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 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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In a previous article, The Often-Overlooked Benefits of Qualified Small Business Stock, I discussed the significant benefits available to taxpayers holding qualified small business stock (“QSBS”), which is defined under Section 1202 of the Internal Revenue Code (“IRC”). While significant then, the recently enacted One Big Beautiful Bill (“OBBB”)[1] amended IRC § 1202[2] to substantially…
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In a recent case issued from the United States District Court for the Eastern District of California, the Court held that a Trustee’s reliance on the advice of a CPA that no trust income tax return was due was enough to establish reasonable cause for such failure and thus avoid late payment and filing penalties.[1]…
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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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Anyone paying attention knows that stock markets have been volatile. As a simple example, the Dow Jones Industrial Average saw an increase of over 600 points (1.56%) on April 11 after dropping over 1,000 points (2.5%) on April 10. Similarly, the S&P 500 gained 9.5% on April 9, but dropped 3.5% on April 10. Generally,…
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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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Common in estate and trust planning is the gift or sale of assets to an irrevocable grantor trust[1] structured to be outside of the grantor’s taxable estate.[2] Often, such gifts or sales are made of interests in family entities such as LLC’s.[3] These entities can provide significant non-tax benefits including consolidation of assets, centralized management,…
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In a recent Tax Court decision, the Court again approached the critical issues surrounding loss deductions and tax compliance.[1] This case involves Heather and Stewart Weston, a married couple from California, who claimed a $2.1 million loss deduction on their 2017 tax return tied to failed business ventures in Indiana. The Internal Revenue Service (“IRS”)…
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