The recent bench ruling in the bankruptcy case of Serta Simmons Bedding, LLC (Serta) by Judge David R. Jones of the Southern District of Texas finding that, in his mind, there is no ambiguity that Serta's 2020 up-tier transaction was an "open market purchase" is noteworthy for the certainty it provides on this issue notwithstanding contrary views from a federal court in the jurisdiction of the governing law of the credit agreement, and serves as a reminder on the importance of certain rules of contract interpretation. See In re Serta Simmons Bedding, No. 23-09001 (DRJ) (Bankr. S.D. Tex. Mar. 2023) (Hr'g. Tr. Mar. 28, 2023). In this article, we summarize the Serta up-tier transaction and its treatment by the courts, and provide practical guidance to market participants dealing with these type of transactions.