Captive Insurance: New IRS Tax Reporting Regime Potential for Penalties and Examinations

Friday, December 9, 2016
12:00 PM to 1:00 PM ET

Price: $224 Webinar


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On November 1, 2016, the Internal Revenue Service ("IRS") issued Notice 2016-66 identifying certain transactions relating to small captive insurance companies as a "transaction of interest." Prior to this notice, the IRS had identified certain small captives as amongst its list of "Dirty Dozen Tax Scams." Also, the IRS has been actively examining captives and their owners and litigating cases in the U.S. Tax Court. The new "transaction of interest" designation throws small captive insurance company transactions into a tax reporting regime that can potentially lead to significant penalties and IRS income tax and promoter examinations. The filing deadline is January 30, 2017.

Please join Rachel L. Partain, Charles M. Ruchelman, Christopher S. Rizek, and Mark D. Allison for this 1-hour webinar designed to educate CPAs on how to navigate the new reporting requirements and identify pitfalls for their clients.

Educational Objectives:
• A general understanding of the IRS disclosure regime for transactions of interest (TOI) under Internal Revenue Code and Treasury Regulations for transaction participants and advisors.
• A general understanding of the penalties for failure to disclose a TOI under Internal Revenue Code and Treasury Regulations for transaction participants and advisors.
• Specific information about IRS Notice 2016-66 including who must disclose (participants and advisors), how one discloses, where the disclosures are sent, and the deadlines for the disclosures.

Who would benefit most from attending this program?
In house and advisory practitioners in contacts in the federal, state and accounting space.


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Rachel L. Partain, J.D., LL.M., is a Member in Caplin & Drysdale’s New York City office, where her practice focuses on representing high-net-worth individuals (HNWIs), corporations, and TEFRA and other partnerships in complex federal and state tax controversy and litigation matters.  She provides skilled counsel to clients involved in examinations, appeals, tax and bankruptcy litigation, collections, compliance reviews, and internal investigations. Moreover, Mr. Partain partners with clients to develop policies and procedures that help reduce their risks and enhance their business operations.  Her experience includes representing captive insurance arrangements involving income tax and federal excise tax (FET) issues.


Charles M. Ruchelman, J.D., LL.M., is a Member in Caplin & Drysdale's Washington, D.C., office, where he concentrates his practice in tax litigation and controversies with the Internal Revenue Service and other tax authorities. He also represents clients in general tax matters.   Mr. 
Ruchelman has extensive experience in resolving tax matters at all stages of tax disputes including IRS examinations, IRS appeals, post-appeals mediation, trial court litigation, and appellate litigation. He has litigated cases in the U.S. Tax Court, various U.S. district courts, and the U.S. Court of Federal Claims.  Mr. Ruchelman has represented clients before the IRS examination division, IRS Appeals, or in court involving the following substantive tax issues: foreign account and asset reporting, IRS collection matters, family limited partnerships, contributions of conservation easements; estate and gift taxes, residency issues, restricted interest, employee benefits, and tax shelter disclosures. He also has considerable experience with respect to IRS examinations of partnerships and LLCs.


Christopher S. Rizek, J.D., LL.M., is a Member in Caplin & Drysdale's Washington, D.C., office. He also serves as General Counsel to the firm. In 2014, he was listed in the elite "Leading Lawyer" list for Tax Controversy by The Legal 500.  Mr. Rizek represents taxpayers in all types of federal civil and criminal tax controversy matters. He also guides clients through IRS audits, prepares administrative claims and protests of IRS actions, and litigates tax and tax-related cases in U.S. district and appellate courts, the U.S. Court of Federal Claims, and the U.S. Tax Court. In recent years, he has represented numerous financial and professional firms in connection with IRS examinations of tax shelters and related compliance and professional ethics issues.


Mark D. Allison, J.D., LL.M., is a Member in Caplin & Drysdale's New York office. Mr. Allison's practice involves complex federal, state, and cross-border tax controversy and litigation matters; related civil, criminal, and regulatory proceedings; and internal investigations. He represents multinational corporations, financial institutions, and high net worth individuals and professional athletes in proceedings before the Internal Revenue Service, the U.S. Department of Justice, the U.S. Attorneys' Office, and other government regulators, with substantial industry experience in financial services, healthcare, utilities and infrastructure.