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.

The IRS is not the same agency we dealt with a decade ago, or even three years ago. The pandemic accelerated operational strain, exposing long-standing infrastructure weaknesses while also prompting overdue investment and modernization. Some areas have improved meaningfully, including digital tools, faster account updates, and improved phone service during filing season. Other areas, however, feel frozen in time. Correspondence units remain slow, backlogs persist, and automated notices often fail to reflect what is actually happening on a taxpayer’s account. This article outlines the practical realities of working with the IRS in 2025, what strategies are working, what remains broken, and how to set clear, healthy expectations so you can deliver results without burning out.

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.

I recently attended a two-day marketing workshop that made me think about whether I am effectively communicating with prospects on my websites. I do an annual review of my websites and update them to keep them fresh. According to Forbes' article "Top Website Statistics for 2025", there are close to 1.2 billion websites on the internet in 2025, and only 43% of small business owners plan to invest in their website performance. Additionally, 21% of business owners report low website traffic, which can affect attracting and retaining customers, revenue growth, and overall success.

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.