Information Return Intelligence

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,...

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 settl...

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...

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 ...

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 e...