We propose a cloud contextualization mechanism which operates in two stages, contextualization of VM images prior to service deployment (PaaS level) and self-contextualization of VM instances created from the image (IaaS level). The contextualization tools are implemented as part of the OPTIMIS Toolkit, a set of software components for simplified management of cloud services and infrastructures. We present the architecture of our contextualization tools and the feasibility of our contextualization mechanism is demonstrated in a three-tier web application scenario. Preliminary performance results suggest acceptable performance and scalability.