In this episode, Joel Crouch and Matt Roberts walk through a wide-ranging update on recent tax cases and developments shaping the current tax controversy landscape. They begin with the Fifth Circuit's closely watched decision in Sirius Solutions LLLP v. Commissioner, examining the court's rejection of the Tax Court's functional analysis for limited partners and what the ruling means for self-employment tax exposure and audit strategy. They then turn to a series of cautionary tales from the Tax Court and federal courts, including an estate tax case illustrating the risks of late filings and executor liability. The discussion also covers evolving developments in FBAR willfulness following the Second Circuit's Reyes decision, as well as ongoing Seventh Amendment challenges to civil tax penalties. Joel and Matt offer practical takeaways for taxpayers and practitioners alike, highlighting how bad facts, procedural shortcuts, and shifting precedent can dramatically affect penalty exposure, litigation risk, and audit outcomes.

In this episode, Joel Crouch and Matt Roberts take a deep dive into several recent tax cases shaping today's tax controversy landscape. They begin with Patel, a precedential Tax Court decision addressing captive insurance transactions and the application of accuracy-related penalties for lack of economic substance, including what constitutes adequate disclosure and why the absence of a reasonable cause defense can be so consequential. Joel and Matt then turn to a series of jurisdictional cases following Boechler, examining whether statutory filing deadlines in Tax Court are truly jurisdictional or subject to equitable tolling and what recent circuit court decisions mean for taxpayers who miss those deadlines. The discussion also covers partnership audit timing issues under the former TEFRA regime, as well as emerging Seventh Amendment challenges to civil tax penalties in the wake of recent Supreme Court precedent. This episode offers practical insights into audit strategy, penalty defense, and procedural pitfalls.

In this episode, Mary Wood and Josh Ungerman break down two often-confused provisions in the Internal Revenue Code: Section 183, the hobby loss rules, and Section 469, the passive activity loss rules. They explain how the IRS determines whether an activity is a genuine business or a personal pastime, and why the distinction can mean the difference between deductible losses and permanent disallowance. From the nine factor profit motive test to the material participation standards, Mary and Josh discuss how taxpayers can document intent, track time, and substantiate their activities to withstand IRS scrutiny. They also share practical strategies for grouping activities, maintaining contemporaneous records, and addressing common audit pitfalls. This episode offers real-world guidance for defending profit motive and preserving valuable deductions.