The use of class action lawsuits against large corporations over allegedly illegal tip pooling arrangements is increasingly common. This work examines the use of class action lawsuits for this type of lawsuit and analyzes two recent cases from Massachusetts and New York targeting the legality of Starbucks’ tip pooling policy under the laws of each state respectively. Both cases represent significant developments in this area of law in that each, for the first time, provides court interpretations of their respective state statutes regulating tip pooling arrangements. In light of the specific requirements of Massachusetts law, the Massachusetts case yielded a $23.5 million settlement with Starbucks. In contrast, under the different requirements of New York law, Starbucks won a significant victory on certain aspects of the case while other aspects remain unresolved. These cases represent but examples of the difficulties even large corporations encounter in complying with the vast array of applicable federal and state laws affecting their operations.