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Contemporary cyber conflict literature associates state behavior in cyberspace with the underlying technological and structural realities faced by policymakers. Consequently, interstate interactions in this human-made domain are perceived as an extension of strategic competition in the real-world. As such, strategic preferences vis-à-vis cyberspace adopted by policymakers are expected to enable the pursuit of their respective national interests. Empirical evidence collected over the last two decades, however, suggests a paradoxical situation that sees otherwise capable states restraining themselves while those with limited means investing in capabilities that generate modest strategic returns. Instead of assuming irrationality on the part of policymakers, the dissertation argues that such preferences result from the contextualization of technological and structural cues through the schematic use of strategic culture. Faced with the inherent uncertainty of cyberspace, policymakers resort to these heuristic mechanisms to derive meaning from the strategic environment in which they operate. Through pseudo-experimental cross-national wargames and a case study, the dissertation advances an ideational framework that explains the emergence of strategic preferences in response to cyber conflict. While not meant to discredit existing framework, it highlights the boundedness of human cognition that results in the utilization of these socio-cognitive mechanisms. Furthermore, this emphasizes the emerging behavioral turn in cyber conflict scholarship.