Information Return Intelligence

Jason
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Your weekly briefing on 1099s, 1042-S, and everything related to information forms.

  1. 8H AGO

    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 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.

    14 min

  2. FEB 24

    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 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.

    12 min

  3. FEB 19

    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 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

    9 min

  4. FEB 10

    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 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 compliance How new Treasury regulations treat cloud transactions (including SaaS) What to review in your 1099 e-filing process, including FIRE vs. IRIS Common pain points with state 1099 filings and how to manage them Why written procedures matter—for efficiency and penalty protection This episode is ideal for: AP professionals Tax professionals Payroll and compliance teams Anyone responsible for issuing Forms 1099 or 1042-S Whether 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.

    7 min

  5. FEB 3

    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 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.

    8 min

  6. JAN 27

    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, 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.

    7 min

  7. JAN 20

    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 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.

    5 min

  8. JAN 13

    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 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.

    6 min
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Your weekly briefing on 1099s, 1042-S, and everything related to information forms.

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