Information Return Intelligence

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

Episodes

  1. 5D AGO

    Episode 9: Proposed Changes to Form W-9: What AP Teams Need to Know Now

    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 Change Under 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 proprietors How it could affect existing W-9s already on file Why this may create real-world friction for AP departments—even if the rule itself is technically simple 🧠 What AP Departments Should Be Doing Now Even 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 date Bookmark the official IRS W-9 PDF, not just the webpage, to catch silent updates Continue focusing on timely 1099 and 1042 reporting obligations Ensure 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, and Previously provided an EIN Deborah and Jason discuss: How system limitations may make identification difficult Why this change could be different from prior W-9 revisions The importance of consulting internal leadership and tax advisors before launching large-scale re-solicitation projects 🔐 Data Security Considerations Because 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-9s Using secure email platforms, portals, or SharePoint-style solutions Reducing unnecessary internal exposure to sensitive vendor data The value of documented procedures for vendor setup and maintenance 🧾 A Case for Substitute W-9s Deborah 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 Takeaway This 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 Richardson Accounts Payable Consultant, Speaker & Trainer Host of Putting the AP in Happy Host: Jason Dinesen Information Return Intelligence

    31 min

  2. 12/30/2025

    Episode 8: 1099 and 1042-S Year-in-Review

    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.

    15 min

  3. 12/23/2025

    Episode 7: A 1099 Christmas Carol

    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/@InformationReturnIntelligence Credits:  A 1099 Christmas Carol Written by: Jason Dinesen Animated 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 Dinesen Voices: ·       Roger Jackson: Jackson Dinesen ·       Mr. Wiley, Ward Hussey, Roger’s father, IRIS: Jason Dinesen ·       W-9: Tyler Dinesen ·       2K: Tracy Dinesen

    8 min

  4. 12/16/2025

    Episode 6: E-Filing Updates

    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 Avalara If 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.

    13 min

  5. 12/09/2025

    State 1099 Filing Rules Explained

    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 Learn Why 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 Resources IRS Publication 1220 (Combined Federal/State Filing Program chart)About This Podcast Information 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.

    13 min

  6. 12/02/2025

    Overtime on a 1099? Rare But Possible

    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.

    9 min

  7. 11/25/2025

    Tips & Overtime on 1099s: What You Need to Know for 2025–2026

    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

    9 min

  8. 11/18/2025

    The W-9 Shake-Up: What the New Draft Form Could Mean for Sole Proprietors

    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 #InformationReturns Information 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

    12 min

  9. 11/12/2025

    The $600 Threshold’s Long Goodbye

    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.

    11 min
  • 9 Episodes

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

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