Information Return Intelligence

 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 explains who issues the form, when reporting is required, and why businesses often do not issue Form 1099-NEC when payments are made through certain electronic platforms.The episode also explores one of the biggest compliance issues surrounding 1099-K reporting: the potential reporting gap created by the current threshold of more than 200 transactions and more than $20,000 received through a third-party settlement organization. Through a practical contractor example, Jason illustrates how significant business income can sometimes fall outside both 1099-K and 1099-NEC reporting requirements.Topics covered include:What Form 1099-K reportsPayment card transactions vs. third-party settlement organizationsWhy most bill pay services are not subject to 1099-K reportingWhen businesses should not issue Form 1099-NECThe history of the controversial $600 reporting thresholdHow the One Big Beautiful Bill restored the prior reporting thresholdThe compliance concerns created by the current rulesThis episode lays the groundwork for Parts 2 and 3, where we'll examine the competing viewpoints behind the reporting threshold debate and discuss why reasonable people can disagree on whether lowering the threshold would have improved tax compliance.Information Return Intelligence is powered by IOFM and covers the latest developments in Forms 1099, W-9, 1042-S, backup withholding, e-filing, and information reporting compliance. 

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 withholding purposes. The newly proposed regulations would fix that mismatch by tying the backup withholding trigger directly to the inflation-adjusted reporting threshold in effect each year.In this episode, Jason explains what the proposed regulations do, why they are necessary, and what they mean for accounts payable professionals. You'll also hear a practical walkthrough of when backup withholding is required, how the threshold works in real-world payment scenarios, and a common question about which payments are actually subject to withholding once a payee crosses the reporting threshold.If you handle vendor payments, W-9 compliance, or 1099 reporting, this is an important update to understand as organizations prepare for the coming changes.Key Topics Covered: The new $2,000 information reporting threshold beginning in 2026  Why Treasury needed to update the backup withholding regulations  The relationship between Sections 6041, 6041A, and 3406  When backup withholding is triggered  How to determine which payments are subject to withholding  Practical examples for accounts payable departments Resources: Proposed Treasury Regulations under IRC Section 3406  IRC Sections 6041 and 6041A  One Big Beautiful Bill Act reporting threshold changes Information Return Intelligence is hosted by Jason Dinesen and sponsored by IOFM, the Institute of Finance & Management.

 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 mattersHow COVID-era deadline suspensions factor into the court's rulingWhether Forms 1099 and 1042-S are affectedThe impact (or lack thereof) on information return filing penaltiesBackup withholding deposit penalties and disaster relief rulesWhy Forms 945 and 1042 may present a different analysisThe importance of protective refund claims and the July 10, 2026 deadlineThe appeals process and why the final outcome remains uncertainWhile most commentary on Kwong has focused on individual income tax filings, this episode explores the implications for the information reporting world and helps practitioners understand where potential opportunities—and limitations—may exist.Information Return Intelligence is sponsored by IOFM, the Institute of Finance & Management. Learn more at IOFM.com.#1099 #InformationReporting #TaxCompliance #IRS #Form1099 #Form945 #1042 #BackupWithholding #TaxProfessionals #AccountsPayable #IOFM #TaxNews #TaxUpdates #InformationReturnIntelligence 

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 taxThey are not a “person” under the tax codeThe activity was not a trade or businessThe IRS rejected all three.While private letter rulings only apply to the taxpayer who requested them, they provide valuable insight into how the IRS interprets the law. In this case, the takeaway is clear:Information reporting under IRC §6041 applies broadly—even to tax-exempt entities and activities that are not conducted for profit.Jason walks through:Why being tax-exempt does not eliminate 1099 obligationsHow the IRS defines a “person” under IRC §7701Why “not-for-profit” activities can still trigger reporting requirementsWhat nonprofits, government entities, and similar organizations should take away from this rulingHe also raises an interesting open question:Could the IRS’s reasoning extend beyond tax-exempt entities to other non-profit-motivated activities, such as hobbies?If you work in accounts payable, finance, or compliance, this episode is a reminder that 1099 reporting rules are broader than many organizations assume—and exemptions are narrower than they appear.📌 Key Takeaway:Even if your organization doesn’t pay income tax—or isn’t operating for profit—you may still be required to issue Forms 1099.This episode is sponsored by IOFM, the Institute of Finance and Management. Learn more at IOFM.com.

