This positioning paper focuses on the selection of software for educational purposes and how the selection process may encourage usage. Computer Aided Software or Systems Engineering (CASE) tools provided an appropriate e software example for this study. The paper also seeks to examine if the use of Information Communication Technology (ICT) such as CASE can aid the students’ understanding of systems analysis and design techniques. Entity relationship modelling has been used as the primary technique. Focus groups comprising postgraduate and undergraduate students were used as the main data collection instrument supported by a pre and post assessment test. The findings provided a clear indication of which CASE tool the participants found easiest to use and which tool they were interested in using. It was further found that some tools have unique properties that may assist the user in their understanding. This paper also provides a valuable platform for defining future research in this area.