Social networking sites have become one of the most widely used social media applications, especially among college students. Unfortunately, students often post content on these sites which could be viewed as inappropriate. This is especially true when considering that employers now use social networking sites to perform background checks on job candidates. Although research has shown that students are aware employers may be viewing their profiles, they continue to post inappropriate content despite the possible negative consequences. This “posting paradox” needs to be examined so we can better understand the factors behind the phenomenon. Towards that goal, this paper draws on existing research to propose a new model of inappropriate posting. The model describes how time to graduation, online image concern, privacy concern, and trust in technology affect a student’s decision to post inappropriate content. After developing the model, the paper ends with a discussion of areas for future research.