Captive Insurance Governance: Legal, Regulatory, and Tax Challenges

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October 29, 2026 |

gavel on a rest sitting on a gray and gold map next to a courthouse icon

As captive insurance companies evolve, maintaining effective governance and meeting legal and regulatory requirements remain essential responsibilities for captive owners. From federal tax considerations to corporate documentation and board oversight, understanding these obligations can help organizations avoid compliance problems and support long-term captive operations.

In a recent episode of The Edge of Risk podcast by IRMI, Joel Appelbaum speaks with Bailey Roese, partner at Dentons, representing the Self-Insurance Institute of America (SIIA). Ms. Roese discusses the legal considerations involved in establishing and operating captive insurance companies, including selecting appropriate corporate structures and domiciles, maintaining adequate documentation, and ensuring captives function as legitimate insurance businesses.

The conversation also addresses Internal Revenue Service scrutiny of micro-captives and the broader implications of court decisions involving captive insurance arrangements. Ms. Roese explains why the legal principles established in these cases can affect captives of different sizes and discusses the distinction between state insurance licensing and federal tax qualification. She also examines how adding new coverage or restructuring a parent organization can create additional legal and regulatory considerations.

Throughout the discussion, Ms. Roese emphasizes the importance of informed board members, consistent governance practices, and collaboration with captive managers, actuaries, legal advisors, and regulators. She encourages captive owners to remain engaged in their programs and continue building their knowledge of the industry's evolving requirements.

Hear the full conversation on Captive.com to learn how captive owners can strengthen governance, maintain appropriate documentation, understand federal tax considerations, and evaluate legal and regulatory issues that may affect their captive programs.

October 29, 2026