The main purpose of TEL has been to provide an adequate support at the right time and with the appropriate means to foster the learning process by means of technology. In the last years we have provide modelization frameworks for learning content as long as improved intelligent analysis of the needs of students at an individualized level. The appearance of IoT and the new scenarios of massive courses introduces new factors and needs in the design of personalized and effective learning situations based on sensible environments, ubiquitous learning and scalable infrastructure. This talk overviews the evolution of TEL and describes some of its current challenges to provide orchestration of services and analytics that makes use of technical and semantic interoperability of the student data.