Abstract Research examining cybercrime and personality is a critical, but understudied topic. From an applied perspective, such research will inform better practice in cyber defense. It will also contribute to our theoretical and practical understanding of trait expression in a relatively unstructured environment. Building on Trait Activation Theory, we predict that the unstructured environment computer attacks will elicit individual differences in decision making that can be attributed (in part) to differences in personality traits. Here we examine the varying approaches that individuals high in different Dark Triad traits and deception strategies take in executing cyberattacks. Using a hypothetical game scenario, Study 1 found that long-term mimicry deception and Machiavellianism were strong predictors of stealthy attacks, whereas narcissism and psychopathy were associated with shorter term or aggressive (i.e., “brute force”) attacks. Study 2 replicated this general pattern of results in a realistic lab simulation. The findings speak to the differential nature of the Dark Triad in the unstructured environment of cyber-attacks. These findings also contribute to our knowledge of how different attacks may emanate from individuals with different manipulative personality traits.