A web-based courseware titled junior secondary mathematics was recently developed for the provision of educational support to students-learning of mathematics- on five selected topics so far. as consultants to this government-funded project, the authors outline the background and the principles of design of the courseware. drawing on their experiences in the design process, the authors attempt to examine the issues pertaining to (I) the use of real-life contexts in the instructional design for mathematics; (ii) the interactive and exploratory learning opportunities such as games that are believed to be conducive to the construction of mathematical concepts; (iii) the notion of "self-learning" possibly enhanced by internet technologies. situated in these years of technological boom in educational provision, especially in the Asian countries/regions, the discussion on these issues highlights the tension between the prevailing instructionist approach to mathematics learning and teaching on the one hand and the various opportunities promised but not as yet fully materialized by computer technologies on the other. apart from didactical implications in terms of student activity and teacher's role, suggestions of further research are also made.