All Articles - Think Outside the Tax Box

CURRENT EDITION

By Annette Nellen, CPA, CGMA, Esq.

Worrisome Messages Subtly Delivered Via Recent Tax Developments

Tax professionals are inundated with tax developments from all branches of the government and from all levels of government on a daily basis. Our technical tax knowledge expands weekly. Given the immensity of tax law changes in P.L. 119-21 (July 4, 2025), informally named the One Big Beautiful Bill Act (OBBBA), and the guidance we’ll continue to get over the next few years along with non-OBBBA updates, we might run out of time and bandwidth to step back and ask what additional relevance this guidance, as well as various reports issued by the government every day, mean for the well-being of our tax system. This article unpacks select tax law changes and government documents to offer four subtle messages within them. Generally, the messages don’t bode well for an effective tax and revenue system. The article ends with some suggestions on what can help improve our tax system.

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IRS and DOJ Enforcement Against Tax Professionals: Trends, Cases, and Lessons

In recent years, the IRS Criminal Investigation (CI) division and the Department of Justice (DOJ) have aggressively pursued tax professionals involved in fraud or other tax-related crimes. Certified tax planners, preparers, accountants, and attorneys who engage in misconduct are facing serious legal consequences. This article reviews notable prosecutions from roughly the past five years, highlighting enforcement trends and the types of fraud authorities have targeted. We then distill 10 key lessons from these cases – each supported by real-world examples and case citations – demonstrating how broad enforcement has impacted tax professionals. Finally, we conclude with a comprehensive list of dos and don'ts to help tax practitioners stay on the right side of the law and avoid the pitfalls that landed others in trouble.

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How to Overcome the Fear of Delivering Bad News to Clients

We’ve all been there. Breaking bad news is one of the hardest parts of being a tax professional. But avoiding these conversations only makes things worse. The good news? There are ways to make this process easier. With the right approach, you can turn these tough conversations into opportunities to build trust, strengthen your reputation, and reinforce your expertise.

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Selling a Piece of Real Estate? You Don’t Have to Pay Taxes, Even if You Don’t Use Section 1031

Overpaying on taxes puts a damper on anyone’s mood. You should be paying precisely what you owe—no less, and no more. When it comes to selling your real estate, you really don’t have to pay taxes on that sale right away. One way to avoid the taxes is by using a Section 1031 exchange, but you actually have other options. This article will show you how to take advantage of them.

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Client Alert

TAX COURT ROUNDUP – April 2025

Some new developments arose in March and some new gimmicks. The current hot topics, microcaptive insurers and syndicated conservation easements, remain on the front burner.

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Breaking Down Tax Benefits for Higher Education

With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings.

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Don’t Forget About the Refund Statute Expiration Date

Have you ever found an amazing strategy for a new tax prospect that they missed in previous years? Even worse, have you realized that you overlooked a client’s eligibility for a credit when you prepared their tax return? Not only that, but you had them make an unnecessary estimated tax payment. Well, it may not be too late for your client and prospect to take advantage of those credits for the year in question. The fate of your client isn’t sealed after filing their tax return. The IRS gives taxpayers a set amount of time to make a claim for a credit on their return. The IRS calls the date that this time sunsets the Refund Statute Expiration Date.

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Client Alert

Syndicated Conservation Easement Promoters Continue to Lose In Tax Court

The Tax Court docket has been inundated with syndicated easement cases. In 2024, the IRS was mostly winning. That trend has continued in 2025. So far there have been three IRS wins. Here they are.

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YouTube Content Strategy for CPAs: Educating and Engaging Audiences through Video Content

Video content continues to be a strategic and powerful tool for engaging audiences and establishing a brand's authority. According to VideoScribe research, 65% of people prefer visual learning. For Certified Public Accountants (CPAs), leveraging YouTube offers a rare opportunity to educate clients and prospects and entertain and connect. CPAs, accountants, and bookkeepers can address common questions, provide valuable insights, and foster trust by creating educational and informative video content that converts. Herein, I will discuss why YouTube, as a marketing tool, benefits accountants and how you can make various compelling video content to increase your reach and visibility. Let's get to it!

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