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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

Two years ago, we packed up our lives in Iowa and moved to Portugal. We expected plenty of changes—but one of the biggest surprises was how much the move transformed our marriage and our family life. In this episode, we talk honestly about the burnout we experienced in the United States, how slowing down changed the way we communicate, and why having time and space for each other has made such a difference. We also discuss rediscovering hobbies, prioritizing mental and physical health, and why

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...

For years, we told ourselves—and everyone else—that our move to Portugal might only be temporary. First it was six months. Then maybe two years. But here we are, more than three years later, and we're still here. In this episode of As the Dinesens Turn, we reflect on why we chose to stay. It's not just about Portugal itself. It's about the unexpected ways our priorities changed, how our family life evolved, and why we discovered that the life we wanted looked very different from the one we had