In the last ten years, Model Driven Engineering (MDE) approaches have been extensively used for the analysis of extra-functional properties of complex systems, like safety, dependability, security, predictability, quality of service. To this purpose, engineering languages (like UML and AADL) have been extended with additional features to model the required non-functional attributes, and transformations have been used to automatically generate the analysis models to be solved by appropriate analysis tools. In most of the available works, however, the transformations are not inte grated into a more general development process, aimed to support both domain-specific design analysis and verification of extra-functional properties. In this paper we explore this research direction presenting a transformation workflow for dependability analysis that is part of an industrial-quality infrastructure for the specification, analysis and verification of extra-functional properties, currently under development within the ARTEMIS-JU CHESS project. Specifically, the paper provides the following major contributions: i) definition of the required transformation steps to automatically assess the system dependability properties starting from the CHESS Modeling Language, ii) definition of a new Intermediate Dependability Model (IDM) acting as a bridge between the CHESS Modeling Language and the low-level analysis models, iii) definition of transformations from the CHESS Modeling Language to IDM models.