your own records before contacting the...

FIRE is going away. If you haven't figured out what you're doing next, now is the time. In the latest episode of Information Return Intelligence, Jason Dinesen looks ahead to the end of the FIRE system and explains why businesses shouldn't wait until January to make the move to IRIS—or to find a third-party filing provider. For organizations planning to file directly through IRIS, getting started involves more than simply creating an account. You'll need to determine whether you're using the ...

This week on Information Return Intelligence, we wrap up our three-part series on Form 1099-K by tackling a common question: Why not just issue a Form 1099-NEC and avoid all the complexity? The answer is simple: because the regulations say not to. Here are the other parts: Part 1 Part 2 When 1099-K Takes Priority Suppose you pay a contractor $1,000 by check or ACH in April and another $1,000 through a payment app in July. If the July payment is made in a way that transfers the reporting oblig...

The IRS has announced the official shutdown date for the Filing Information Returns Electronically (FIRE) system: 3:00 p.m. Eastern Time on November 19, 2026. We knew this day was coming. Now we know exactly when — right down to the hour. A Little FIRE History FIRE has been around since 1986 and, for most of its existence, was the primary IRS intake system for electronically filed information returns, including Forms 1099 and 1042-S. That began to change with the introduction of the Informati...

The IRS has released Revenue Procedure 2026-18, its annual guidance on substitute forms — and despite the somewhat obscure name, the rules can affect virtually anyone responsible for filing or furnishing Forms 1099. What Is a Substitute Form? A substitute form is an information return produced in a format other than the official form supplied by the IRS. The IRS publishes detailed specifications governing how these forms must look and what information they must contain. For organizations that...

In this week’s Information Return Intelligence, it’s time for another round of Ask the Experts. I dig into four real-world questions that show how quickly information reporting can go from “this should be easy” to “well, actually…” We cover: B Notices: Publication 1281 says the outer mailing envelope must be marked “Important Tax Information Enclosed” or “Important Tax Return Document Enclosed.” Does having those words visible through a window envelope count?Wage garnishments: Are payments se...

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 ...