CURRENT EDITION

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.
READ MOREHow to Avoid Losing Valuable Noncash Charitable Contributions
The rules for noncash charitable contributions defy easy summary. On the other hand, they are not rocket surgery. Moving on from the humor, if you want to sum them up in a sentence you can use Reilly’s Seventh Law of Tax Planning: Read the instructions. Specifically, you want to read the instructions to Form 8283 Noncash Charitable Contributions. There is, of course, more to it than that, but you will find a remarkable number of disallowed deductions from not following those instructions. To be fair, sometimes there are other shenanigans going on and the instruction failures are the easiest way for the IRS to attack. Nonetheless, there is nothing to say that the IRS will not use the precedents set in those cases on your client even though they are not trying to get away with anything. To get a simplified list of what to know and implement, continue reading.
Read MoreShould Your Practice Use a Client Portal?
You may know me as the “crypto guy” here at Think Outside the Tax Box. It might seem like that’s all I ever write about. But this time, I’m sneaking an article in while my editor is on vacation. Because I want to talk about using a client portal and why all tax professionals should be using one in their firms. Some firms may have dipped their toe into the digital waters out of necessity as a by-product of the pandemic. Others may have started the process long before Covid existed. According to a completely unscientific poll I ran on Twitter, 70 percent of firms are still processing returns at least partially on paper. This can mean either receiving paper documents from a client or delivering a hard copy of the completed return to the client. As the numbers from a Twitter survey are clearly biased toward firms already comfortable with digital technology, we can safely assume more accurate numbers are significantly higher. Since TOTTB refuses to provide me with a budget to run a full, comprehensive study, we’ll just have to run with my perfunctory data as well as published data from a poll Canopy conducted in 2021. Canopy surveyed more than a thousand small businesses and found that 63 percent admitted that their accountant did not offer any portal. More surprising, depending on whom you ask, is that more than two-thirds of respondents said they would be interested in switching to an accountant that allows them to use photos of their documents for easy sharing. While I’m not here to debate the issues of opening a gajillion .jpg files and how that might negatively affect my practice, the impact of using technology can improve your efficiencies, communications, and improve your workflow. To learn how, continue reading.
Read MoreThe Tax Lives of Performing Artists
Performing artists are everywhere. Whether you’re a fan or indifferent, they’re tough to ignore. They color our world with print, broadcast, and social media coverage. We have actors, musicians, newscasters, and podcasters performing live, streaming online, captured on film/radio/television, and just about everywhere in an expanding online universe. We celebrate their triumphs, empathize with their trials, feel shocked at their gaffes, and grieve for and with them. We may not think we have much in common with performers, but we do have one commonality: We’re all taxpayers! A performer’s life may seem glamorous, but it’s hard work and not always financially predictable. The tax lives of performers are complicated. They have income and expenses, but with many twists and peculiarities. Twists and peculiarities can make it both interesting and complex when navigating the Tax Code, but performing artists need tax reduction, too. Tony Nitti said, “It has to suck to make your living as an artist.” But paying taxes as an artist doesn’t have to suck when you have a great tax plan. To read more about the unique tax planning opportunities available to performing artists, continue reading.
Read MoreEthical Concerns in Using Tax Planning Software
Question: What are my ethical responsibilities when I use software to produce a tax plan? Answer: In the world of taxes, there are many ethical issues that can come into play. One area that involves judgment and expertise is when it comes to interpreting tax codes for various purposes such as taking deductions or understanding how ambiguous language might apply in certain situations – all while trying not to make any mistakes. To learn more about your ethical obligations, continue reading.
Read MoreReal Estate Developments Investments with Mineral Easements Option Course
This session will cover the basics of tax-efficient real estate strategies, specifically real estate development investments with a conservation easement option. The structure of each type of offering will be outlined in detail. The history of the laws addressing conservation easements will be discussed including an in-depth explanation on the current legislative landscape. Since the nature of each deal is driven by an underlying commodity, details outlining valuation and current market trends will be covered including the appraisal processes. Partnership voting will also be explained.
Read MoreWarning! Avoid the Latest “Dirty Dozen” Scams Identified By the IRS
Since at least 2001, the IRS has issued annual news releases warning taxpayers of scams they should be aware of and stay clear of. The release in 2001 included just eight scams but starting in 2002, the IRS expanded the list and dubbed these scams with the catchy moniker: the “Dirty Dozen.” In describing these lists, the IRS often warns taxpayers to “remain vigilant” against the scams, to not “fall prey” to them, and to “be on the lookout for” these dangerous activities. While the warnings seem to be directed to individual taxpayers, the lists sometimes include warnings of scams directed at return preparers and employers. Tax practitioners certainly need to be aware of these scams to exercise appropriate due diligence to know if any client is involved in a scam such as an abusive tax shelter, and to help educate clients about the numerous and growing number of scams many of which are designed to steal their personal and financial data and resources. This article covers the 2022 “Dirty Dozen” list. It also includes suggestions on how practitioners might use this information in tax compliance and planning and to help clients protect their identities and assets and avoid tax problems. Additional resources for dealing with the items on the list are provided. A chart listing the “Dirty Dozen” items from the start in 2001 through 2022 is included to show trends and the reality that some scams such as identity theft, phishing, return preparer fraud and frivolous tax arguments have made the list almost every year. Click here to continue reading.
Read MoreWhy Many Tax Pros Want a Stronger IRS
Early last month Adam Markowitz faced a storm of criticism over a tweet that suggested that people upset about increased IRS funding should maybe just be compliant. It got rather ugly. #TaxTwitter came to his defense despite some of us disagreeing with details of his tweet. All of my GOP friends who are worried about 87,000 IRS enforcement agents coming after the little guy... How about just don't cheat on tax returns? A fully truthful and accurate tax return is bulletproof in an audit. I never understood the fear of an IRS audit. Don't lie. Period. For somebody whose return has more than a few moving parts there is a lot of effort in putting together information for an audit. And there will usually be some things that can be viewed differently. Further you can sometimes catch the agent from hell. AFH is sure that your client is a crook and it will be hard to convince them they should go fight crime someplace else. With all that said many tax pros would still like an IRS that audits more, although they might want them to fix some other things first. To learn more about what is expected in the coming months, learn more here.
Read MoreThe Inflation Reduction Act Overview: A Brief Guide for the Non-Tax Professional
Question: How can I explain the recently passed Inflation Reduction Act to my tax planning clients? Answer: The simplest solution I've found so far is to break the Act into three components: tax credits for electric vehicles, tax credits for home improvements, and how the IRS will use the new funds allocated to them. From there, it's a simple matter of identifying some of the core concepts behind each category. To save you some trouble, I've created new client alerts to illustrate how one might do that! Keep reading to learn more!
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CURRENT EDITION

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.

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.

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.








