Information Return Intelligence

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

  1. 3일 전

    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 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.

    11분

  2. 3월 17일

    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 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.

    8분

  3. 3월 10일

    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 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.

    14분

  4. 3월 3일

    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.

    14분

  5. 2월 24일

    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.

    12분

  6. 2월 19일

    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

    9분

  7. 2월 10일

    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.

    7분

  8. 2월 3일

    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.

    8분
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Your weekly briefing on 1099s, 1042-S, and everything related to information forms.

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    Jason
  • 방송 연도
    2025년 - 2026년
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    20
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