Society relies upon the internet, a globally interconnected collection of networked information systems. These systems often contain critical vulnerabilities, giving states and state-sponsored groups compelling reasons to act in and through cyberspace. While state-sponsored cyberattacks can be both permissible and effective, they commonly have unintended effects: cyber collateral damage. This thesis investigates the balance between the operational effects of cyber operations and their collateral costs; the cost/benefit dilemma of offensive cyber operations. It does so by considering the potential benefit of high-impact cyberattacks, e.g. supply chain vulnerability implantation, and by using econometric methods to calculate the cost of collateral damage engendered when cyberspace is used as a domain of warfare. The thesis further presents a bottom-up analysis which shows that the economic damage caused by cyberattacks in the Russo-Ukrainian conflict 2014-2021 to be an insignificant part of the Ukrainian GDP. Finally, the thesis argues that the full cost of attacks should be measured and included in models for collateral damage estimation. Such estimates should be included into national cyber doctrines to minimize unintended effects and ensure efficient and appropriate use of cyber capabilities.