The systematic development of user interfaces that enhance interaction quality by adapting to the context of use is a desirable, but also highly challenging task. This paper examines to which extent contextual knowledge can be systematically incorporated in the model-driven dynamic generation of Web user interfaces that provide interaction for operational features. Three parts of the generation process are distinguished: selection, parameterization, and presentation. A semantically enriched service-oriented approach is presented that is based on the Catwalk framework for model interpretation and generation of adaptive, context-aware Web applications. Automation possibilities are addressed and an exemplary case study is presented.