Taxation

Tax Court Addresses Economic Substance and Disclosure Penalties in Micro-Captive Case

November 14, 2025

The Tax Court's reviewed opinion in "Patel v. Commissioner" applies the codified economic substance doctrine to micro-captive arrangements and sustains both the 20 percent noneconomic substance penalty and the 40 percent enhanced penalty for inadequate disclosure. The court outlined missing facts in the taxpayers' returns and declined to consider arguments raised too late. Read More


Bermuda Proposes Tax Credits to Offset 15 Percent Corporate Levy for Insurers and Reinsurers

September 30, 2025

Bermuda's Ministry of Finance has proposed tax credits to accompany its 15 percent corporate tax, per Reinsurance Business. The credits include substance-based incentives for re/insurers tied to jobs and local spending. The initiative aims to support Bermuda’s insurance economy, which continues to expand across captives, life reinsurers, and legacy transactions. Read More


Drake Plastics Sues IRS over Captive Insurance Premium Dispute

August 21, 2025

Drake Plastics has filed a federal lawsuit against the Internal Revenue Service (IRS) over its disallowance of captive insurance premium deductions under Section 831(b). The company argues its insurance program is lawful and essential for managing risks traditional insurers won’t cover, while warning current IRS enforcement threatens small-business risk management strategies. Read More


Whiplash—Diverging Captive Insurance Rulings and Another IRS Victory

August 11, 2025

In this commentary, Matthew Queen examines the CFM Insurance Tax Court decision, which he says diverged from Swift v. Commissioner on risk distribution but ultimately sided with the Internal Revenue Service IRS. Mr. Queen discusses what he views as conflicting judicial interpretations of captive insurance and possible future legislative or court action. Read More


Fifth Circuit Holds for IRS in Swift Captive Insurance Case

July 23, 2025

The Fifth Circuit affirmed the Tax Court’s decision in Swift v. Commissioner, rejecting the captives' risk distribution arguments and finding flaws in the pooling arrangement. The court also upheld 20 percent Internal Revenue Service (IRS) penalties for negligence and substantial understatement under section 6662 of the Internal Revenue Code. Read More