An academic course, entitled ‘Collaborative Learning Environments’ (CLE), based on the scientific ground of Digital Systems, comprises the theoretical concepts of the collaborative learning theories and methods, based on collaborative software, digital tools and environments. Students, also as future engineers-teachers, need to integrate this theoretical background and its applications into effective instructional methods, in order to help their future students by using their acquired knowledge. The main instructional objectives of this course are: (1) to teach students how to integrate the theoretical background of collaborative learning in the development of applications, and (2) to teach methods of applying learning principles, strategies, and conditions to every day educational practice.In this paper, we use the main principles of CFT and web-based collaborative technologies to develop a “course-workshop” for prospective engineers-teachers to learn about the requirements of software applications, placed on the domain of Digital Systems. Students have to successfully transfer what they learn, to school setting, by choosing and evaluating the given conditions of an ill-structured problem methodology in the setting of teaching Microsoft applications, including MS Word. Obviously, it is not inherently easier, but the goal is to learn appropriate methods that could be applied in school programs. This course will teach the basic subjects of Microsoft application developing the best practices for schools, by using “hands-on” activities and the teaching of how to apply the acquired knowledge to everyday problems. In all of the workshops, there is an assessment of the knowledge level, and the educational scenario is adapted to students’ specific needs.