Information Return Intelligence

Jason Dinesen

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

  1. 5 天前

    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. 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 regulations The often-overlooked consent requirements Why 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

    9 分鐘

  2. 4月14日

    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 formatting in IRIS? --Does the credit card exception apply to Form 1042-S? --What if a vendor checks box 3b on the W-9?

    12 分鐘

  3. 4月8日

    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 becomes clearer --2026 drafts of 1099-NEC and 1099-MISC --Treasury Department seeks comment on providing forms to recipients electronically --And more!

    14 分鐘

  4. 3月31日

    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 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.

    10 分鐘

  5. 3月24日

    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.

    11 分鐘

  6. 3月17日

    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.

    8 分鐘

  7. 3月10日

    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.

    14 分鐘

  8. 3月3日

    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 分鐘
顯示全部 (24)

簡介

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

資訊

  • 創作者
    Jason Dinesen
  • 活躍年代
    2025年 - 2026年
  • 集數
    24
  • 年齡分級
    兒少適宜
  • 版權
    © 2026 Information Return Intelligence
  • 節目網站
    Information Return Intelligence