This paper addresses the question of determining the optimal timing of interventions in information security management. Using utility theory, we derive the limiting condition under which, given a potential or realized risk, a decision to invest, delay, or abandon can be justified. Our primary focus is on the decision to defer costly deterministic investments, such as the removal of a service or implementation of a security patch, when the costs associated with future security vulnerabilities are uncertain. We outline an investment function with irreversible fixed costs that introduces a rigidity into the investment decision-making profile. This rigidity introduces delay in the implementation of security measures, resulting in cyclical investments in information security, as the decision-maker determines the optimal investment horizon. We therefore show that cycles emerge endogenously given the policy-maker's chosen trade-offs between investment and the deterioration of the system attributes.