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Despite an abundance of research on the problem of insider threats, only limited success has been achieved in preventing trusted insiders from committing security violations. Virtue ethics may be an approach that can be utilized to address this issue. Human factors such as moral considerations impact Information System (IS) design, use, and security; consequently they affect the security posture and culture of an organization. Virtue ethics based concepts have the potential to influence and align the moral values and behavior of information systems workers with those of an organization in order to provide increased protection of IS assets. An individual’s character strengths have been linked to positive personal development, but there has been very little research into how the positive characteristics of virtue ethics, exhibited through the character development of information systems workers, can contribute to improving system security. This research aimed to address this gap by examining factors that affect and shape the ethical perspectives of individuals entrusted with privileged access to information. This study builds upon prior research and theoretical frameworks on institutionalizing ethics into organizations and Information Ethics to propose a new theoretical model which demonstrates the influences on Information Systems Security (ISS) trusted worker ethical behavior within an organization. Components of the research model include ISS virtue ethics based constructs, organizational based internal influences, societal based external influences, and trusted worker ethical behavior. This study used data collected from 395 professionals in an ISS organization to empirically assess the model. Partial Least Squares Structural Equation Modeling was employed to analyze the indicators, constructs, and path relationships. Various statistical tests determined validity and reliability, with mixed but adequate results. All of the relationships between constructs were positive, although some were stronger and more significant. The expectation of the researcher in this study was to better understand the character of individuals who pose an insider threat by validating the proposed model, thereby providing a conceptual analysis of the character traits which influence the ethical behavior of trusted workers and ultimately information system security.