Although a large number of e-learning systems for individual learning support exist today, many of them still deal with pedagogical issues in an isolated way. In contrast, intertwining interactive system features with educational concepts allows pedagogical designs that may be considered according to their educational rationale. However, pedagogical approaches also do not provide requirements for technologies; they rather consider tools and features as predefined design parameters. Taking an interoperability point of view allows focus on the interaction between the pedagogical and the technological systems. By interpreting technology and didactic approaches as systems and ensuring their interoperability, educators are able to adapt learning experiences and technological features in a way that the overall learning system becomes personalized. A key element of the described work is an architecture that captures the design elements from both progressive education focusing on individual learning support, and the enabling web-based e-learning technologies.