The orchestration of technology-enhanced learning situations (especially collaborative ones), that involve both Virtual Learning Environments and Web 2.0 tools (what some authors call Distributed Learning Environments, or DLEs) is often complex and burdensome, given the heterogeneous array of resources involved. In this paper we explore how GLUE!-PS (a system for the deployment and run-time management of learning designs across DLEs) supports orchestration, through its teacher usage in three authentic university courses and one teacher workshop. Our mixed methods evaluation reveals that GLUE!-PS supports multiple aspects of orchestration, especially the efficient implementation of teacher learning designs, the ability for useful and intuitive adaptations in run-time, and its adequacy to pragmatic restrictions that teachers face in authentic settings. Aside from the implications for the evaluated system itself, this article discusses the need for evaluations that address orchestration’s multiple facets, and provides a practical example of such multi-faceted evaluation of educational systems, in order to assess their potential for adoption and sustainability in authentic settings.