Tag: sage

Tax Court Rejects Offer in Compromise Despite Extraordinary Personal Circumstances

Cases, Income Tax, Tax, Tax Court

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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IRS Provides Guidance on Dividing Inherited IRAs Through Trustee-to-Trustee Transfers

Income Tax, Private Letter Rulings, Tax

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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A Review on Listed Transactions

Charitable Giving, Income Tax, Tax, Tax Controversy

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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IRS Allows Charitable Deduction for Income Paid from Estate

Charitable Giving, Income Tax, Private Letter Rulings, Regulatory, Tax

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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From Schedule I to Schedule III: Tax and Estate Planning Consequences of Rescheduling State-Licensed Medical Marijuana

Uncategorized

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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Lapsed Life Insurance Policy Generated Taxable Income and Limited Interest Deductions

Income Tax, Tax Controversy, Tax Court

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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Improperly Prepared Estate Tax Return Costs Estate a Shot at the Marital Deduction

Cases, Estate Administration, Estate and Gift Tax, Tax, Tax Controversy, Tax Court

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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Beneficiaries and Trustees May Face Personal Liability for Unpaid Estate Taxes

Cases, Estate Administration, Estate and Gift Tax, Tax Controversy, Tax Court

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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