Following several IRS victories against abusive captive insurance companies (“CICs”), the IRS on September 15, 2019 announced a pilot Captive Insurance Company Settlement Initiative (“SI”). The SI set forth a settlement offer to a very limited number of taxpayers. First, the IRS made clear that it will continue to target abusive CIC transactions in the U.S. Tax Court, but that a small group of such taxpayers (only 200 total) with at least one open year under audit have the opportunity to settle their cases on the terms outlined in the SI. This action is understandable given that it is estimated that IRS is dealing with over 500 CIC cases. The SI intends to relieve pressure on the U.S. Tax Court without litigation, conserve IRS resources, and potentially produce finality for those that accept the fixed terms. In a subsequent announcement, the IRS stated that as many as eighty percent (80%) of taxpayers that received offers under the SI accepted the terms. Although the period for accepting this SI has already expired, the IRS may expand this pilot program to make additional settlement offers that are likely to be on terms worse to the taxpayer. The IRS set out SI terms in a document attached to the September 2019 announcement titled “Micro-Captive Insurance Resolution Terms” that contains two sections and an appendix. The first two parts of this article examine the SI offer and consider how a participant who actually closes on the offer is affected. Specifically, part I of this article provides an overview of the SI’s general terms and conditions the IRS required to be met before an offer recipient could participate. Part II examines the applicable SI financial benefits and, also puts into perspective any concessions a participant had to make. This article concludes by calculating the financial results of different sample taxpayers including: (1) a taxpayer who is never audited by the IRS; (2) a taxpayer who accepts and closes on the offer; (3) a taxpayer who declines the offer. Ultimately, the goal of this article is to provide decision making context in preparation for potential future settlement initiatives.