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.

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…

In Boulting v HMRC, the First-tier Tribunal (FTT) delivered a welcome decision for taxpayers on the tax treatment of a company purchase of its own shares.

The general rule is that when a UK-resident company purchases its own shares from a UK-resident shareholder, the shareholder is subject to dividend…

In a unanimous judgment, the UK Supreme Court has given final confirmation that VAT incurred on adviser fees connected with an exempt share sale is not recoverable, endorsing the Court of Appeal’s strict application of the “direct and immediate link” test. The decision brings finality to an area that had…

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…

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…

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…

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…

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…