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:• Growing anxiety around information reporting compliance• Frustration with increasing complexity and constantly changing rules• Confusion and uncertainty surrounding artificial intelligence and AP technologyJason discusses the upcoming transition from the FIRE system to IRIS, the new 1099 reporting thresholds, ongoing worker classification confusion, and why so many professionals feel overwhelmed by overlapping IRS, DOL, and state rules.The episode also explores the current state of AI in the AP and information reporting space — including skepticism about vendor claims, pressure from management to “use AI,” and the challenge of figuring out what many AI products actually do.If you work with 1099s, W-9s, AP compliance, or information reporting in any form, this episode provides a candid look at what your peers are thinking — and worrying about — right now.Sponsored by IOFM, the Institute of Finance & Management.#1099 #AccountsPayable #AP #InformationReporting #IOFM #TaxCompliance #IRIS #ArtificialIntelligence #Finance #1099Guy 

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 are involved?As always, we are sponsored by IOFM, the Institute of Finance and Management. www.iofm.com 

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 through what did change in the draft, including: A new backup withholding exemption code tied to broker and Form 1099-DA reporting  Updated (and much clearer) language around TIN reporting—specifically reinforcing that disregarded entity EINs should not be used Even though the EIN restriction is gone, the IRS is making its expectations more explicit—and that has real implications for how W-9s are completed and reviewed.As always, this is still a draft. Jason closes with practical guidance on what AP professionals should be doing right now (hint: keep using the March 2024 version).If you deal with W-9s, vendor onboarding, or 1099 compliance, this is a must-listen update.

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 regulationsWhat the IRS actually says about furnishing statements electronicallyThe three key requirements: consent, format, and notificationWhy a simple “sure, email it to me” isn’t enoughHow major e-filing platforms handle compliance (and why it matters)The real-world risk of ignoring these rules—even if “everyone else is doing it”The takeaway? This isn’t a gray area. The rules exist, they’re detailed, and they’re enforceable—even if they’re widely ignored.If your current process involves emailing 1099 PDFs without a formal consent workflow, this episode will make you rethink that approach.Key Topics CoveredIRS Publication 1099 and electronic furnishing rulesReg. §31.6051-1 and its application to 1099sRecipient consent requirements (and why they’re more complex than expected)Substitute statement formatting (Pub. 1179)Website posting and notification requirementsPractical compliance strategies for AP teams and tax professionalsWho Should ListenAccounts Payable professionalsTax practitioners and accountantsAnyone responsible for issuing Forms 1099 or W-2Organizations using (or considering) electronic delivery methodsAbout the ShowInformation Return Intelligence is a fast-moving weekly podcast focused on Forms 1099, W-9, 1042-S, and everything in the world of information reporting—brought to you by IOFM.

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 potentially all 1099s.But here’s the bigger issue:Most organizations don’t realize that emailing a PDF of a 1099 isn’t automatically compliant.Jason walks through:What “eDelivery” actually means under current IRS regulationsThe often-overlooked consent requirementsWhy the rules are considered “draconian”What changes may be coming—and why they matter even if you don’t issue 1099-DA or 1099-B📅 Public comments are open until May 23—this could be the beginning of major changes to how information returns are delivered.👉 Next week: A deeper dive into the actual compliance requirements and what organizations should (and shouldn’t) be doing today.Sponsored by IOFM (Institute of Finance & Management)Learn more: https://www.iofm.com

 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 boxes: tips and overtime deductions are now available to workers on their personal returns, which means employers and payers need to break that information out on the forms they issue. For most listeners, that's a W-2 story — but Jason explains the narrow scenario where overtime or tips could legitimately land on a 1099, including the unusual situation where a worker is classified as an employee under the FLSA but treated as a contractor by the IRS.Information Return Intelligence is sponsored by IOFM.

