Information Return Intelligence
Your weekly briefing on Form 1099, Form 1042-S, Form W-9 and anything else under the heading of an information return.
Recent Episodes
48
Oct. 6, 2026
Episode 48: 3rd Quarter 2026 Roundup
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
47
Sept. 29, 2026
Episode 47: Does the B Notice Wording Really Have to Be on the Envelope?
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...
46
Sept. 22, 2026
Episode 46: It’s CP2100 Letter Season!
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...
45
Sept. 15, 2026
Episode 45: Want to Use IRIS? Start the Process Now
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 ...
44
Sept. 8, 2026
Episode 44: Form 1099-K Part 3
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
43
Sept. 1, 2026
Episode 43: FIRE, Extinguished
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
Recent Blog Posts
Sept. 23, 2026
CP2100 Season is Here!
It’s that time of year when CP2100 letters will begin arriving. This article will cover what a recipient of such a letter should do. What is It? To understand CP2100 letters, we need to start at the start. Your organization files a 1099 with the I…
Sept. 16, 2026
Want to Use IRIS? Start Now
If you haven't started your move from FIRE to IRIS yet, you'll want to start as soon as possible. Backstory The IRS has maintained two systems for e-filing of 1099s – FIRE and IRIS. FIRE is going out of service at 3 pm Eastern time on November 19,…
Sept. 8, 2026
Form 1099-K, Part 3
This is the third and final installment in our 1099-K series. In prior parts, we touched on how, when paying expenses that could be subject to 1099-K reporting, you don't issue a 1099. Usually we're talking about contract labor/1099-NEC, but it cou…
About the Host
Jason Dinesen
Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason prepares some tax returns each year, but spends most of his professional time teaching on various tax-related topics -- with 1099s being the one everyone comes back to over and over.
He's also the founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals to podcast production to radio and journalism content.
Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics.
Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe's in West Des Moines, Iowa.
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