In this episode of The Edge of Risk by IRMI, we explore one of the most complex and consequential aspects of captive insurance: tax qualification and compliance. Host Joel Appelbaum is joined by Allan Autry, CPA, and partner at Johnson Lambert, who brings deep experience advising hundreds of captive insurance companies across the country. Mr. Autry breaks down the essential criteria for qualifying as insurance for federal tax purposes, clarifying how those differ from regulatory requirements. The discussion covers key tax considerations in captive formation, the impact of entity type, and scenarios where tax qualification may not even be necessary. Mr. Autry also flags common pitfalls—from failing the risk distribution test to overlooking self-procurement tax—and shares thoughts on evolving tax strategies as captive insurance companies take on climate, cyber, and supply chain exposures. Whether you're involved in captive formation, management, or as an adviser, this episode offers actionable guidance on compliance, structure, and strategic planning.