The implementation of a tobacco-free policy is the leading recommendation among health institutes for reducing the harms associated with tobacco exposure–for both smokers and nonsmokers–on college campuses. Despite the health benefits associated with tobacco-free policies, compliance with these policies remains a serious challenge on college campuses. Interventions aimed at increasing smokers’ willingness to comply with tobacco-free policies are essential for improving public health. Guided by the theory of planned behavior (TPB), the purpose of this study was to (a) investigate the factors associated with tobacco-free policy compliance among undergraduate students and (b) design and evaluate a theory-based campaign aimed at increasing compliance with a tobacco-free campus policy. To achieve these aims the current study was conducted in two phases. Phase One was a qualitative investigation that analyzed focus group data related to messaging strategies for increasing tobacco-free policy compliance. Phase Two was a quantitative investigation that used survey data to explore variables associated with tobacco-free policy compliance and to test the effectiveness of a campus-wide print-based campaign. Results from Phase One suggest various ways to target the TPB variables in messages in order to improve tobacco-free policy compliance. Results from Phase Two suggest the psychological variables and the physical variable of nicotine dependence are not related to tobacco-free policy compliance behaviors; however, social variables, quit attempts, and daily cigarette use are predictors of compliance behaviors. Similarly, the TPB variables had mixed results for relating to tobacco-free policy compliance behaviors. In addition, the campaign materials were supported as effectively improving tobacco-free policy compliance behaviors, both through individual level survey reports of compliance and observed compliance behaviors on campus. Although the campaign materials were designed around the TPB variables and were supported for improving compliance behaviors, above average campaign exposure was only found to improve normative beliefs from pre- to post-intervention. In addition to theoretical and practical implications offered from this study regarding tobacco-free policy compliance behaviors, this study also provides critical insight into the current compliance behaviors on the University of Kentucky’s campus.