ICT training courses have recently undergone some important changes. These changes are made possible by new pedagogical approaches to ICT training. As a result, the focus has changed from memorizing, recall and reproduction of knowledge to conceptual understanding of the underlying software. One of these approaches is the Herskin’s understanding-oriented ICT training method. This paper assesses students’ learning when confronted with the task of implementing this method. More specifically, it addresses critical factors of success and potential obstacles when implementing the ICT training method in upper secondary schools. It also presents teacher students’ common misconceptions and simplifications when practicing the method for the first time. Finally, the article outlines a framework for rethinking ICT training within constructivist learning environments.