This Article addresses two issues with Credit Default Swaps (CDS). First, though bankruptcy courts have correctly intuited that CDS may dictate creditor incentives, they have not fully appreciated how. Disclosure requirements in Chapter 11 are inconsistent with the actual mechanics of CDS, and therefore are unlikely to capture many of the transactions with which courts should be concerned. Second, though CDS function as synthetic debt instruments for performing credits, the economic payouts of CDS and cash bonds can deviate significantly and unpredictably for non-performing credits. To the extent that market participants deem this breakdown in equivalency a defect, rather than a feature, changes should be made to CDS' governing language-ISDA's Credit Derivatives Definitions. In addressing these issues, this Article aims to provide bankruptcy practitioners, market participants, and academics with the tools to analyze CDS, “engineered†transactions, and the implications for (i) regulatory disclosure requirements inside and outside of bankruptcy and (ii) the governing ISDA Credit Derivatives Definitions. First, I provide a detailed primer on the mechanics of CDS, paying particular attention to the auction process. Second, I analyze illustrative historical transactions, including Europcar, Codere, Hovnanian, iHeart, Supervalu, and Windstream. Third, I analyze regulatory and private contractual responses, including (i) the SEC’s recently proposed Rule 10B-1 and finalized Rule 9j-1, (ii) the 2019 ISDA Amendments, and (iii) Windstream provisions. Fourth, I analyze the relevance of engineered transactions to the “good faith†and “notice and hearing†requirements of the Bankruptcy Code. Fifth, I propose responsive amendments to (i) the Bankruptcy Rules’ disclosure requirement and (ii) ISDA’s Credit Derivatives Definitions. [ABSTRACT FROM AUTHOR]