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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.

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 ex

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 withh

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 matters How COVID-era deadline suspensions factor

In this episode of Information Return Intelligence, Jason breaks down a recent IRS private letter ruling that answers a deceptively simple question: Do tax-exempt organizations still have 1099 reporting obligations? The ruling involved a Native American tribe that awarded prize money at a powwow and questioned whether those payments required Form 1099 reporting. The tribe made three key arguments: They are not subject to income tax They are not a “person” under the tax code The activity was not

At this year’s IOFM Spring Conference in Orlando, one theme kept surfacing over and over again: uncertainty. In this episode of Information Return Intelligence , Jason shares his biggest takeaways from conversations with AP professionals, compliance teams, and attendees across the conference floor. While the sessions themselves were valuable, the real insights came from listening to the concerns people are facing every day in the information reporting world. Three major themes emerged: • Growing