This paper looks at the award winning designs produced in the 2004 Australian Secondary Schools Digital Design Challenge. This presentation will analyse the designs and look at graphic, 3D, architectural and web designs for both junior and senior levels, and identify what makes a design exceptional. Comparisons will be given on the way student's analysed the design brief; the software and hardware used; the differences in achievement between Government and private schools; the male and female entries. This paper will also show ways of stretching the boundaries of student's imagination by conceptualising, modelling and generating designs through effective teaching and inspiring projects.