Information Return Intelligence

In this week’s Information Return Intelligence, it’s time for another round of Ask the Experts. I dig into four real-world questions that show how quickly information reporting can go from “this should be easy” to “well, actually…” We cover: B Notices: Publication 1281 says the outer mailing envelope must be marked “Important Tax Information Enclosed” or “Important Tax Return Document Enclosed.” Does having those words visible through a window envelope count?Wage garnishments: Are payments se...

The IRS recently released new FAQs dealing with the deduction for qualified overtime compensation. At first glance, this would seem to have nothing to do with 1099s. Overtime is generally an employee issue, which means W-2 reporting. But buried in the FAQs is an interesting question: When would qualified overtime compensation be reported on Form 1099-MISC or 1099-NEC instead of Form W-2? Yes, that can happen. The issue comes down to worker classification. The Department of Labor and the...

If your organization pays a legal settlement, and part of that settlement goes directly to the plaintiff's attorney, should that attorney portion be included on the plaintiff's Form 1099-MISC? The answer is yes. In this week's episode of Information Return Intelligence, Jason reviews the recent Eiler v. Commissioner decision, which reinforces a long-standing principle of tax law: the plaintiff is generally taxed on the entire taxable settlement, including amounts paid directly to their attorne

Every year, there's a little-known deadline that can save 1099 filers from costly IRS penalties. In this episode of Information Return Intelligence, Jason explains why August 3, 2026 (normally August 1) is such an important date for correcting information returns. Learn how the IRS treats errors on timely filed forms, how many corrections you can make without penalty, and which mistakes don't require correction at all. Jason also discusses the de minimis error rules, why intention...

Have a tricky 1099 question? You're not alone. In this fourth installment of our Ask the Expert series, Jason Dinesen answers real-world questions submitted by accounts payable and tax professionals. These are the kinds of scenarios that don't always have obvious answers—but they're exactly the situations finance teams encounter every day. This episode covers: When credit card payments shift reporting from Form 1099 to Form 1099-K—and why the same rule doesn't apply to Form 1042-SWhethe...

The IRS has introduced a new feature that allows businesses to instantly download verification of their Employer Identification Number (EIN) through their online Business Tax Account. It's a welcome improvement—but does it satisfy the documentation requirements for a second B Notice after receiving a CP2100? In this episode of Information Return Intelligence, Jason Dinesen examines the new online EIN verification process, explains how the CP2100 and B Notice procedures work, and answers the pra