This article explores a variety of opportunities and challenges with the use of cyberspace countermeasures. It critically assesses a set of conditions under which countermeasures can be an appropriate means of offensive cyber: limited aim of defense and deterrence, protection of critical infrastructure, and compliance with rules of behavior. Here, the article shows that countermeasures must be taken for the purpose of active defense and deterrence. Second, they can be appropriate as a means of defending critical infrastructure. Finally, they should be executed by state actors who comply with existing principles of cyberspace behavior. While cyberspace countermeasures can become a socially accepted, legitimate means of active defense and deterrence, the article shows that there are several challenges connected with each of these conditions. For one, there are various degrees of feasibility about what conditions are appropriate for countermeasures. The article also discusses inherent problems in the application of international law, from which rules of engagement are drawn, to cyberspace. The challenges are hard to solve, which may explain why it has been so difficult for the international community to produce a set of agreeable criteria for active defense measures.
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