System operation is about setting up or changing a target system and/or its environment for purposes such as installation, upgrade, or reconfiguration. A system operation process may be executed by scripts, operations tools, code (as in “infrastructure as code”), or humans, usually based on some specification. A large amount of system downtime is caused by failures during a planned system operation or an operator incorrectly responding to a small initial error. With the rise of the Development-Operations (DevOps) and Continuous Deployment (CD) movements, the speed and frequency of system operation processes, the automation of these processes, and the possibility of concurrent and conflicting execution of several operations processes are all increasing. In the meantime, large-scale use of Infrastructure/Platforms as Services (IaaS/PaaS) and resource sharing in virtualisation introduce more uncertainties into the environment. Dependability and security issues can come from anywhere in the process – the specification, the code/scripts/tools/human involved, the target system, or the environment. Failures need to be prevented, detected, diagnosed, recovered from, or tolerated in the context of system operation processes. The goal of the workshop is to bring together researchers from academia and industry to discuss dependability and security issues of system operation and techniques to reduce the downtime caused by these issues.