Responsive open learning environments (ROLEs) are the next generation of personal learning environments (PLEs). While PLEs rely on the simple aggregation of existing content and services mainly using Web 2.0 technologies, ROLEs are transforming lifelong learning by introducing a new infrastructure on a global scale while dealing with existing learning management systems, institutions, and technologies. The requirements engineering process in highly populated test-beds is as important as the technology development. In this paper, we will describe first experiences deploying ROLEs at two higher learning institutions in very different cultural settings. The Shanghai Jiao Tong University in China and at the “Center for Learning and Knowledge Management and Department of Information Management in Mechanical Engineering” (ZLW/IMA) at RWTH Aachen University have exposed ROLEs to theirs students in already established courses. The results demonstrated to readiness of the technology for large-scale trials and the benefits for the students leading to new insights in the design of ROLEs also for more informal learning situations.