Expenditure on Web-based initiatives has grown rapidly over the last five years, with a growing trend towards integrating these systems into the core business of many organisations. The architecture of these systems, however, tends to be quite complex – merging both a complex information architecture with a sophisticated technical architecture, with both being contextualised within new business models. An important key in achieving more effective Web system development within this rapidly changing environment will be a design approach that facilitates the creation of architectures that actively encompass both functional and informational elements, and which links both to the business model in a way that creates strong cohesion. This, in turn, requires both an appropriate architectural modelling language (particularly one that links the technology to the business model) and a process for carrying out the architectural design. In this chapter, we discuss both these aspects, looking at a model of Web systems that emphasizes the links between the various architectural elements and process-level support for design activities.