We’ve written on this topic many times,[1] but it’s worth repeating as it routinely costs taxpayers their charitable deductions. Charitable contributions must be properly substantiated in accordance with IRC Section 170 and the related Treasury Regulations. At issue in this case is the contemporaneous written acknowledgment required for cash donations more than $250 which must…
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In a recent case out of the Tax Court, a surviving spouse’s Estate was denied the portability of the Deceased Spouse’s Unused Exclusion (“DSUE”) from the decedent’s spouse who had passed away two years before the survivor.[1] The Estate Tax Return (“706”) for the decedent’s spouse, while filed, was not “complete and properly prepared” and…
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In Beleiu v. Commissioner, T.C. Memo. 2025-70, the Tax Court sustained civil fraud penalties under Internal Revenue Code (“IRC”) § 6663 against the taxpayer for tax years 2012 through 2014. While the deficiencies themselves were not disputed by the time of trial, the heart of the controversy centered on whether the underpayments stemmed from fraud.…
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Often, the value of assets can determine tax consequences. This applies in a number of areas including charitable donations, asset allocation on sale transactions, income tax on liquidation of a corporation, gift tax, and estate tax. Because the value of assets determines the amount of tax payable in these and other situations, it is critically…
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A recent Tax Court decision underscores an increasingly rigorous examination of Section 831(b) microcaptive insurance arrangements.[1] This ruling may be insightful to taxpayers considering or currently operating microcaptives, has broad implications for businesses seeking legitimate tax incentives created by Congress. Overview of the Case The case at hand involves the Internal Revenue Service’s (“IRS”) rejection…
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With the filing deadline for individuals to file their income tax returns approaching and people becoming more acutely aware of how much in taxes they will pay for the last year, now, perhaps more than other times of the year, I receive comments from people about “starting an LLC to reduce taxes,” or “having expenses…
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A recent Tax Court opinion sheds light on how unauthorized withdrawals from a jail food account were treated for federal tax purposes.[1] An Alabama sheriff found some unexpected relief when her unauthorized withdrawals, totaling $155,000 from a jail food money account were treated as impermissible, albeit genuine loans, and not embezzled income, subject to taxation.…
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As I have written about previously[1], if a Tax Court petition is not timely filed, the Tax Court will generally[2] lack jurisdiction to hear such petition.[3] In the cases mentioned in my previous article, taxpayers’ petitions were dismissed for lack of jurisdiction despite the taxpayers having good excuses, such as (1) the taxpayers mailed their…
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The recent Tax Court decision in McDougall v. Comm’r, 163 T.C. No. 5 (2024) provides important insights into the intersection of Qualified Terminable Interest Property (QTIP) trusts and the associated gift tax implications. This article delves into the case’s facts, legal issues, court holdings, and practical implications for estate planners and tax professionals. Factual Background…
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In a recent Tax Court opinion[1], the taxpayer Michael Shaut (“Mr. Shaut”), representing himself, contested the IRS’s determination of a tax deficiency. The court had to decide on several key issues, including whether Mr. Shaut was entitled to deductions for theft loss, legal fees, and net operating losses, as well as whether he was liable…
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