Financial Poise
Captive Insurance

Tax Stuff You Should Know-Captive Insurance: When the IRS Comes Knocking [Podcast]

In the latest episode of “Tax Stuff You Should Know,” hosts Bob Pluth and Gene Magidenko unpack the CFM Insurance decision, spotlighting the complexities of captive insurance arrangements and the Internal Revenue Service’s (IRS) scrutiny of them.

They underscore the importance of tax planning needing to correspond with economic and substantive reality, the audit risks, including those tied to refund claims, and the implications of the IRS’ Dirty Dozen list. The discussion also stresses the importance of meticulous documentation and legal compliance, and notes that reliance on qualified professional advice can help mitigate penalties.

Takeaways

  • Captive insurance companies must operate as bona fide insurance providers.
  • The IRS continues to flag certain planning strategies as high risk.
  • Taxpayers must maintain thorough documentation and comply with legal requirements.
  • Courts focus on the substance of a transaction or structure rather than its form.
  • Good-faith reliance on competent tax advice may mitigate penalties.
  • Arrangements that promise outsized tax benefits warrant skepticism.

Listen to this podcast here.

 


Tax Alert

© 2026 ArentFox Schiff LLP

This article was originally published by the National Law Review here.

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About Robert R. Pluth Jr.

Partner, ArentFox Schiff LLP Robert Pluth, Jr. is the Leader of Schiff Hardin’s Tax Practice. Bob represents taxpayers and personal, corporate, and family offices in connection with various federal and state income tax planning and tax controversy matters, including those involving complex tax accounting matters and transactional disputes. Bob also implements customized tax, succession and…

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About Evgeny Magidenko

Partner, ArentFox Schiff LLP Gene brings a strategic perspective to his clients’ matters, whether they involve tax counseling or disputes with the IRS, by drawing on his breadth of experience in the field. He also advises both for-profit businesses and tax-exempt organizations on a wide array of organizational and operational matters at all stages of…

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