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FEATURED CONTENT
The IRS in 2026: A Strategic Field Guide for Tax Professionals
As we head into the 2026 filing season, tax professionals are operating in an environment unlike any we have seen in recent memory: a smaller and more automated IRS, the new OBBBA, and rapid experimentation with AI-enabled tools inside the Service. This field guide is designed to separate what we know for sure from where the IRS is likely to move next, and to translate both into practical planning moves. It does not predict the future; instead, it offers a structured way to think about enforcement, documentation, and client strategy when the rules, the technology, and the politics are all in motion.
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CURRENT EDITION
Using AI In Your Tax Practice? Choose The Nuclear Option
I always know when something, especially something bad, is trending on social media. Why? Because I’m not on social media and I still hear about the issue. Lately, I’m getting disturbing reports of the cavalier attitude that many tax practitioners are taking towards the use of AI in their practices. Apparently even the IRS is catching on because in late June 2026 the Office of Professional Responsibility (OPR) sent a bulletin to practitioners reminding them of their obligations under Treasury Circular 230 and how the circular’s provisions apply to using AI in a tax practice. The bulletin includes a decent list of best practices, and I recommend reviewing the bulletin and the applicable sections of Circular 230 after you finish this article.
Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.
Structured Installment Sales Making Comeback – How Good A Tool Is It?
Structured Installment Sales (SIS) have been making a comeback. Historically low interest rates starting in 2011 made them go out of favor. Starting in 2018, insurers started coming back into offering them. MetLife expanded its SIS solution to 49 states, Puerto Rico and D.C. in 2022. You need to know about SIS and it deserves a place in your toolbox. You might not be using it as often as the toolmakers imply. I took a look at SIS in 2023 and was a little more enthusiastic about it than I am now. Let’s dig in.
SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION
Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.
