Taxpayers challenging an Internal Revenue Service determination generally face strict deadlines for seeking judicial review. Missing those deadlines can result in the loss of the opportunity to contest substantial tax liabilities before assessment. However, a recent United States Tax Court decision confirms that certain deadlines under the federal partnership audit rules may be extended when…
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Tax lawyers routinely test proposed transactions against the technical requirements of the Internal Revenue Code. The Tenth Circuit’s recent decision in Liberty Global, Inc. v. United States[1] is a reminder that literal compliance may not always end the analysis. In Liberty Global, the court applied the codified economic substance doctrine to deny a claimed §…
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In Tooke v. Commissioner,[1] the United States Tax Court recently reaffirmed the considerable discretion afforded to the Internal Revenue Service Independent Office of Appeals (“Appeals”) when evaluating collection alternatives. Although the taxpayer presented compelling evidence of significant personal hardship, including a Parkinson’s disease diagnosis, the financial consequences of a contentious divorce, and substantial expenses associated…
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The administration of inherited qualified retirement accounts can present difficult tax and procedural issues when an estate, rather than an individual, is the beneficiary of the relevant account, which generally occurs by default when an account does not have a designated individual beneficiary. Those issues become particularly important when a decedent’s estate must divide an…
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Looking for opportunities to reduce tax liability is common. There is nothing wrong with seeking to reduce tax exposure. The late Judge Learned Hand is famous for a commonly quoted opinion from the Second Circuit Court of Appeals, saying: “Anyone may arrange his affairs so that his taxes shall be as low as possible; he…
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In a recent Private Letter Ruling (“PLR”), the IRS ruled that the relevant estate (“Estate”) was allowed a charitable deduction for income tax purposes for amounts paid or to be paid to charity during estate administration which were traceable to taxable income, a requirement for the deduction under IRC 642(c).[1] Since the ruling is private,…
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On April 22, 2026, Acting Attorney General Todd Blanche signed a final order (“Final Order”)[1] immediately rescheduling state-licensed medical marijuana from Schedule I to Schedule III of the Controlled Substances Act (“CSA”),[2] pursuant to President Trump’s 2025 Executive Order directing federal agencies to expedite the rescheduling of medical marijuana.[3] This change may materially affect the…
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A recent United States Tax Court memorandum[1] opinion provides an important reminder that life insurance policies with outstanding loans can create unexpected income tax consequences when the policy lapses or is surrendered.[2] In Sawyer v. Commissioner, the Tax Court held that a taxpayer realized taxable income when the cash surrender value of his life insurance…
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We have written before the importance of a property prepared Form 706 Estate (and Generation Skipping Transfer) Tax Return (“706”)[1] as well as the importance of a properly prepared Form 709 Gift Tax Return[2]. In our prior article discussing the 706, we highlighted a Private Letter Ruling (“PLR”) in which the Estate was granted a…
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A recent federal district court decision[1] highlights the significant risk that beneficiaries and fiduciaries may face when estate assets are distributed before federal estate tax liabilities have been fully satisfied.[2] In United States v. Karst, the court granted summary judgment in favor of the government and held that the decedent’s sons, who were named as…
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