Insider threat is a “wicked” contemporary organizational problem. It poses significant threats to organizational operations and information security. This article reviews insider threat research and outlines key propositions to conceptualize the interpretation of dynamic human information behavior in an organizational setting, which represent an integration of trustworthiness and human sensors’ attribution in close relationships. These propositions posit that when a focal individual violates integrity‐based trust, the group can collectively attribute a shift in trustworthiness, triggering a natural peer attribution process that assigns cause to observed behavior. Group communication can thus reflect subtle changes in a focal individual's perceived trustworthiness. The ability to understand group‐based computer‐mediated communication patterns over time may become essential in safeguarding information assets and the “digital well‐being” of today's organizations. This article contributes a novel theoretical lens to examine dynamic insights on insider threat detection.