Cybersecurity planning supports the selection of and implementation of security controls in resource-constrained settings to manage risk. Doing so requires considering adaptive adversaries with different levels of strategic sophistication in modeling efforts to support risk management. However, most models in the literature only consider rational or nonstrategic adversaries. Therefore, we study how to inform defensive decision making to mitigate the risk from boundedly rational players, with a particular focus on making integrated, interdependent planning decisions. To achieve this goal, we introduce a modeling framework for selecting a portfolio of security mitigations that interdict adversarial attack plans that uses a structured approach for risk analysis. Our approach adapts adversarial risk analysis and cognitive hierarchy theory to consider a maximum-reliability path interdiction problem with a single defender and multiple attackers who have different goals and levels of strategic sophistication. Instead of enumerating all possible attacks and defenses, we introduce a solution technique based on integer programming and approximation algorithms to iteratively solve the defender’s and attackers’ problems. A case study illustrates the proposed models and provides insights into defensive planning. Funding: A. Peper and L. A. Albert were supported in part by the National Science Foundation [Grant 2000986].