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 your organization files directly or through a third-party vendor, now is the time to get ready.

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 send confirmation letters for 2025 waivers, so if your request is denied, you may not hear about it. The stronger move? If you filed an extension before the March 17 deadline, use that six-month runway to get an e-filing solution in place. 

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 a Form 7004 extension is likely your best move if you don't have a clear path to electronic filing.Sponsored by IOFM — iofm.com.

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 be the smart play, and flags the March 31st Form 1095-B deadline that catches small businesses off guard. Extension forms 8809 and 15397 are also covered for anyone who needs extra time.

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 common (and frustrating) issue: single-member LLCs taxed as disregarded entities providing the LLC’s EIN instead of the owner’s Social Security number (or the owner’s EIN, if they have one personally).Accounts payable professionals often push back when vendors submit the “wrong” number — only to hear, “My accountant told me to use the LLC’s EIN.”So who’s right?Jason walks through:Why 1099s exist (tax compliance and IRS matching)The concept of the beneficial owner in information reportingWhat “disregarded entity” actually meansExactly what the current W-9 instructions say (page references included)Why this issue isn’t open to interpretationWhat the new draft W-9 proposes — and what it would changeThis episode is a practical, instruction-based breakdown of an issue that continues to create friction between vendors, AP departments, and accountants.If you deal with W-9 compliance, this is one you’ll want to share.Shorter Version (YouTube / Podcast Apps)Single-member LLCs taxed as disregarded entities are supposed to provide the owner’s SSN (or the owner’s EIN if they have one personally) — not the LLC’s EIN.So why do so many vendors submit the LLC’s number?In this episode, Jason walks through the W-9 instructions, explains the concept of beneficial ownership, and breaks down what the IRS actually requires — plus a quick update on the draft W-9 that could change the rules.Clear. Direct. No guesswork.

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 programs and tax compliance)✅ How the IRS actually uses the data you submit✅ What kinds of errors matter (and which ones don’t)✅ When you are required to file a correction✅ The key August 1 deadline that can help you avoid penalties✅ The de minimis dollar error rule ($100 / $25 for backup withholding)✅ Why first name and address errors generally don’t trigger penaltiesRemember: the IRS computer matching system primarily keys off the last name/business name and TIN, along with the dollar amount Information Return Intelligence…. If those are wrong, you may have a problem. If they’re not? You may not need to panic.If you discover an error, fix it. In most cases, correcting by August 1 keeps you penalty-free — especially if you’re correcting 10 or fewer forms.This episode is practical, tactical, and designed for AP professionals, controllers, and anyone living in the information return world.🎧 Listen weekly for fast, focused updates on:1099-NEC & 1099-MISC1042-SBackup withholdingCP2100 letters & B-NoticesIRS matching programsAnd everything else in the information return ecosystemIf you work with 1099s, this podcast is for you.— Jason Dinesen

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 organizations should do right now to strengthen their 1099 and information return process for the rest of 2026 and beyond.If you only do one thing, Jason explains what it should be—and why it solves more 1099 problems than almost anything else.In this episode, we cover:Why Form W-9 is your best friend in 1099 complianceHow new Treasury regulations treat cloud transactions (including SaaS)What to review in your 1099 e-filing process, including FIRE vs. IRISCommon pain points with state 1099 filings and how to manage themWhy written procedures matter—for efficiency and penalty protectionThis episode is ideal for:AP professionalsTax professionalsPayroll and compliance teamsAnyone responsible for issuing Forms 1099 or 1042-SWhether you’re cleaning up after filing season or planning ahead for the next one, this episode will help you avoid common mistakes and tighten your compliance process.Subscribe for weekly insights on Forms 1099, 1042-S, W-9s, backup withholding, IRS penalties, and more.

