The ever-increasing number and severity of cybersecurity breaches makes it vital to understand the factors that make organizations vulnerable. Since humans are considered the weakest link in the cybersecurity chain of an organization, this study evaluates users’ individual differences (demographic factors, risk-taking preferences, decision-making styles and personality traits) to understand online security behavior. This thesis studies four different yet tightly related online security behaviors that influence organizational cybersecurity: device securement, password generation, proactive awareness and updating. A survey (N=369) of students, faculty and staff in a large mid-Atlantic U.S. public university identifies individual characteristics that relate to online security behavior and characterizes the higher-risk individuals that pose threats to the university’s cybersecurity. Based on these findings and insights from interviews with phishing victims, the study concludes with recommendations to help similat organizations increase end-user cybersecurity compliance and mitigate the risks caused by humans in the organizational cybersecurity chain.