A system for contextual loading of operating system is described. A context module forms a dynamic context of a user log in at a host. The context mapper identifies a container corresponding to the dynamic context and determines whether the container is present in a local container cache of the host. In response to the container being present in the local container cache, the container is presented at the host. In response to the container being absent from the local container cache, the container is retrieved from a container store and presented at the host.