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 tied to the Big Beautiful Bill and the new above-the-line deduction for qualifying tips and qualifying overtime on individual tax returns. While this feels like a payroll issue (and most of the time, it is), there are some important 1099 implications that AP and tax teams can’t ignore.We cover:What’s changing on the draft 2026 1099-NEC and 1099-MISCWhy 2025 reporting is optional, but 2026 will be mandatoryWhen overtime could ever show up on a 1099 (rare, but possible)How tips paid to contractors create new reporting responsibilitiesThe importance of the Treasury’s list of tipped occupationsWhy AP and payroll need to be talking to each other nowIf your organization issues 1099s—or if you’re the person everyone turns to when reporting rules change—this is one of those episodes you’ll want on your radar early.📌 Important note: These forms are still in draft status as of February 3, 2026.Subscribe for weekly updates on 1099s, W-9s, 1042, W-2G, and the weird corners of the information return world.

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, Jason Dinesen digs into the history of the $600 threshold just as it prepares to disappear. Starting in 2026, the long-standing $600 amount under IRC §6041 will be replaced by a $2,000 threshold, indexed for inflation — a change finalized in 2025 legislation.Jason walks listeners through more than a century of tax history, explaining:Why the IRS could never adjust the $600 threshold on its ownHow information reporting didn’t even exist in the original 1913 income tax lawWhen information reporting was first introduced (and at what dollar amount)How the threshold moved up and down throughout the 1930s and 1940sWhy 1954 is the key year for modern information reporting — even though the $600 figure predates itFun historical side notes on early 1099 forms, including the rise, fall, and resurrection of Form 1099-NECIf you’ve ever wondered why $600 became the magic number — or want solid historical context as we move into a new era of reporting thresholds — this episode connects the dots.Key Takeaway: The $600 threshold wasn’t arbitrary — but it also wasn’t inflation-proof. Its replacement marks one of the most meaningful structural changes to information reporting in decades.

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 threshold?With the familiar $600 threshold increasing to $2,000 for many payments starting in 2026, understanding how amounts are counted is more important than ever.Key topics covered:What “Crossing the Threshold” Really MeansReporting is based on the cash method and the calendar year.The trigger is what you actually paid, not what was invoiced.Cash Method Explained (In Plain English)Checks written during the year count—even if the recipient cashes them later.Payments are counted in the year the money leaves your hands.Calendar Year vs. Your Tax Return1099 reporting always follows January 1–December 31.Your organization’s fiscal year or accounting method does not control 1099 reporting.As a result, the amount reported on a 1099 may differ from the deduction shown on your tax return—especially for accrual-method taxpayers.Practical Example WalkthroughAn invoice received in December but paid in January belongs on the following year’s 1099.The same logic applies to year-end invoices paid after December 31.This timing difference affects both:Whether the reporting threshold is met, andWhat dollar amount ultimately appears on the 1099.Bottom line:When determining whether you’ve crossed the $600 threshold (or $2,000 in 2026), and what amount to report:Think cash, not invoices.Think calendar year, not fiscal year.Don’t assume your tax return and your 1099 totals will match—because they often won’t.🎧 Join us again next week for another episode of Information Return Intelligence.

