Young generations make extensive use of mobile devices, such as smartphones, tablets and laptops, while a plethora of security risks associated with such devices are induced by vulnerabilities related to user behavior. Furthermore, the number of security breaches on or via portable devices increases exponentially. Thus, deploying suitable risk treatments requires the investigation of how the digital natives (young people, born and bred in the digital era) use their mobile devices and their level of security awareness, in order to identify common usage patterns with negative security impact. In this article, we present the results of a survey performed across a multinational sample of digital natives with distinct backgrounds and levels of competence in terms of security, to identify divergences in user behavior due to regional, educational and other factors. Our results highlight significant influences on the behavior of digital natives, arising from user confidence, educational background, and parameters related to usability and accessibility. The outcomes of this study justify the need for further analysis of the topic, in order to identify the influence of fine-grained semantics, but also the consolidation of wide and robust user-models.