Procedural Pitfalls and Million-Dollar Mistakes: A Tax Case Roundup

Procedural Pitfalls and Million-Dollar Mistakes: A Tax Case Roundup

In this episode, Joel Crouch and Matt Roberts examine a series of recent tax cases and enforcement developments highlighting how procedural missteps, aggressive positions, and poor documentation can quickly escalate into substantial penalties and prolonged disputes with the IRS. The discussion explores several notable Tax Court and appellate decisions involving conservation easements, partnership reporting issues, substantiation failures, and penalty challenges, with a focus on how courts are evaluating taxpayer conduct and reasonable cause defenses in today's enforcement environment. Joel and Matt also analyze the practical implications of recent ruling affecting IRS procedure, litigation strategy, and taxpayer rights, including cases that demonstrate the significant consequences of missed deadlines, incomplete records, and flawed transactional planning. Throughout the episode, they offer practical guidance for taxpayers and practitioners navigating audits, appeals, and high-stakes tax controversy matters in an increasingly technical and penalty-driven landscape.

Tax Trouble Tales: Recent Cases, Big Penalties, and IRS Pitfalls

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.

Bad Facts, Big Penalties: Recent Tax Cases Redefining Penalties and Procedure

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.

No Profit, No Problem? Analyzing the Section 183 Hobby Loss and Section 469 Passive Activity Rules

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.

From Filing to Finality: Navigating the IRS Statute of Limitations

In this episode, Joel Crouch and Matthew Roberts explore all things IRS statutes of limitations - the timeframes that govern how long the IRS has to assess or collect taxes, and how long taxpayers have to file refund claims. They break down the general three-year rule and dive into the many exceptions that can extend or suspend the clock, including issues involving foreign reporting, bankruptcy, and fraud. From assessment and collection to refund claims and protective filings, Joel and Matt  discuss common traps, strategic considerations, and real-world examples that illustrates how timing can make or break a tax case. Whether you're managing an examination, filing an amended return, or weighing an IRS extension request, gain practical insights to help taxpayers and practitioners navigate the ticking clock with confidence.