Captive Taxation: Myth Busters

December 11, 2025

Captive tax specialists explore and bust four myths concerning captive insurance companies and their federal and state income tax treatment. The panelists will examine captive tax industry trends, operational best practices, highlight recent tax developments, unpack key tax concepts, and clarify misconceptions.

Learning Objectives: After completing this webinar, participants will be able to:

  • Explain how captive insurance companies meet the federal income tax definition of an insurance company
  • Describe recent federal tax developments affecting the captive insurance industry
  • Identify common state corporate income tax filing issues relevant to captive insurance company owners
  • Apply operational best practices that promote effective coordination among regulatory, audit, tax, and finance teams within captive insurance companies

Resources

Slide Deck
Video File

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Who Should Watch

  • Captive Consultants
  • Captive Managers
  • Corporate Counsels & Attorneys
  • Insurance Company Auditors
  • Regulatory Compliance Officers
  • Tax Professionals & CPAs

Speakers

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Courtney Doherty
Director of Global Captive Management

Courtney is Director of Global Captive Management at Hylant. An active professional in the captive insurance industry since 2012, Courtney possesses a deep and detailed understanding of the captive insurance industry and prioritizes strong, meaningful relationships she builds with clients and colleagues. Like many in this industry, Courtney loves to learn, grow, adapt, and navigate emerging trends and challenges with creative problem-solving.

Conor McKenzie
Of Counsel

Conor McKenzie is a tax attorney with Downs Rachlin Martin based in Vermont where he advises businesses on a wide range of federal, state, and local tax issues, including captive insurance. Prior to joining DRM, Conor practiced for 10 years at EY in Boston, Massachusetts where he spent a significant amount of time focused on insurance tax issues. Conor holds a B.A. from Union College, a JD from the University of Connecticut School of Law, and an LLM in Tax from Boston University School of Law.

Alicia Miller
Senior Tax Manager

Alicia Miller is a Senior Tax Manager at Crowe LLP, where she leads tax services for a wide range of U.S. and international insurance clients. She specializes in federal and state tax compliance, captive structuring, and complex insurance tax matters, working extensively with single-parent captives, RRGs, association captives, and cell companies. Alicia is an active contributor in the captive industry, serving on the Vermont Captive Insurance Association’s Strategic Planning Committee and as an instructor with ICCIE. She has been recognized as a Captive Review “40 Under 40” honoree.