The current study examines the role that context plays in hackers' perceptions of the risks and payoffs characterizing a hacktivist attack. Hacktivism (i.e., hacking to convey a moral, ethical, or social justice message) is examined through a general game theoretic framework as a product of costs and benefits, as well as the contextual cues that may sway hackers' estimations of each. In two pilot studies, a bottom-up approach is utilized to identify the key motives underlying (1) past attacks affiliated with a major hacktivist group, Anonymous, and (2) popular slogans utilized by Anonymous in its communication with members, targets, and broader society. Three themes emerge from these analyses, namely: (1) the prevalence of first-person plural pronouns (i.e., we, our) in Anonymous slogans; (2) the prevalence of language inducing status or power; and (3) the importance of social injustice in triggering Anonymous activity. The present research therefore examines whether these three contextual factors activate participants' (1) sense of deindividuation, or the loss of an individual's personal self in the context of a group or collective; and (2) motive for self-serving power or society-serving social justice. Results suggest that participants' estimations of attack likelihood stemmed solely from expected payoffs, rather than their interplay with subjective risks. As expected, the use of we language led to a decrease in subjective risks, possibly due to primed effects of deindividuation. In line with game theory, the joint appearance of both power and justice motives resulted in (1) lower subjective risks, (2) higher payoffs, and (3) higher attack likelihood overall. Implications for policymakers and the understanding and prevention of hacktivism are discussed, as are the possible ramifications of deindividuation and power for the broader population of Internet users around the world.