Information Return Intelligence

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

  1. قبل ٤ ساعات

    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.

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  2. ٣ فبراير

    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.

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  3. ٢٧ يناير

    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.

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  4. ٢٠ يناير

    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.

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  5. ١٣ يناير

    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.

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  6. ٦ يناير

    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

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  7. ٣٠‏/١٢‏/٢٠٢٥

    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.

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  8. ٢٣‏/١٢‏/٢٠٢٥

    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

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

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