Information Return Intelligence

Jason Dinesen

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

  1. 5d ago

    Episode 51: IOFM Fall Conference in One Week

    This week, we talk to Jess Scheer with our sponsor, IOFM, about the upcoming IOFM Fall Conference in Austin, Texas.  Jess and I have a conversation about the conference and the challenges facing today's AP professionals. One of the topics in Austin will be the growing role of artificial intelligence in accounts payable, the importance of networking and benchmarking, and how AP departments can become more strategic within their organizations. We also explore IOFM's certification programs, its new online community, IOFM Circle, and the value of getting expert answers to complex Form 1099 questions. Learn more about IOFM at https://www.iofm.com.

  2. Oct 20

    Episode 50: What Are Medical Damages?

    A court case earlier this year gave us two 1099 lessons. It wasn't a 1099 case, but we can take these lessons from it: 1. What are medical damages? 2. Whose settlement is it? In this episode, we discuss how the law says most lawsuit settlements are taxable, and thus reportable on a 1099. One of the exceptions is with medical damages. The best assumption to make is, the settlement is not for medical damages unless the settlement agreement explicitly says so.  On the subject of whose settlement is it -- the court case at issue involved two people who were party to a lawsuit. A settlement was paid to one of these people, and that person got the 1099 ... but the IRS said both people owned the income and should have reported the settlement 50/50. This subject can get trickier for an issuer of a 1099. Find all of our episodes at podcasts.dinesenmedia.com

  3. Oct 14

    Episode 49: USPS Postmark Changes: What 1099 Filers Need to Know

    A recent change in U.S. Postal Service postmarking procedures could create unexpected problems for anyone mailing time-sensitive documents to the IRS. In this episode of Information Return Intelligence, we explain why dropping your Forms 1099 in the mail before the final pickup time may no longer guarantee a same-day postmark — and why that matters for meeting IRS filing deadlines. You'll learn: What changed in the USPS postmarking process and why postmarks may be delayed.How the change could affect the timely filing of paper Forms 1099 and other tax documents.How to protect yourself by requesting a postmark at the post office counter and using certified mail.Why electronic filing avoids these mailing concerns, and how filing deadlines apply to electronic submissions.Whether you still file Forms 1099 on paper or have transitioned to electronic filing, this episode offers practical guidance for avoiding preventable late-filing problems. Information Return Intelligence is powered by IOFM and produced by Dinesen Media Ventures.

  4. Oct 6

    Episode 48: 3rd Quarter 2026 Roundup

    The third quarter of 2026 brought plenty of developments in the world of information reporting. In this episode, Jason breaks down what 1099 professionals need to know from July, August and September. You’ll learn about the upcoming shutdown of the FIRE system and transition to IRIS, what to watch for during CP2100 and B Notice season, the status of the long-awaited Form W-9 update, changes to Forms 1099-NEC and 1099-MISC, new information returns, updated 1099-K backup withholding rules, and other IRS and Treasury developments that could affect information reporting and compliance. For more detail on each development, check out this blog post: https://propelcareerlab.com/information-return-news-roundup-third-quarter-2026 Links to companion podcasts on these subjects: IRIS to FIRE: https://podcasts.dinesenmedia.com/show/information-return-intelligence/fire-extinguished/ CP2100 Letters: https://podcasts.dinesenmedia.com/show/information-return-intelligence/its-cp2100-letter-season/ Letter 147C: https://podcasts.dinesenmedia.com/show/information-return-intelligence/new-online-ein-verification-and-second-b-notices-can-you-use-it/ Substitute forms: https://podcasts.dinesenmedia.com/show/information-return-intelligence/substitute-forms-a-bigger-1099-deal-than-youd-think/ 1099-NEC and 1099-MISC 2026 versions: https://podcasts.dinesenmedia.com/show/information-return-intelligence/irs-releases-2026-version-of-1099-nec-and-1099-misc/ IRS FAQs on overtime and tips: https://podcasts.dinesenmedia.com/show/information-return-intelligence/irs-releases-faqs-on-overtime-with-one-1099-item/ Tax Court case on legal settlements: https://podcasts.dinesenmedia.com/show/information-return-intelligence/settlement-payments-attorney-fees-and-1099-reporting/

  5. Sep 29

    Episode 47: Does the B Notice Wording Really Have to Be on the Envelope?

    It’s “B” Notice season — and this week, we’re getting very specific about envelopes. When a payer receives a CP2100 notice from the IRS, one of the potential next steps is sending a “B” Notice to the payee. And the IRS has some very particular requirements for how that notice must be sent. Publication 1281 says the outer mailing envelope must include the words “Important Tax Return Document Enclosed” or “Important Tax Return Information Enclosed.” But what exactly does “on the outer mailing envelope” mean? A recent Ask the Expert question raised an interesting alternative: Could the required wording simply be printed on a document inside a window envelope, positioned so that the words are clearly visible through the window? It sounds like an incredibly minor detail. But for an organization sending large numbers of “B” Notices, changing the mailing process or purchasing specially printed envelopes can have real operational and cost implications. In this episode of Information Return Intelligence, Jason Dinesen looks at what Publication 1281 actually requires, how the regulations point payers back to IRS-established procedures, and why the safest reading is also the most literal one: put the required wording on the outer mailing envelope itself. We also cover an important reminder that can easily get overlooked in an increasingly electronic world: under the current procedures, “B” Notices still have to be sent by mail. It’s a short episode about a very narrow question — but sometimes those tiny procedural details are exactly where information reporting gets interesting. Information Return Intelligence is sponsored by the Institute of Finance & Management (IOFM) and produced by Dinesen Media Ventures.

