It is important to address why individuals continue to engage in insecure behaviours online. Using public Wi-Fi, while commonplace, is still unsafe. The design of information campaigns and training needs a greater understanding of the attitudes and behaviours that it seeks to change. Knowing whether users realise they are engaged in unsafe practices, or have misjudged the likelihood that their unsafe behaviour will lead to negative consequences, is essential in understanding the decisions they make. Individuals may be overly optimistic, or succumb to the temptations of the moment by trading security for convenience. This research examines if particular individual differences correlate with the decision to connect to public Wi-Fi by measuring participants’ impulsivity, privacy proclivity, technical expertise, and cyber-security knowledge. Examining these variables is important, given the dearth of research on individual differences in cyber-security behaviour, and the possibility of translating any insight into actions that encourage safe conduct online.