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 surprises, this episode focuses on the key system and compliance issues filers should be aware of right now.Key topics covered:1099 e-Filing is OpenElectronic filing opened January 6.Both FIRE and IRIS systems are live for the season.IRIS Expansion: Form 1042 Now SupportedIRIS can now accept Form 1042 (summary form) for the first time.In prior years, IRIS could not accommodate this form.1099-DA (Digital Asset Reporting)If you are required to file Form 1099-DA, it must be submitted through IRIS only.FIRE does not accept this form.This typically applies only to certain brokerages and digital asset platforms.Important Reminder on Form 1042 (No “S”)Form 1042 is subject to the e-file mandate.It does not go through IRIS or FIRE.Instead, it must be e-filed through the IRS MF (Mainframe) system.Not all filing vendors support MF, so filers should confirm capabilities now.No IRS paper-filing exception has been issued yet for 2025 (as of recording), though the form is not due until March 15.Publication 1099 (2026 Version) Signals FIRE’s FutureThe IRS reiterates its plan to shut down the FIRE system by the end of 2026.FIRE is mentioned only three times in the publication—all in the context of its shutdown.IRIS is referenced 26 times, underscoring the IRS’s clear long-term direction.Bottom line:This is a relatively quiet “What’s New” period—which is good news. Filers can focus on getting forms submitted while keeping an eye on:Form 1042 e-filing logistics, andThe ongoing transition away from FIRE toward IRIS.🎧 Tune in next week for the next episode of Information Return Intelligence.

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 significant implications for vendor setup and 1099 compliance.While the IRS has not yet finalized the form, the proposed change is more consequential than it may appear at first glance—particularly for individuals and sole proprietors.🔍 The Key Proposed ChangeUnder the draft Form W-9, vendors classified as individuals or sole proprietors would be required to provide a Social Security number (SSN) rather than an Employer Identification Number (EIN).Jason and Deborah explain:Why this change likely targets single-member LLCs taxed as sole proprietorsHow it could affect existing W-9s already on fileWhy this may create real-world friction for AP departments—even if the rule itself is technically simple🧠 What AP Departments Should Be Doing NowEven though the form is still in draft status, this episode outlines practical steps AP teams should consider:Don’t panic—the IRS has not finalized or announced an effective dateBookmark the official IRS W-9 PDF, not just the webpage, to catch silent updatesContinue focusing on timely 1099 and 1042 reporting obligationsEnsure TIN matching and vendor master data accuracy are already solid🔁 Re-soliciting W-9s: Will You Have To?One of the most important discussions in the episode centers on whether AP teams may need to re-solicit W-9s from existing vendors who:Are individuals or sole proprietors, andPreviously provided an EINDeborah and Jason discuss:How system limitations may make identification difficultWhy this change could be different from prior W-9 revisionsThe importance of consulting internal leadership and tax advisors before launching large-scale re-solicitation projects🔐 Data Security ConsiderationsBecause this change may increase the collection of SSNs, the episode also dives into data security best practices, including:Why email is a high-risk method for collecting W-9sUsing secure email platforms, portals, or SharePoint-style solutionsReducing unnecessary internal exposure to sensitive vendor dataThe value of documented procedures for vendor setup and maintenance🧾 A Case for Substitute W-9sDeborah also explains why substitute W-9 / vendor setup forms can be especially valuable when IRS forms change—and what compliance requirements companies must meet when using them.🎧 Final TakeawayThis episode reinforces a familiar reality in information reporting:The IRS doesn’t always give clear guidance—and sometimes you have to make reasonable, well-documented decisions in the absence of it.For AP professionals, preparation, process, and documentation remain the best defense.Guest: Deborah RichardsonAccounts Payable Consultant, Speaker & TrainerHost of Putting the AP in HappyHost: Jason DinesenInformation Return Intelligence

