In recent years, there has been an explosion of attacks directed at microservice-based platforms-a trend that follows closely the massive shift of the digital industries towards these environments. Management and operation of containerbased microservices is automation-heavy, leveraging on container orchestration engines such as Kubernetes (K8s). Helm is the package manager of choice for K8s and provides Charts, i.e., configuration files that define a programmatic model for application deployments. In this paper, we propose a novel methodology for extracting and evaluating the security model of Helm Charts. Our proposal extracts a topological graph of the Chart, whose nodes and edges are then characterised by security features. We carry out risk assessments that refer to the attack tactics of the MITRE ATT&CK framework. Furthermore, starting from these scores, we extract the riskiest attack paths. We adopt an experimental validation approach by analysing a dataset created from multiple publicly accessible Helm Chart repositories. Our methodology reveals that, in most cases, they have vulnerabilities that can be exploited through complex attack paths.