Enterprises have focused on mechanisms to track insiders who may intentionally exceed and misuse their authorized access. However, there is an opportunity to understand why a trusted individual would want to exploit the trust and seek information with the intent of a malicious outcome. The detection of insider rogue or nefarious activities with information to which a user is already authorized is extremely difficult. Such insider threats require more deliberation than just considering it to be a problem that can be mitigated only by software or hardware enhancements. This research expects to help gain an early understanding of antecedents to such information behavior and provide an opportunity to develop approaches to address relevant character traits which could lead to a higher propensity of information misuse. This research proposes a theoretical framework and a conceptual research model to understand the antecedent factors to opportunistic information-seeking behavior of individuals. The study follows the three-essay format. Essay 1 explores the scholarly literature published about insider behavior to understand information behavior and proposes the theoretical framework for the study. PRISMA methodology was used for the thematic literature review. Essay 2 is a quantitative study of 424 university students surveyed using an online instrument for their responses to various scenarios in the context of academic dishonesty. Academic dishonesty is proposed as a proxy for information misuse. Essay 3 is a qualitative study engaging senior executives from various industries to understand their perspectives on the behavioral characteristics of individuals as they try to protect their corporate information from being misused and protect their reputation and liability from malicious use of their information.