Tax Law and International Tax Law

The US Court of Federal Claims recently addressed a critical question for Canadian exempt organizations earning US-source income: can they rely on fiscal transparency rules to claim treaty benefits through investment vehicles? The court's ruling in The South Saskatchewan Community Foundation Inc. v. United States examines when charitable organizations may look through intermediary entities to access tax exemptions under the US-Canada tax treaty, with significant implications for cross-border investment

The Treasury Department has issued proposed regulations fundamentally changing how U.S. shareholders calculate their pro rata share of controlled foreign corporation income when ownership interests vary throughout the year. These regulations implement amendments from the One Big Beautiful Bill Act, introducing daily proration methodologies, mandatory year-end closings for status changes, and new elective provisions for significant ownership variances.

The Maryland Tax Court struck down the state's digital advertising tax on multiple constitutional grounds, potentially establishing a precedent for challenging similar state taxes targeting the digital economy. The decisions address fundamental questions about how states can tax digital services without violating federal law and constitutional protections.

A Connecticut Supreme Court decision demonstrates how a $13 million estate tax dispute reinforces a critical planning lesson: formal declarations of domicile carry limited weight when contradicted by an individual's actual living patterns. The case examines how spending more time in Connecticut than Florida, despite obtaining a Florida driver's license and voter registration, led to a substantial tax liability.

The IRS has issued Notice 2026-40 providing transition guidance for investors who deferred capital gains under the original Opportunity Zone program. While December 31, 2026 remains the mandatory recognition date for deferred gains, the guidance reveals a potential planning opportunity that may allow certain investors to continue deferring gains under the new Opportunity Zone regime through strategic pre-year-end transactions.

California's proposed Billionaire Tax Act would impose a onetime 5% excise tax on individuals and trusts with assets exceeding $1 billion, creating unprecedented challenges for estate planners. The retroactive application and anti-abuse provisions raise critical questions about the treatment of grantor trusts, non-grantor trusts, and beneficiary interests that deviate significantly from established federal wealth transfer tax principles.

Liability management exercises (LMEs) offer companies facing financial pressure an alternative to formal bankruptcy, but their tax consequences can significantly impact long-term value creation. Understanding how different LME structures affect cancellation of indebtedness income, tax attributes, and future deductions is essential for stakeholders evaluating out-of-court debt restructuring options.

Navigating the complex landscape of US federal income tax rules is crucial for investors and sponsors in private equity, venture capital, and hedge funds. Understanding how different investor categories—from US taxable entities to foreign pension funds—face distinct tax sensitivities can significantly impact investment returns and structural decisions when forming or investing in funds.

U.S. companies making cross-border dispute payments face unexpected tax liability when withholding requirements are overlooked. Understanding how the origin of the claim doctrine characterizes settlements and damages as FDAP income can prevent costly surprises and ensure proper tax compliance in international dispute resolution.

The IRS has issued Notice 2026-40 providing transition guidance for investors who deferred capital gains under the original Opportunity Zone program. While December 31, 2026 remains the mandatory recognition date for deferred gains, the guidance reveals a potential planning opportunity that may allow certain investors to continue deferring gains under the new Opportunity Zone regime through strategic pre-year-end transactions.

The United States cryptocurrency regulatory landscape has undergone its most dramatic transformation in history. The signing of the GENIUS Act into law on July 18, 2025 — the first comprehensive federal crypto statute ever enacted — marks a before-and-after moment for American digital asset law.

Early decisions about a start-up's legal structure can dramatically affect tax outcomes and financial returns as the company grows and reaches liquidity events. Understanding the Qualified Small Business Stock (QSBS) exemption and implementing proper structuring from the outset can significantly enhance returns for both founders and investors.