Context-aware user interfaces facilitate the user interaction by suggesting or prefilling data derived from the user’s current context. This raises the problem of mapping context information to input elements in the user interface. We address this problem for web applications by (i) automatically extracting a textual representation of their input elements, and by (ii) mapping context information to them using these textual representations. In this paper, we present an approach for the representation extraction task that outperforms existing ones, and we explore the potential of similarity measures for the context mapping task. 1 Motivation The increasing complexity of options available in today’s applications mostly leads to a decreased usability of the user interface (UI). To counter this effect, we need UIs that support the user in performing her tasks by facilitating the interaction as much as possible in a proactive way. Thereby, the interaction –and thus the required suppo...