Tag: Law

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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Fourth Circuit Expands Potential Scope of Innocent Spouse Relief

Cases, Court of Federal Claims, Income Tax, Tax, Tax Controversy

In a significant taxpayer-favorable decision[1], the Fourth Circuit recently held that erroneous refunds of underpayment interest may constitute “unpaid tax” eligible for equitable innocent spouse relief under Section 6015(f) of the Internal Revenue Code (“Code”). Section 6015(f) provides an avenue for relief (at the IRS’s discretion) for unpaid tax or a deficiency when it would…
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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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Supervisory Approval and the Assertion of Penalties: Palmwood Holdings, LLC v. Comm’r

Charitable Giving, Income Tax, Tax, Tax Controversy, Tax Court

In Palmwood Holdings, LLC v. Comm’r, the United States Tax Court granted partial summary judgment in favor of the IRS, holding that the Service satisfied the supervisory approval requirement of section 6751(b) with respect to a civil fraud penalty first asserted in the IRS’ answer. The decision reinforces a growing body of Tax Court precedent…
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Prenuptial Agreements in Mississippi: Legal Technicalities and Practical Considerations

Estate Administration, Estate Planning

Prenuptial agreements, having long been viewed between a frame of practicality and social hesitation, have steadily gained traction as couples seek to define their financial rights and obligations before entering marriage. In Mississippi, these agreements carry significant practical and legal weight, but unlike many states, Mississippi has not adopted the Uniform Premarital Agreement Act. Instead,…
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Charitable Deductions (and Others) Must Be Properly Substantiated!

Cases, Charitable Giving, Income Tax, Tax, Tax Controversy, Tax Court

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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Loss of Deceased Spouse Unused Exclusion

Estate Administration, Estate and Gift Tax, Fiduciaries, Regulatory, Revenue Procedures, Tax, Tax Controversy, Tax Court

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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Recent Microcaptive Case Undermines Promoted Structure

Asset Protection, Business Transactions, Cases, Income Tax, Tax, Tax Controversy, Tax Court

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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