As user-generated Web content increases, the amount of inappropriate and/or objectionable content also grows. Several scholarly communities are addressing how to detect and manage such content: research in computer vision focuses on detection of inappropriate images, natural language processing technology has advanced to recognize insults. However, profanity detection systems remain flawed. Current list-based profanity detection systems have two limitations. First, they are easy to circumvent and easily become stale-that is, they cannot adapt to misspellings, abbreviations, and the fast pace of profane slang evolution. Secondly, they offer a one-size fits all solution; they typically do not accommodate domain, community and context specific needs. However, social settings have their own normative behaviors-what is deemed acceptable in one community may not be in another. In this paper, through analysis of comments from a social news site, we provide evidence that current systems are performing poorly and evaluate the cases on which they fail. We then address community differences regarding creation/tolerance of profanity and suggest a shift to more contextually nuanced profanity detection systems.