Penalties for procrastination in tax matters can be somewhat harsh. Judge Albert Lauber of the United States Tax Court gave us some lessons on the topic earlier this year. The “strategy” of over withholding so that you can file your return whenever the spirit moves you rather than by the due date has a serious downside. The statute of limitations will not work in your favor, but it will work against you. It is a little like you are playing in a chess tournament and you and your opponent are staring at the board. Your clock is ticking and theirs is not.

I saw a meme that said, “accountants go on vacation just so they can work from another location.” This might be true. So maybe, just maybe you can write your vacation off on your taxes. But on a serious note, this is a question that taxpayers have. “Can I write off my vacation on my taxes?” I hate to blame everything on the internet but...it is a dangerous place for taxpayers. There is an infamous Tik Tok video turned reel that has found its way into my DMs and e-mail inbox several times. I’m often amused by the bad tax advice that goes viral online. The comments tend to make me giggle or give me cause for concern. This particular video gave me more cause for concern. The main reason it did this is because of the amount of tax professionals that shared in agreement. I’m all for advertising on social media but often we must be careful as tax professionals. We have certain ethical obligations that unfortunately do not apply to other industries. We do not want to mislead taxpayers for “likes” or potentially going viral. Let me get to the details of the video. A tax professional whose credentials I won’t mention, was sharing how taxpayers can use their entire family vacation as a write off on their Schedule C. Rightfully so, this made taxpayer’s ears perk up. Why not kill two birds with one stone, right? What should not have happened was tax professionals sharing the video with filling in the blanks. I know you would never do that, and that’s why you’re here. To find out what parts of travel your client can write off on their taxes. So, let’s look at what constitutes something being a business expense. Then we’ll look at the due diligence you should take to make sure their travel and meal expenses are legitimate.

The IRS loves to issue cryptocurrency guidance when it’s the most inconvenient for me personally. I’m not sure how they accessed my calendar, but it certainly feels like this one was intentional. I was at a tax conference over the summer to teach an introduction to crypto class immediately after lunch. I had just finished eating when my phone started blowing up. The IRS published a new Revenue Ruling on Staking, 45 minutes before I was to teach about it. I read the six-page document, tried to digest it, and considered how I needed to adapt my material on the fly. Another frequent (but not to be named) Tax Box contributor present at the conference teased me about the situation I found myself in. The class went fine, though, because even with a surprise ruling, the IRS didn’t really say anything surprising. In typical IRS fashion, it also created more questions than it answered.

There was a recent IRS memo from an associate chief counsel that should be shocking but actually isn’t. Promoters have for many years been hawking a “copyrighted non-grantor irrevocable complex discretionary spendthrift trust,” which purported to avoid capital gains tax. You could learn about it on TikTok. It “worked” by citing Section 643(a)(3), which excludes capital gains allocable to corpus from distributable net income. You and I both know that DNI is not taxable income, but not everybody who learns the tax law from TikTok has caught onto that subtle point yet. Although I have never encountered anything as egregious as the “copyrighted, etc, etc, trust” I have seen a lot of problems with trusts over the years (and partnerships and SALT – don’t get me started). Much of it has to do with working under a lot of pressure. Often, the things that are wrong end up not mattering all that much, but I get a little frightened, because maybe one of these days the IRS is going to start getting its act back together. If it does, I think things may be a little shocking to practitioners who have grown up in an environment where enforcement has been progressively gutted.

Tax reporting of overseas accounts has always been an extra chore for some American taxpayers. Now they might have to play a guessing game as well after the Supreme Court’s Bittner decision early this year. The case is a prime example of how taxpayers with international holdings might wrest better tax judgments in the future.

The latest Federal Tax Court news, updates, and hot topics!

The astronomical costs of a disability can extend beyond extra therapy and special equipment to, potentially, a lifetime of lost earnings. There is some help. The federal government has tax deductions and credits connected with raising a child with special needs, for instance. And though historically a trust has been only financial avenue to care for a disabled loved one, another vehicle is gaining traction. Many tax and financial moves in this area come down to one question that’s unique to this planning: Will money interfere with a disabled person’s ability to get indispensable government benefits?

Remember back in the day when having your tax and accounting software in the "Cloud" was the newest, coolest thing? Even if it took us 10 years to realize that the "cloud" just meant someone's server somewhere else? Similarly, have you noticed that our tax and accounting products have a sprinkling of AI now? And if they don't, they're talking about how they'll be AI-ing soon? (And if they're not talking about it, do we even want them in our toolbox?) Let's chat about what it means to have "AI Inside", especially with the rise of tools like ChatGPT and Bard. The "AI Inside" label is becoming ubiquitous but can mean many things, so let's discuss. I'd hate for you to get excited about an AI feature only to discover that you can access it via one of the widely available Generative AI (GenAI) tools (ChatGPT, BingChat, Bard, Claude, etc.). While this new technology has fundamentally shifted everything, what does it mean for us as tax professionals? On this journey of exploring what "AI Inside" really means, we're going to discuss what's going on under the hood. We'll also dive into why creating a fully functional "TaxGPT" is challenging right now. (Notice I said "right now"). Finally, we can look at what "AI Inside" tools would be handy, even if you CAN get that functionality out of the regular ol' GenAI applications. In the end, you'll know whether to be impressed or pass. And, even more importantly, you'll know whether to spend the extra money on those tools.