Taxation

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


831(b) Institute Urges Repeal of IRS Rule on Micro-Captives

June 20, 2025

The 831(b) Institute and industry groups are challenging new Internal Revenue Service (IRS) regulations that label many micro-captive insurance arrangements as listed transactions. They argue the rules revive issues from the vacated Notice 2016–666, conflict with the Protecting Americans from Tax Hikes Act, and unfairly burden legitimate 831(b) captives used for small business risk management. Read More


Tax Compliance and Structuring Tips for Captive Insurance Companies

June 11, 2025

Allan Autry of Johnson Lambert joins The Edge of Risk to explain tax qualification, compliance pitfalls, and evolving strategies in the captive space. Learn how federal and state standards diverge, when captives may not need tax status, and how to future-proof your structure against regulatory challenges. Read More