Individual Strategies Archives - Think Outside the Tax Box

Individual Strategies

By Jeff Stimpson

Time for Year-End Tax Planning

This year is far from over for tax planning – for some moves, you have even longer – but now’s the time to start looking and acting on your tax tactics given your circumstances and the 2023 you’ve had so far. What you do or don’t do now could save or cost you next April.


Some Harsh Lessons on Being Late from the Tax Court

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.

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What’s at Stake? It’s Not a Loaf of Bread

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.

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Client Alert

A Supreme Court Decision Could Rewrite Penalties for Foreign Accounts

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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Tax and Financial Planning for Special Needs

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?

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Client Alert

Injured Spouse Relief

“It feels like a sucker punch to the gut.” I was on the phone with a client who was a newlywed and filing with their new spouse for the first time. They kept their paycheck withholding as single. So, they were anticipating a larger than usual tax refund. Like a lot of taxpayers, they spent their refund before they even received it. Each day, they were checking “Where is My Refund ?” and even their IRS account. Then, it happened. Code 898: Refund applied to non-IRS debt . It looked as if they wouldn’t receive that refund they already spent. Now, my client did not know what to do. Before getting married, my client’s spouse told them, “I never get a tax refund.” But they failed to mention why they never got a refund. Honestly, they did not know what their refund was paying for. We later found out that each year the Treasury Department garnished the refund for back child support. My client knew their spouse had child support but did not know they were behind on it. If you have a client in this situation, all hope is not gone. I could help my client find out what offset the tax refund. We could also get a portion of the refund back. You can do the same thing for your client. That is assuming that one spouse is not liable for the debt that offset the tax refund. The IRS calls this injured spouse relief. I’ll walk you through how you can help your client with their refund garnishment sucker punch. Yes, you can help them get their part of the refund back. Let’s start with what injured spouse relief is. Then we’ll look at who qualifies as an injured spouse and how to request injured spouse relief.

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Client Alert

Tax Rules and Due Diligence for Gambling

The vast range of taxable income and possible deductions and credits an individual may have for federal and state purposes creates a sizeable list of questions to ask clients annually. Regarding types of taxable income alone, the possible sources are almost too numerous to ask. So, is it enough for practitioners to ask for information reporting forms plus a general question about other sources of income? In 2021, the IRS expanded Schedule 1 (Form 1040), Additional Income and Adjustments to Income, changing line 8, “Other income. List type and amount” to lines 8a to 8p to highlight 16 specific types of “other income” with line 8z added for reporting any other income types. One of the specific income types at line 8b is for gambling income. Possibly the detailing of the Form 1040 other income line starting in 2021 signals that the IRS wants self-filers to be aware of what is taxable and that tax preparers should ask clients more questions. In addition to reviewing the tax rules for casual gamblers, two Tax Court bench opinions issued this year are to highlight recent gambling issues the IRS found. The opinions explored the tax gap from gambling activities along with its relevance to due diligence considerations for individuals and tax advisers.

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Pizza Party in the Metaverse

I love pizza. No, like I really love pizza. I have a pizza tattoo. I’m a member of the Rare Pizzas DAO. It is my go-to meal whenever the question “What’s for dinner?” gets asked. There really isn’t a better combination of cheese and deliciousness in the world. At least not in the flesh and blood “real” world. Loving pizza that much can clearly get oneself into trouble. I just never expected it to be tax trouble. Enter the “metaverse,” although I’m not sure if that is metaphorically or digitally. The metaverse is a term used to describe many digital environments that contain aspects of online gaming, virtual reality, social networking, and cryptocurrency. Generally, a metaverse is a fully immersive digital universe which combines elements of augmented reality, virtual reality, and the internet to create a seamless and interconnected space where users can explore, create, and engage with others in a virtual world. In the metaverse, users control an avatar, which represents the user in the digital universe and functions similar to a video game character. Avatars can be customized and accessorized with clothing and other items represented in the metaverse through NFTs. The metaverse holds the potential for new forms of entertainment, communication, commerce, and social interaction on a global scale. The metaverse economy is based on digital assets, making it possible for taxpayers to engage in a substantial number of taxable transactions without realizing it. And herein lies the crux of our problem.

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Client Alert

Tax Planning with Federal Savings Bonds

The Treasury Department offers two types of federal savings bonds, Series EE and Series I, for individuals and businesses to invest in cash savings. Until 2021, federal savings bond rates were low; however, with the dramatic increase in inflation and interest rates, interest in federal savings bonds as a savings vehicle has skyrocketed. For example, in May 2023, TreasuryDirect issued $230 million in I bonds in that one month; in May 2020, only $13 million were issued. Federal savings bonds have very favorable tax features. At the federal level, the interest earned is generally tax-deferable and sometimes entirely excluded from tax. At the state level, the interest is always entirely excluded from tax. This article will review the differences between Series EE and Series I savings bonds and the tax savings opportunities available to owners of these bonds.

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