Loopholes Archives - Think Outside the Tax Box
By Lewis C. Taishoff

TAX COURT ROUNDUP – February 2026

I can’t say that 2025 was anything less than tumultuous, or that 2026 isn't likely to be more of the same. Boechler, P. C., Jarkesy, Zuch, the Affordable Care Act, FBAR, and even long-gone FASIT and SDLIA are already starting the year. Come along for the ride!

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Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond

One of my greatest frustrations as a tax writer is that I just don’t have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the college professors I envied. Even that did not keep up with everything I noticed, so periodically I would do a post that had short blurbs about interesting things I didn’t dig further on. Here is an example from 2010 of a post that covers an entity not considered a church by the IRS, S corp shareholder basis issues, definition of alimony and two Chief Counsel Advices on TEFRA issues. So here are some things for 2025, that I opened a file on but never managed to make an article with.

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TAX COURT ROUNDUP – January 2026

Though 2025 was a gamechanger in many ways, Tax Court went on resolving controversies both arcane and mundane. Inventive counsel tried extending Supreme Court pronouncements and stretching narrow jurisdictional limits as always, Tax Court dealt with the Supreme Court's efforts to bring "discipline" to Tax Court practice, and self-represented petitioners continued to wander into sand traps of their own making.

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This Is The Only Other Year-End Tax Tip Guide You Need

So as I did last year, I have reviewed a multitude of year-end tax tips articles. One of them is a real standout that you should be sure to check out. If you missed it, you should definitely roll back to the November 15 edition and go over Dominique Molina’s piece, which focuses on what you need to do sooner rather than later in response to OBBBA. It provides more detailed, relevant, actionable advice that you won’t see anywhere else than any of the multitude of pieces I have reviewed. As for the rest, I will give you a basic rundown of what I call the SOSO (same old, same old) and a few suggestions that stand out as different that I will get into a little more along with some thoughts of my own.

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The Corporate Vault: How to Use a C Corporation to Stockpile Cash for the Future

When most people think about saving for the future, their minds jump to retirement accounts—401(k)s, IRAs, maybe even defined benefit plans. But business owners have another option that often goes overlooked: using a C corporation as a strategic savings vehicle. By leveraging the flat 21% corporate tax rate, smart income shifting, and careful timing of distributions, business owners can “stockpile” cash inside a corporation, building wealth for future use without the red tape of traditional retirement plans. Want to see how top tax strategists legally use C corporations as private retirement vaults while avoiding double taxation and IRS scrutiny? Continue reading to learn the blueprint.

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Client Alert

TAX COURT ROUNDUP – December 2025

An updated website launches, the economic substance codification is applied, Loper Bright Entrprs. marches on but hits the statute, and the syndicated conservation easement flood continues, as Tax Court pushes through the government shutdown. The biennial examination for non-attorney admission to Tax Court took place as scheduled.

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TAX COURT ROUNDUP – November 2025

Though the government was shut down all month, and trial sessions were canceled, Tax Court carried on. Online improvements were forecast, the equitable tolling saga continued, and self-represented novelties featured this month.

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Taxes & Taxidermy: Rampaging Through The Tax Code On The Back Of A Stuffed Rhinoceros

Is the taxidermy fee for a stuffed bear deductible? If so, should I depreciate it? What would the basis and class life be for depreciation? Those are real questions asked in a group chat with some colleagues. Of course my answer was “It depends.” And, like all good tax professionals, I proceeded to ask a series of follow-up questions. And, like a good writer, that got me to thinking about all of the tax-related case law surrounding taxidermy and what it can teach us—it’s more than one might think.

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TAX COURT ROUNDUP – October 2025

There are new insights and old unresolved questions in this month's instalment. There's always the old and new.

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