This book constitutes the revised selected papers from the 14th International Conference on Risks and Security of Internet and Systems, CRiSIS 2019, held in Hammamet, Tunisia, in October 2019. The 20 full papers and 4 short papers presented in this volume were carefully reviewed and selected from 64 submissions. They cover diverse research themes that range from classic topics, such as risk analysis and management; access control and permission; secure embedded systems; network and cloud security; information security policy; data protection and machine learning for security; distributed detection system and blockchain.