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.

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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.

In the last few months, I have been getting "seems like old times" feeling as interest rates rise. They remain laughably low by the standards of my early days in the business. I can remember prime being 20%. And then there are all these issues with office rentals thanks to the aftermath of the plague. One of the nice things about a career in accounting is that while you are affected by business cycles the need for our work is somewhat continuous. I’m thinking that now might be a good time to get ahead of the curve a little and study up on a Code Section that may be coming up a lot more – Code Section 108 – Income from discharge of indebtedness. Fortunately, a recent Tax Court opinion in the case of Michael G. and Julie A. Parker can provide us with a lesson in some of the important principles in this area.

There are tax perks to filing a tax return as an ordained minister. But some of the things you’ve heard in the pool of public opinion are false, while others have a hint of truth. For example, pastors and ministers do indeed pay income taxes. Churches, on the other hand, do not but that’s a different article for a different newsletter. If you are serving members of the clergy, it is important to understand these perks. One that I see messed up the most is the housing allowance. The IRS allows ordained ministers to exclude their housing allowance from taxable income. That is if they meet certain other criteria. The complete amount the church has deemed as a housing allowance is not always the amount that the IRS allows. Even with that, the excludable amount is only from income taxes, not all tax. Ministers also have special rules and a potential exemption when it comes to social security and Medicare taxes. This is where I see many well-meaning taxpayers and even tax professionals messing up. But that will not be you or your client. We are going to look at what the minister’s housing allowance is according to the IRS. Then we will look at who qualifies for it, and how to calculate it.