As sport properties and brands leverage the use of hashtags to expand their share of voice and audiences, they also face a host of emerging legal issues at the nexus of social media and intellectual property laws. This article examines the current potential conflict between the courts and the United States Patent and Trademark Office (USPTO) regarding the legal status of hashtags as trademarks, which provides the backdrop discussion of sport properties’ approaches to potentially infringing use of hashtags in the context of ambush marketing. The Federal Trade Commission has also initiated regulatory efforts aimed at hashtag-based promotions. Analysis of significant cases and application of a typology of hashtags to sport industry examples provides guidance to sport organizations. While typically favoring strict enforcement in matters involving intellectual property, the risk in stifling conversations stimulated by hashtags may call for more innovative tactics to achieve brand protection and consumer protection goals.