Socio-technical experiments and pilot projects have become a key governance instrument in the development of smart grids and smart cities. However, this still leaves us with the question of how to go beyond such experiments, how to learn from, aggregate and communicate experiences, or how to disseminate emerging sustainable solutions. While such challenges often are discussed as questions of replication and upscaling, a socio-technical perspective taking the entanglement of new technological configurations with socio-economic and cultural dimensions seriously adds nuance and complexity to this task. In this chapter, we develop a scheme of analysis which is sensitive to the specific institutional, geographical and stakeholder contexts of smart grid pilot projects at the site of experimentation as well as possible adoption. A better understanding of context-dependencies and knowledge translation processes may help us improve strategies for the dissemination and up-scaling of sustainable socio-technical configurations in smart cities.