This paper presents an in-depth examination of the use of simulations in economic cybersecurity decision-making, highlighting the dual nature of their potential and the challenges they present. Drawing on examples from existing studies, we explore the role of simulations in generating new knowledge about probabilities and consequences in the cybersecurity domain, which is essential in understanding and managing risk and uncertainty. Additionally, we introduce the concepts of “bookkeeping” and “abstraction” within the context of simulations, discussing how they can sometimes fail and exploring the underlying reasons for their failures. This discussion leads us to suggest a framework of considerations for effectively utilizing simulations in cybersecurity. This framework is designed not as a rigid checklist but as a guide for critical thinking and evaluation, aiding users in assessing the suitability and reliability of a simulation model for a particular decision-making context. Future work should focus on applying this framework in real-world settings, continuously refining the use of simulations to ensure they remain effective and relevant in the dynamic field of cybersecurity.