The goal of this research study was to investigate the implementation and evaluation of a variety of digital media and web-based solutions and their effect and contribution on the learning environment in relation to the promotion of students’ thinking skills. In particular, the objectives of the study included: an assessment of the educational value of a variety of multimedia and web-based solutions using different evaluation approaches; an investigation of the contribution of digital media in the development of an inquiry-oriented learning environment; an examination of the enhancement of students’ skills in the use of digital media, and the examination of an inquiry-oriented multimedia and web-based solution while the students, the computer and the teacher interacted to create a social constructivist learning environment. In particular, the research described in this study involved an investigation of the implementation of digital media – utilising Macromedia multimedia and web-based solutions for school project work – in a Year 9/10 Information and Software Technology (IST) elective course: Internet and Web Design. It concentrated on the subsequent assessment and impact that the software had on creating an inquiry-based situation to promote higher-order thinking skills among students completing multimedia projects for publication on the World Wide Web within a secondary classroom.