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 teams.We walk chronologically through the year, highlighting regulatory changes, IRS guidance, legislation, and draft forms that will shape reporting obligations in 2025 and beyond.Key topics covered include:January regulations on digital and cloud transactions Final regulations clarified how digital transactions are classified (royalty, sale, lease, services, or know-how), while new rules on cloud computing—such as SaaS—generally treat these arrangements as services, with major implications for 1099-NEC and 1042 reporting.Sourcing challenges for cloud transactions Proposed sourcing rules introduced a three-factor formula for U.S. vs. foreign sourcing—an approach widely criticized as impractical for information return filers.IRS ruling on tribal payments A private letter ruling confirmed that Native American tribes are subject to Section 6041 reporting, including issuing Forms 1099 for prize winnings such as powwow contest awards.The FIRE system sunset timeline The IRS stated—in writing—that the FIRE system is expected to shut down in December 2026, leaving IRIS as the sole electronic filing platform.The “Big Beautiful Bill” and information reporting Major highlights include:The long-awaited increase of the $600 reporting threshold to $2,000, effective in 2026 and indexed for inflation thereafterRollback of prior changes to Form 1099-K thresholdsNew deductions for tips and overtime, with downstream reporting implicationsSports gambling and Form 1042-S IRS guidance confirmed that sports gambling winnings paid to nonresident aliens are subject to Form 1042-S reporting and 30% withholding, absent treaty relief.Draft Form W-9 changes Draft versions released in September and December propose eliminating the ability for sole proprietors to provide an EIN instead of an SSN—a change still pending as of year-end.New reporting boxes for tips and overtime Draft 2026 versions of Forms 1099-NEC, 1099-MISC, and 1099-K include new boxes for tips and overtime, reflecting coordination challenges between IRS tax rules and Department of Labor standards.This episode ties together the biggest themes of 2025 and sets the stage for what filers need to watch heading into 2026—particularly threshold changes, IRIS adoption, and evolving worker classification issues.🎧 Listen now to get fully caught up before the new reporting year begins.

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. https://www.youtube.com/@InformationReturnIntelligenceCredits: A 1099 Christmas CarolWritten by: Jason DinesenAnimated by: Jason Dinesen in Runway (www.runwayml.com)Music: Joy to the World (Instrumental) by Matthew L. Fisher – license purchased by Dinesen Media Ventures, LLC through Audiio (www.audiio.com)Images for Animation: created in ChatGPT by Jason DinesenVoices:·       Roger Jackson: Jackson Dinesen·       Mr. Wiley, Ward Hussey, Roger’s father, IRIS: Jason Dinesen·       W-9: Tyler Dinesen·       2K: Tracy Dinesen

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 threshold under the Taxpayer First Act 🔹 How W-2s fit into the e-file mandate (and why it’s not an “IRS rule”) 🔹 The scheduled shutdown of the FIRE system in December 2026 🔹 What that shutdown really means for the 2025 filing season 🔹 When and how to transition to IRIS 🔹 Limitations inside IRIS — including the 100-form upload cap 🔹 New ability to file Form 1042-S on IRIS 🔹 The ongoing Form 1042 problem (Modernized e-File) and how to handle it 🔹 Whether it makes sense to file through IRIS yourself or use a vendor 🔹 Why many filers partner with third-party providers like AvalaraIf you deal with 1099s, 1042-S, W-9s, or electronic filing, this episode gives you the latest developments and practical steps to prepare for the coming changes.🎙 Hosted by Jason Dinesen — “The 1099 Guy” Fast, clear, practical intelligence for AP, payroll, and information-reporting pros.

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!)What You’ll LearnWhy the state boxes on a 1099 don’t fulfill your state filing obligationsHow to determine which states you need to file inWhy contractor location (and where the work is performed) mattersHow state backup withholding rules differ — especially California’sWhy some states only require 1099s if you did state-level backup withholdingHow federal threshold changes (like the move to $2,000) may not match state rulesTips for keeping up with changing state portals, thresholds, and requirementsA surprising trivia fact about two income-tax states with no 1099-NEC or 1099-MISC filing requirementsReferenced ResourcesIRS Publication 1220 (Combined Federal/State Filing Program chart)About This PodcastInformation Return Intelligence is your weekly briefing on the constantly shifting world of information return compliance — from 1099-NEC to 1042-S and beyond. Short, fast-moving, and packed with practical insights.

