In this study, the enactment of information security risk management by novice practitioners is studied by applying an analytical lens of security-related stress. Two organisations were targeted in the study using a case study approach to obtain data about their practices. The study identifies stressors and stress inhibitors in the ISRM process and the supporting ISRM tools and discusses the implications for practitioners. For example, a mismatch between security standards and how they are interpreted in practice has been identified. This mismatch was further found to be strengthened by the design of the used ISRM tools. Those design shortcomings hamper agility since they may enforce a specific workflow or may restrict documentation. The study concludes that security-related stress can provide additional insight into security-novice practitioners’ ISRM challenges.