This study examines the efficacy of the Federal Trade Commission’s Red Flag initiative (2003), which aimed to curb the prevalence of seven deceptive (“Red Flag”) claims in over-the-counter weight loss product advertising. The principal component of this effort was the Commission’s promotion of voluntary guidelines which encouraged media outlets to screen advertisements for the seven Red Flag claims prior to publication. By analyzing the content of all English-language advertisement airings appearing in nationally circulated print magazines or any (local or national) TV programs between 2010 and 2011, this study evaluates the success of the Red Flag initiative as a long-term regulatory solution to deceptive advertising in this market. This study finds that the Federal Trade Commission’s Red Flag initiative, which essentially relied on industry self-regulation, failed to halt the dissemination of the seven Red Flag claims during the time period analyzed. Moreover, in response to the Commission’s actions, manufacturers appear to have engaged in offsetting behaviors and employed other creative content to imply the same “deceptive” information in their advertising, allowing them to avoid scrutiny while continuing to mislead consumers. The study explores both individual consumer and market consequences of the findings as well as raises policy implications for future regulatory action.