Many recent SEC enforcement actions involving conflicts of interest have concerned relatively arcane matters, including disclosures regarding share class selection; fee and expense practices; and acceleration of private equity monitoring fees. In contrast, a recent settlement order against the principal and chief compliance officer (CCO) of a private equity adviser involved simple self-dealing. The SEC alleged that the CCO arranged for a fund managed by the adviser to make a loan to one of the fund’s struggling portfolio companies on the condition that the portfolio company repurchase the CCO’s interest in one of the businesses owned by that portfolio company. The CCO failed to clear the transaction with the fund’s limited partnership advisory committee, resulting in penalties, a temporary bar from association with any investment adviser and a lifetime bar from acting in a compliance capacity. This case and the penalties imposed remind CCOs of the importance of disclosing conflicts of interest. This article details the facts and circumstances of the matter; analyzes the terms of the settlement; and presents insight from a former SEC Trial Counsel regarding the SEC-imposed bar on the CCO’s ability to act in a compliance capacity. See “SEC Signals Aggressive Stance on Individual Responsibility, Including Potential CCO Liability, in FY 2017 Annual Report” (Dec. 14, 2017).