The study presented constitutes the first step in a research project aiming at gaining more insight into the processes of creating educational materials through a collaborative design space. Additionally, it focuses on the possibilities of and challenges involved in creating valuable and meaningful educational materials drawing on teachers’ remix practices. The purpose of the study is to investigate how teachers' collaborative interaction with educational tools may influence ongoing improvement of the courses and materials included in design of contextualized learning paths. By taking our point of departure in existing theories and knowledge, we designed a triangulated methodology using a combination of questionnaires, interviews and user behaviour data focusing on the use of the CourseBuilder as a collaborative space. The article focuses on the possibilities and barriers of developing a collaborative design space that enables a (re)design of digital educational materials which looks at teachers’ interest in: 1) designing their own teaching materials, 2) working professionally with the redesign and remixing of materials from many different sources, and 3) adapting them to the many contexts in which materials of this type are included. This article should be seen as a step towards a deeper understanding of opportunities and challenges within teachers' cooperation on designing, sharing, redesigning and resharing teaching materials. It shows that there is a high degree of acceptance of digital teaching materials among teachers of upper secondary schools in Denmark. Furthermore, there seems to be a collaborative culture, where the majority of teachers indicate that they already collaborate professionally regarding course planning and they see advantages connected with these practises. In prior research, factors promoting the adaptation of virtual collaboration are mentioned. These include teachers’ digital skills, professional development through courses, allocated time and integration of tools that allow teachers to enter into re-design networks with colleagues. All the institutions participating in our study show a supportive environment regarding the use of CourseBuilder. However, several factors were identified indicating that CourseBuilder is not the ideal version of a design collaborator. Although the necessary factors for a successful collaborative environment are present, somehow there seems to be a missing link in the fulfilment of CourseBuilder as collaborative design space. Put differently, there are collaborative supportive environments at the specific institutions - but the productive remix practices are not facilitated by CourseBuilder, despite the design intentions and layout.