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Do You Know U.S. Tax History?

In recognition of the 250th anniversary of the adoption of the Declaration of Independence on July 4, 1776, let’s review 250 years of tax history. Our nation’s tax systems have evolved over two and a half centuries as ways of doing business and living have changed. Also, expectations of services the public wants and needs from the government have grown, resulting in tax changes to generate increasing amounts of tax revenue. Along the way, lawmakers have considered principles of simplification, equity, fairness, economic growth and effective tax administration that have shaped our tax laws. This article offers questions and answers to cover a range of interesting aspects of our federal tax history.

Do You Know U.S. Tax History? Read More »

No Goods Or Services? Say It Explicitly: Tax Court’s Message In Martin v. Commissioner

Two recent Tax Court opinions , both about the same transaction, reinforce the importance of a contemporaneous written acknowledgement (CWA) to solidify charitable contributions. It is a good illustration of Reilly’s Fourth Law of Tax Planning – Execution isn’t everything, but it’s a lot.

No Goods Or Services? Say It Explicitly: Tax Court’s Message In Martin v. Commissioner Read More »

TAX COURT ROUNDUP – July 2026

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.

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What Happens If You Can’t Use All Your Clean Energy Tax Credits This Year?

Clean energy tax credits have a lot going for them. Clients buy them at a discount, apply them dollar-for-dollar against federal tax liability, and walk away paying less to the IRS. That alone makes them worth a serious look. But here’s what often gets overlooked and what makes these investments genuinely remarkable compared to almost anything else in your tax planning toolkit: the flexibility built into how and when the credits can be used. Can’t absorb the full credit this year? Carry it back up to three years and trigger refunds on taxes your client already paid. Think about that for a second. There are very few places in the tax code where you can go back in time and rewrite last year’s tax bill. This is one of them. Still have excess after the carryback? Carry it forward for up to 22 years. That’s not a typo. Two decades of runway to put those credits to work as your client’s passive income grows. And if circumstances change and the credits simply aren’t needed? An emerging secondary market means there may even be an option to sell them. No other common tax planning strategy offers this combination a guaranteed discount on purchase, dollar-for-dollar offset of tax liability, the ability to look backward and forward, and a potential exit if plans change. Understanding how each of these features works is what separates a good credit investment from a great one.

What Happens If You Can’t Use All Your Clean Energy Tax Credits This Year? Read More »

Perspectives on IRS Scrutiny of Captive Insurance Elections

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.

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Strict Substantiation: Why Being Right Without Proof Can Cost You Your Charitable Deduction

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.

Strict Substantiation: Why Being Right Without Proof Can Cost You Your Charitable Deduction Read More »

The Growth-Minded Accountant: Rethinking Your Role in Client Success

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.

The Growth-Minded Accountant: Rethinking Your Role in Client Success Read More »

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