Guest Article

Dealing with deficiency and restitution in a tax evasion case is a minefield, but there's a good example of how it's done this month. There's architecture, both additional research credits for buildings and software in discovery. There are the fine points of the innocent spouse checklist, Rev. Proc. 2013-34. Two common deductions, home office and hobby losses, get reexamined. Cryptocurrency staking is taxed. A brilliant move earns a much-belated refund of an enhanced accuracy penalty. And the scoresheet in the Boechler jurisdiction-vs-claim-processing gets a new entry.

The Internal Revenue Service has made no secret of its increased scrutiny of captive insurance arrangements, particularly those involving the small insurance company election. For taxpayers and their advisors, this has created understandable concern and, in some cases, hesitation about whether captive insurance remains a viable risk management and tax planning tool. Yet heightened scrutiny does not mean prohibition. The Internal Revenue Code continues to recognize captive insurance, Congress has refined it, and courts evaluate it based on well-established insurance principles. The real issue is not whether captives are allowed, but whether a specific taxpayer has a legitimate business need for insurance, has structured the arrangement properly, and has implemented it in a manner consistent with both tax law and insurance fundamentals. Understanding where scrutiny arises, how elections function, and what separates compliant captives from problematic ones is critical for CPAs advising closely held businesses today.

Reilly’s Sixteenth Law of Tax Planning – Being right without substantiation can be as bad as being wrong – is particularly apt when it comes to charitable contributions. The case law makes it clear that there is not much wiggle room in rules relating to substantiation and reporting of charitable contributions. We’ll dig into the rules here.

At some point, accounting becomes more than compliance. It's years of watching businesses evolve, owners under pressure, and consequences unfold. We soon recognize the gap between what clients ask for and what they need. That quiet, steady understanding, grounded in experience, shapes the growth-minded accountant.

Tax Day is finally in the rearview mirror, and if you’re like many practitioners—with the phones quieter, the inbox manageable, and the September extension wave feeling comfortably far away—the temptation right now is to coast. Resist that temptation. Summer is the only stretch of the calendar when both you and your best clients have the bandwidth to think strategically; furthermore, this summer, there is a deadline-driven opportunity. In this article, I’ll walk through three moves every practitioner should be making between now and Labor Day. The first move has a hard statutory deadline of July 10, 2026. The second move is about turning your highest-value client conversations into billable advisory engagements. And third is about tending to the practice itself because a tax practice, like a garden, doesn’t survive without care.

Perhaps the most misunderstood aspect of partnership taxation relates to distributions. When a partnership distributes cash or property to its partners, the tax consequences can range from completely tax-free to significantly taxable, depending on how the distribution is structured and the partners' tax basis in their partnership interests. In this article, we'll explore the rules governing partnership distributions and how they impact partners' tax situations. More importantly, we'll look at strategies to structure distributions in the most tax-efficient manner possible – because the goal is not just to understand the rules but to use them advantageously.

The Jeffrey Winick tax story is about one of the simplest methods of not paying taxes. That simple method of not paying is simply not paying. Winick is a very successful real estate broker specializing in retail leases. The company he founded, Winick Realty (now rebranded RTL), has in the past been listed as one the top five of retail brokers in New York City. As far as my friend Grok can discern, Winick managed all this with no formal education beyond high school. That makes it extra impressive. I identify with him just a bit. He grew up in Kew Gardens Hill, Queens, New York, and is 75 years old. I also grew up not far from Manhattan and am 74. I sometimes fantasize about living in Manhattan. He's living there, and apparently he was really living. His lifestyle was a major topic in the litigation.

I'm almost nostalgic for the days of 2021-2022, the COVID-induced tsunami of Tax Court filings and cases. This month we've seen only eight T. C. Memos, of which two were routine undocumented deduction cases (Section 6001 or Section 274), no Sum. Ops, and no T. C.s. It's been years since practitioners murmured the old, nearly-forgotten slogan as they booked their summer vacations: "File in May and go away," but it may be time again. Here's what happened.