Information systems (IS) and software engineering (SE) have shared the domain of systems and software development for several decades with too little overlap in practice and research. The IS school has largely focused on in-house systems, concentrating on the human-computer aspects of systems development while SE attempts to apply engineering principles and methods to the production of software systems. However the fields collide where new, Web-based systems share both in-house usage and external commercial software characteristics. In this paper, the origins and the development of education of both fields are explored – then various aspects are compared and contrasted. If, as it would appear, recommended development methods are ineffective or simply not being used, is a new understanding of development practice that finds expression in creativity and improvisation the way forward, or is this just a new engineering problem to be solved? The authors conclude that we need fast and flexible methods that go beyond new SE techniques for the Web, reflecting the business imperative to quickly produce high-quality robust systems in competitive environments. Web-based systems development should be contextualized within IS theory - learning from the rigour of SE - but viewed definitively as part of a larger socio-technical system.