This article explores a central issue in system design, namely whether the system should be designed to meet clients' specification of their problem, or whether that problem should be reinterpreted by the system designer in order to exploit characteristics and potential of the computer-based medium. Accepting such reinterpretation may require users to re-think their approach to their problem, i.e. to make conceptual detours. That such detours can sometimes prove highly expedient and acceptable to users is illustrated with reference to a comparison of two software packages designed for casual users. The packages shared the same application, the same user group and the same designer, but diverged in their underlying philosophy. This resulted in differences in command language, in user support and in the acceptability of the packages to the user group. Two conclusions are drawn: first that detour routes can sometimes provide a viable solution path to design problems, and secondly that there is a need to develop ways of evaluating the potential of alternative designs (whether involving detours or not) rather than continue striving for some optimum compatibility with users' initial conceptualizations.