Episodes

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.

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.

Single-member LLCs and Form W-9 continue to cause confusion — especially when it comes to which taxpayer identification number (TIN) should be provided. In this episode of Information Return Intelligence, Jason Dinesen tackles a common (and frustrating) issue: single-member LLCs taxed as disregarded entities providing the LLC’s EIN instead of the owner’s Social Security number (or the owner’s EIN, if they have one personally). Accounts payable professionals often push back when vendors submit ...

You filed your 1099s. Now you found a mistake. What do you do? In this episode of Information Return Intelligence, I break down: ✅ Why we file 1099s in the first place (hint: it’s about IRS matching programs and tax compliance)✅ How the IRS actually uses the data you submit✅ What kinds of errors matter (and which ones don’t)✅ When you are required to file a correction✅ The key August 1 deadline that can help you avoid penalties✅ The de minimis dollar error rule ($100 / $25 for backup withhold...

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 igno...

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...

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 ...

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 Suppor...

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...