This paper discusses the conceptual design of Digital Learning Ecosystems, which, as we argue, are becoming the foundation of next-generation Technology-Enhanced Learning systems (TEL systems). We illustrate our argument by a case study on design and development of a Dippler ecosystem. First, the framework for identifying the generations of TEL systems is described and expectations towards next generation of TEL systems are drawn from the literature review. After that, the dialectics of ongoing mainstream discourse (LMS vs PLE) is analysed and platform for reaching the synthesis is drawn. As we argue, the next-generation TEL systems are better understood if not referred as “learning environments”, but rather as Digital Learning Ecosystems. Finally, process and results of a design-based research on Digital Learning Ecosystem called Dippler is described and discussed.