Relief from underpayment interest, failure-to-file penalties, and failure-to-pay penalties—as well as relief from IRS filing deadlines that arose during the COVID-19 pandemic—may be possible under two recent federal cases from the US Tax Court and the US Court of Federal Claims. Specifically, the recent Kwong decision indicates that the period of the COVID-19 federally declared disaster extended from January 20, 2020 to July 10, 2023. Filing deadlines that would have normally occurred and interest and penalties that would have normally accrued during this period may have been suspended under the reasoning articulated in Kwong. Taxpayer deadlines for seeking relief are fast approaching, and the time to review pandemic-era tax filings and tax accounts is now.
Recent Federal Privilege Ruling Related to AI Tools Has Implications for Routine Tax Advisor Arrangements
On February 10, 2026, Judge Jed Rakoff of the Southern District of New York ruled in United States v. Heppner that documents generated through a consumer version of Anthropic’s Claude AI were not protected by the attorney-client privilege or the work-product doctrine under the circumstances presented. The decision appears to be the first to squarely address privilege and work product claims arising from a non-lawyer’s use of a consumer-grade insecure, non-enterprise AI tool for “legal research,” as well as the potential consequences of inputting privileged information (provided to an individual by counsel) into an AI tool. However, putting the novelty of the AI context aside, Judge Rakoff grounded his analysis in traditional privilege principles: that disclosure of privileged communications to a third party in circumstances that undermine confidentiality (here, the corporation operating the AI tool) may result in waiver. And that an AI tool is just that – a tool, not an attorney. Accordingly, this decision reinforces the importance of only using properly secured AI tools with confidential or privileged information and for decisions about using AI in the privileged context to be made by those who best appreciate the risks involved: i.e., lawyers.
Fifth Circuit in Sirius Solutions Reverses Tax Court and Exempts Limited Partners from Self-Employment Tax
On January 16, 2026, in Sirius Solutions, L.L.L.P. v. Commissioner,[1] No. 24-60240 (5th Cir. Jan. 16, 2026), the U.S. Court of Appeals for the Fifth Circuit reversed the Tax Court and held that, for self-employment tax purposes, a “limited partner” means “a partner in a limited partnership that
Treasury and the IRS Release Final and Proposed Regulations on Section 892
I. Introduction
On December 15, 2025, the U.S. Department of the Treasury (“Treasury”) and the Internal Revenue Service (the “IRS”) published final regulations (the “Final Regulations”) and proposed regulations (the “Proposed Regulations”) under section 892.[1] The Final Regulations finalize, with modifications
How Relevant Is It? The Economic Substance Doctrine According to Liberty Global and Patel
I. Introduction
Should courts respect a transaction for tax purposes, when it otherwise complies with the technical requirements of the Internal Revenue Code and regulations? When should a court take the next step and consider the economic substance of a transaction and its motivations?
In two highly-awaited court decisions
New York Tax Court Approves Section 1031 “Drop & Swap” Transactions
Earlier this year, a New York City Administrative Law Judge found that the taxpayers’ sale of a tenancy-in-common (“TIC”) interest in real estate qualified for section 1031 “like-kind exchange” treatment even though the underlying property had been owned that very same day by a partnership, which distributed the
Proposed Regulations Remove Look-Through Rule for Domestically Controlled REITs
I. Introduction
On October 20, 2025, the U.S. Department of the Treasury (“Treasury”) and the Internal Revenue Service (the “IRS”) issued proposed regulations (the “Proposed Regulations”) that would helpfully revoke the current “look-through rule” for domestic C corporation shareholders to determine whether a “real
California’s Franchise Tax Board Adopts Final Regulations for Market-Based Sourcing
On September 10, 2025, California’s Franchise Tax Board (“FTB”) adopted final regulations (“Final Regulations”) amending the rules regarding market-based sourcing for sales other than sales of tangible personal property. This brings to an end the FTB’s long-running process toward formally adopting the amendments first approved in
Eighth Circuit Affirms Mayo Clinic’s “Educational Organization” Status and UBTI Refund
On July 25, 2025, the U.S. Court of Appeals for the Eighth Circuit affirmed the District Court decision holding that the Mayo Clinic is entitled to an $11.5 million refund of certain unrelated business income taxes imposed on it due to it being an “educational organization” under section 170(b)(1)(A)(ii).[1]
President Trump Signs One Big Beautiful Bill Act into Law
I. Introduction
On July 4, 2025, President Trump signed the One Big Beautiful Bill Act (the “Act”) into law.[1] The Act is similar to the Senate Finance Committee’s draft legislative text (the “SFC Bill”) (released on June 16, 2025), with several modifications and omissions. The Act’s key differences from