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 FLSA overtime could ever appear on a 1099… Jason discovered there is a rare situation where it actually can.Join Jason as he breaks down:What counts as “qualifying overtime” under the OBBBWhy Section 7 of the FLSA is the key to the deductionWhy most overtime won’t qualifyWhy overtime is almost always reported on a W-2And how — in extremely unusual cases — it might legitimately show up on a 1099Using IRS Notice 2025-69, Jason explains how a worker can be an employee under the Fair Labor Standards Act (DOL’s economic-realities test) while still being treated as a contractor for tax purposes (IRS three-factor test).It’s rare. Think unicorn rare. But it’s not impossible — and if it happens, employers need to know exactly why.If you deal with 1099s, W-2s, worker classification, or compliance in general, this episode is a must-listen.

The IRS has issued new guidance on reporting tips and overtime, and while these topics usually live in the W-2 world, they now have implications for 1099 filers as well.In this episode, Jason Dinesen — The 1099 Guy — explains how the Big Beautiful Bill created a new personal tax deduction for qualifying tips and qualifying overtime, and how upcoming changes to Form 1099-NEC and 1099-MISC will reflect this. Jason also breaks down the difference between voluntary and non-voluntary tips, why most overtime won’t qualify for contractors, and what AP and payroll teams need to track — even though processing the payments themselves won’t change.You’ll learn:The new tip & overtime deduction created by recent legislationWhat counts as a qualifying tip (and what doesn’t)Why qualifying overtime rarely applies to contractorsHow upcoming 2026 1099 forms will include new boxesWhat issuers must track for future reportingInformation Return Intelligence delivers weekly insights to help accounting and finance pros stay compliant with 1099, 1042-S, W-9, and related reporting rules.🎙️ Hosted by Jason Dinesen, EA — The 1099 Guy

The IRS quietly released a draft Form W-9 in mid-September — and one proposed change could have a major impact on how businesses collect taxpayer identification numbers from sole proprietors and single-member LLCs.In this episode, Jason Dinesen — The 1099 Guy — breaks down what’s in the draft, why the change matters, and what AP, procurement, and vendor onboarding teams should do now (and not do yet). This is a big one: the IRS is proposing that sole proprietors would no longer be allowed to provide an EIN — only a Social Security Number. Jason explains why this shift is happening, how LLC confusion plays into it, and what you’ll need to update if the draft becomes final.In this episode: 00:00 — Welcome to Information Return Intelligence 00:30 — Draft W-9 released in mid-September 01:40 — New digital asset broker checkbox 02:05 — The major proposed change: SSNs only for sole proprietors 03:00 — Why LLC confusion is driving this 04:20 — Current rules vs. proposed rules 06:25 — Why draft status matters (don’t change anything yet!) 07:40 — How to monitor the IRS W-9 page 09:10 — Will you need to re-solicit W-9s? Jason explains 11:00 — What to do now (and what not to do)🎙️ Hosted by Jason Dinesen — The 1099 Guy#1099 #W9 #TaxCompliance #VendorManagement #Accounting #InformationReturnsInformation Return Intelligence delivers weekly, practical insights on 1099s, 1042-S, W-9s, and the full ecosystem of information reporting — helping professionals stay compliant and a step ahead.🎙️ Hosted by Jason Dinesen, EA — The 1099 Guy

The $600 reporting threshold for 1099s has been with us since 1954 — older than Elvis and untouched by inflation. But starting with 2026 payments, it’s finally changing to $2,000 and will be indexed going forward.In this episode, host Jason Dinesen — The 1099 Guy — explains why the threshold lasted so long, what’s changing under the Big Beautiful Bill, and what steps accounting and finance professionals should take to prepare.You’ll learn:The history and legal background of the $600 ruleHow and when the new $2,000 threshold appliesWhat forms and transactions are affectedHow to prepare your systems for annual updatesInformation Return Intelligence delivers practical insights for accounting and compliance professionals who work with 1099s, 1042-S, and other information returns — helping you stay compliant, confident, and a step ahead.