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This working paper examines how the unique structural conditions of cyberspace, such as anonymity, asynchronicity, normlessness, and a lack of non-verbal cues, may influence one’s deviant experiences on the internet in ways that are different than in face-to-face environments. Specifically, I revisit a concept called “cyber-psychopathy” that was derived from a previous pilot study (Nevin 2015), which represents the hypothesized dissociative expression of 'dark' personality traits when interacting with others online. I propose extensions to this concept in terms of its role as a mediator between the structural characteristics of the internet and various forms of online deviance. Furthermore, I suggest how this idea can operate alongside existing criminological theories, while discussing the possible value of context-congruent theorizing in which explanations of online deviance are developed or applied with explicit consideration of the internet context