  6. Sep 22

    Episode 46: It’s CP2100 Letter Season!

    Just like football season, CP2100 letter season has arrived. A CP2100 letter means the IRS found a problem when trying to match a name and taxpayer identification number (TIN) reported on a 1099 with the information in its records. So what should you do when one shows up? In this episode of Information Return Intelligence, Jason Dinesen walks through the CP2100 process from start to finish, including: Why the IRS sends CP2100 lettersWhy you should review your own records before contacting the payeeWhen a mismatch requires a B NoticeHow to determine the all-important “basis date”The 15- and 30-business-day deadlinesThe difference between a first and second B NoticeWhat documentation is required from the payeeWhen backup withholding may become necessaryWhy you generally don’t need to file corrected 1099s or report your response back to the IRSCP2100 letters can look intimidating, but there is a process for dealing with them. The key is understanding what the IRS is telling you, determining whether action is actually required, and then following the B Notice procedures and deadlines when necessary. Information Return Intelligence is sponsored by IOFM and produced by Dinesen Media Ventures.

  7. Sep 15

    Episode 45: Want to Use IRIS? Start the Process Now

    FIRE is going away. If you haven't figured out what you're doing next, now is the time. In the latest episode of Information Return Intelligence, Jason Dinesen looks ahead to the end of the FIRE system and explains why businesses shouldn't wait until January to make the move to IRIS—or to find a third-party filing provider. For organizations planning to file directly through IRIS, getting started involves more than simply creating an account. You'll need to determine whether you're using the Taxpayer Portal or the Application-to-Application (A2A) system, apply for the appropriate Transmitter Control Code (TCC), and potentially complete testing before you're ready to file. And don't assume your old FIRE credentials will carry over: a FIRE TCC won't work with IRIS. Planning to use a vendor instead? There's still work to do. Vendor onboarding, system setup, data preparation, and the inevitable learning curve all take time—especially for organizations filing larger volumes of information returns. The filing season may still seem months away, but that's exactly why now is the time to get started. In this episode: Why the November shutdown of FIRE matters nowThe Taxpayer Portal vs. A2A options within IRISWhy FIRE TCCs don't transfer to IRISThe potential 45-day wait for a new TCCA2A testing requirementsThe 250-record CSV limit in the Taxpayer PortalWhy vendor onboarding shouldn't wait until JanuaryThe case for outsourcing your information-return filingWhether you're planning to handle IRIS yourself or rely on a vendor, the message is simple: don't make this a January project. Information Return Intelligence is powered by IOFM and produced by Dinesen Media Ventures.

  8. Sep 8

    Episode 44: Form 1099-K Part 3

    This week on Information Return Intelligence, we wrap up our three-part series on Form 1099-K by tackling a common question: Why not just issue a Form 1099-NEC and avoid all the complexity? The answer is simple: because the regulations say not to. Here are the other parts:  Part 1 Part 2 When 1099-K Takes Priority Suppose you pay a contractor $1,000 by check or ACH in April and another $1,000 through a payment app in July. If the July payment is made in a way that transfers the reporting obligation to the payment app, you are responsible only for the $1,000 April payment for purposes of Form 1099-NEC. That creates an interesting result. You paid the contractor $2,000 during the year, and your books may show $2,000 of contract labor expense. But because only $1,000 is subject to reporting by you, you would not issue a Form 1099-NEC under the $2,000 reporting threshold applicable for 2026. This is why businesses need systems capable of distinguishing between payments potentially reportable on Form 1099-NEC and payments potentially reportable on Form 1099-K. Why Not Report Everything Yourself? A common response is: Why bother sorting through all of this? Why not simply report the entire $2,000 on Form 1099-NEC? The regulations under Sections 6041 and 6041A provide that transactions subject to both those reporting provisions and the Form 1099-K rules of Section 6050W are reported under Section 6050W — not under the Form 1099-MISC or 1099-NEC rules. This is different from the familiar corporate exception. Generally, you aren't required to issue a Form 1099 to a corporation, although there are exceptions such as certain legal and medical payments. But the corporate exception generally does not prohibit you from voluntarily issuing a Form 1099. The Form 1099-K rules are different. If a transaction could be subject to Form 1099-K reporting, the regulations direct the transaction into the Section 6050W reporting regime rather than the Form 1099-MISC or 1099-NEC regime. What If No 1099-K Is Actually Issued? That doesn't necessarily change your responsibility. Certain third-party settlement organizations may not actually issue a Form 1099-K because the payee doesn't meet the applicable transaction and dollar thresholds. But the regulations tell the payer to disregard those thresholds when determining whether the payment should instead be reported on Form 1099-NEC or Form 1099-MISC. In other words, the fact that the contractor ultimately doesn't receive a Form 1099-K doesn't automatically mean you should issue a Form 1099-NEC instead. The Practical Takeaway Businesses can't solve the complexity of Form 1099-K by simply saying, "We'll issue a 1099-NEC for everything." Instead, you need to know how each payment was made and who has the reporting obligation. That becomes especially important when the same contractor is paid in multiple ways during the year — perhaps by ACH, credit card, PayPal, Venmo, or another payment method. The amount you ultimately report on Form 1099-NEC could be very different from the contractor's total payments for the year. One way to make this easier is to consolidate payment methods whenever possible. The fewer ways you pay contractors, the easier it becomes to track transactions and determine who is responsible for information reporting. Listen to the full episode of Information Return Intelligence for the details and examples.

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About

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

Information

  • Creator
    Jason Dinesen
  • Years Active
    2025 - 2026
  • Episodes
    53
  • Rating
    Explicit
  • Copyright
    © 2026 Dinesen Media Ventures, LLC
  • Show Website
    Information Return Intelligence