All Articles - Think Outside the Tax Box

CURRENT EDITION

By Peter J Reilly CPA

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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The IRS in 2025: A Snapshot of Reality

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.

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Client Alert

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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Your Website Isn’t Broken—Your Messaging Is

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.

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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

When TikTok Tax Hacks Backfire: Helping Clients Misled by Social Media Scams

Jessica, a self-employed consultant, was thrilled when she found a viral TikTok video promising a “little-known” tax trick. The video claimed she could get a huge refund by claiming a special Fuel Tax Credit and even writing off her family’s beach vacation as a business expense. Following the advice, Jessica filed an amended tax return and waited eagerly for a windfall. A few months later, instead of a refund check, Jessica received a stern IRS notice. Her so-called credits were disallowed, her refund was denied, and she now faced penalties. Jessica isn’t alone. Every tax season, well-intentioned taxpayers get lured by false tax advice on social media, only to end up in trouble. As tax professionals, we often meet panicked clients like Jessica who need our help to untangle the mess.

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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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