Information Return Intelligence
Your weekly briefing on 1099s, 1042-S, and everything related to information forms.
Episodes
27 episodes
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...
Episode 12: A History of the $600 Threshold
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
Episode 11: Crossing the $600/$2,000 Threshold -- How Do You Know?
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 thre...
Episode 10: What's New with Information Forms, January 2026
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 surpri...
Episode 9: Proposed Changes to Form W-9: What AP Teams Need to Know Now
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 signific...
Episode 8: 1099 and 1042-S Year-in-Review
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 team...
Episode 7: A 1099 Christmas Carol
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.
Episode 6: E-Filing Updates
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 t...
State 1099 Filing Rules Explained
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!)W...
Overtime on a 1099? Rare But Possible
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 ...