With the surging number of digital devices penetrating our daily routines, the risks inherent to cybersecurity—the protection of data on digital products connected to the Internet—have also increased since these devices (e.g., connected home devices, personal monitoring) collect, process, analyze and store users’ sensitive personal information. Thus, there is a pressing need to assist users in being aware of and dealing with potential cybersecurity threats. With the proposition that fulfilling the need starts with developing an in-depth understanding of the user behaviors in the context of cybersecurity, an exploratory study was conducted that employed three mixed qualitative and quantitative research methods—a trend analysis, an interview study, and an online survey study. The paper reports the user characteristics on (1) awareness levels of cybersecurity issues, (2) uses of digital devices, and (3) means of dealing with the privacy issues in product use. The results of the studies were translated into eight personas that systematically reflect distinct characteristics of users, which can help designers empathize with their potential users vulnerable to cybersecurity risks.