Information Return Intelligence

Jason Dinesen

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

  1. há 22 h

    Episode 35 -- Second Quarter Form 1099 Roundup

    Q2 2026 Roundup: W-9 Drafts, Backup Withholding, IRIS Updates & More The second quarter of 2026 brought a surprising number of developments in the information reporting world, and in this episode of Information Return Intelligence, Jason Dinesen breaks down the biggest stories that matter to 1099 professionals. Topics include the latest draft Form W-9 and the IRS's reversal on the proposed EIN restriction for sole proprietors, proposed regulations updating backup withholding thresholds, revisions to Forms 1099-NEC and 1099-MISC, and a quiet but important expansion of the IRIS Taxpayer Portal from 100 to 250 forms per upload. Jason also covers Treasury's proposed changes to electronic delivery rules, the potential implications of the Kwong case for certain tax penalties, and reflects on key themes that emerged from conversations with practitioners at the IOFM Spring Conference in Orlando. Whether you issue information returns, advise clients, or simply want to stay current on IRS developments, this quarterly roundup provides a practical overview of the most important news from April through June. In this episode: Draft Form W-9 updates and what changed (prior episode: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/latest-w-9-draft-irs-reverses-course-on-sole-proprietor-ein-rule/) Backup withholding proposed regulations (prior episode: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/treasury-aligns-backup-withholding-with-new-1099-reporting-thresholds/) New reporting boxes on Forms 1099-NEC and 1099-MISC (prior episode: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/irs-releases-2026-version-of-1099-nec-and-1099-misc/) IRIS Taxpayer Portal expands to 250-form uploads Treasury's proposed electronic delivery regulations (two prior episodes: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/treasury-department-seeks-public-input-on-easing-e-delivery-rules/ and https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/e-delivery-rules-for-1099s-why-emailing-pdfs-isnt-so-simple/) The Kwong decision and why July 10 matters (prior episode: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/the-kwong-case-a-big-tax-deal-but-what-about-information-returns/) Takeaways from the IOFM Spring Conference (prior episode: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/iofm-conference-takeaways-anxiety-complexity-and-ai/) Subscribe for weekly updates covering Forms 1099, 1042-S, W-9, backup withholding, IRS guidance, and other information reporting developments.

    20 min

  2. 30 de jun.

    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 reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The history of Form 1099-K The American Rescue Plan Common misconceptions about Venmo reporting IRS enforcement challenges Why more information reporting isn't always better ▶️ Subscribe for weekly updates on Forms 1099, 1042-S, W-9, backup withholding, and other information reporting topics. Learn more: 🌐 https://podcasts.dinesenmedia.com Powered by IOFM -- www.iofm.com

    18 min

  3. 30 de jun.

    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 reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The history of Form 1099-K The American Rescue Plan Common misconceptions about Venmo reporting IRS enforcement challenges Why more information reporting isn't always better ▶️ Subscribe for weekly updates on Forms 1099, 1042-S, W-9, backup withholding, and other information reporting topics. Learn more: 🌐 https://podcasts.dinesenmedia.com Powered by IOFM -- www.iofm.com

    18 min

  4. 30 de jun.

    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. Find Part 1 here. Why did Congress originally push for the change? What was it hoping to accomplish? And why did lawmakers ultimately reverse course and restore the original $20,000 and 200-transaction threshold? In this episode, Jason explores the policy goals behind the proposal, addresses several common misconceptions—including the myth that the IRS was "coming for everyone's Venmo transactions"—and discusses two major practical problems that ultimately undermined the lower threshold:  Whether reporting thousands of very small businesses would meaningfully increase tax revenue.  Whether the IRS could realistically process and enforce compliance on an estimated 33 million Forms 1099-K each year. Using real-world examples, this episode looks at the balance between increased reporting, taxpayer compliance, and the realities of tax administration. This is Part 2 of our ongoing Form 1099-K series. Part 1 covers the fundamentals of the form, while Part 3 will bring the discussion back to what accounts payable departments, businesses, and information return filers need to know today. In this episode  The history of the Form 1099-K reporting thresholds  Why Congress proposed a $600 threshold  The American Rescue Plan and subsequent legislative changes  Common misconceptions about Venmo and personal payments  Two major criticisms of the lower threshold  IRS workload projections and enforcement challenges  Why more reporting does not always mean better enforcement Information Return Intelligence is powered by the Institute of Finance & Management (IOFM). ▶️ Subscribe for weekly updates on Forms 1099, 1042-S, W-9, backup withholding, and other information reporting topics. Learn more:  🌐 https://podcasts.dinesenmedia.com #1099 #1099K #Tax #IRS #AccountsPayable #InformationReporting #IOFM #GigEconomy

    18 min

  5. 23 de jun.

    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, particularly regarding worker classification and the reporting of tips for contractors.

    12 min

  6. 15 de jun.

    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'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.

    12 min

  7. 9 de jun.

    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 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.

    8 min

  8. 2 de jun.

    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 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

    11 min
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Sobre

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

Informações

  • Criado por
    Jason Dinesen
  • Anos de atividade
    2025 - 2026
  • Episódios
    37
  • Classificação
    Livre
  • Copyright
    © 2026 Dinesen Media Ventures, LLC
  • Site do podcast
    Information Return Intelligence

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