Information Return Intelligence
Your weekly briefing on 1099s, 1042-S, and everything related to information forms.
Episodes
37 episodes
Episode 35 -- Second Quarter Form 1099 Roundup
Q2 2026 Roundup: W-9 Drafts, Backup Withholding, IRIS Updates & MoreThe second quarter of 2026 brought a surprising number of developments in the information reporting world, and in this episode of Information Return Intelligence, J...
Episode 34: Form 1099-K, Part 2 -- Why the $600 Threshold Was Reversed
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 re...
Episode 34: Form 1099-K, Part 2 -- Why the $600 Threshold Was Reversed
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 re...
Episode 34: Form 1099-K, Part 2 -- Why the $600 Threshold Was Reversed
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.Fin...
Episode 33: IRS Releases 2026 Version of 1099-NEC and 1099-MISC
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, particu...
Episode 32: 1099-K, Part 1: Understanding the Rules and the Reporting Gap
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...
Episode 31: Treasury Aligns Backup Withholding with New 1099 Reporting Thresholds
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 reportin...
Episode 30: The Kwong Case -- A Big Tax Deal, But What About Information Returns?
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 ep...
Episode 29: Powwows, Prizes, and 1099s: Lessons from a 2026 IRS Ruling
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 inv...
Episode 28: IOFM Conference Takeaways: Anxiety, Complexity, and AI
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 profes...
Episode 27: Ask the Experts, Volume 2
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 coll...
Episode 26: Latest W-9 Draft -- IRS Reverses Course on Sole Proprietor EIN Rule
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 o...
Episode 25: E-Delivery Rules for 1099s: Why Emailing PDFs Isn’t So Simple
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 actual...
Episode 24: Treasury Department Seeks Public Input on Easing E-Delivery Rules
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....
Episode 23: Ask the Expert, Volume 1
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 formatt...
Episode 22: Roundup of Top Information Return Happenings in the First Quarter
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 becom...
Episode 21: 2026 Form 1099-NEC and 1099-MISC Drafts: New Boxes, New Questions
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...
Episode 20: Goodbye FIRE, Hello IRIS: What E-Filers of 1099s Need to Know
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...
Episode 19: You Can Now Request a Form 1042 E-File Waiver — Should You?
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...
Episode 18: Can't E-File Form 1042? Skip the Waiver — Do This Instead
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 ...
Episode 17: What's Due in March (And Why Form 1042 Filers Should File an Extension Now)
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 b...
Episode 16: Single-Member LLCs and the W-9: Whose TIN Goes on the Form?
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 ...
Episode 15: Fixing 1099 Errors & Filing Corrections
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 program...
Episode 14: 5 Ways to Make 1099 Filing Even Smoother Next Year
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 or...
Episode 13: A Look at the Drafts of 1099-NEC and 1099-MISC
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...