In the last years, increasing smartphones’ capabilities have caused a paradigm shift in the way of users’ view and using mobile devices. Although researchers have started to focus on behavioral models to explain and predict human behavior, there is limited empirical research about the influence of smartphone users’ individual differences on the usage of security measures. The aim of this study is to examine the influence of individual differences on cognitive determinants of behavioral intention to use security measures. Individual differences are measured by the Five-Factor Model; cognitive determinants of behavioral intention are adapted from the validated behavioral models theory of planned behavior and technology acceptance model. An explorative, quantitative survey of 435 smartphone users is served as data basis. The results suggest that multiple facets of smartphone user’s personalities significantly affect the cognitive determinants, which indicate the behavioral intention to use security measures. From these findings, practical and theoretical implications for companies, organizations, and researchers are derived and discussed.