In modern enterprises, workflows are essential to automating business processes. During their execution, workflows need to interact with users using a mechanism called dialogs to deliver information and collect input that is required for further decision-making in the workflows. Information delivery and input collection by enterprise workflows is often a time-sensitive matter. Thus, dialogs have to be communicated to users in a timely fashion, which necessitates sending dialogs to user communication endpoints that permit the recipients to quickly, effectively, and conveniently view the information and provide the requested feedback. The proliferation of communication devices and clients among enterprise users implies that the content and rendering of dialogs has to be tailored to a large number of endpoints and preferably by middleware. This customization poses several challenges to developing and maintaining a manageable, extensible, and flexible middleware mechanism for synthesizing dialogs from specific decision points in enterprise workflows. In this paper, we first describe the challenges associated with context-sensitive dialog synthesis. We discuss how we applied templatized model transformation techniques to automatically synthesize dialogs in enterprise workflows. We show how our templatized transformation approach supports the evolution of communication endpoints and system requirements with a minimum of downtime and invasive design changes. We demonstrate our approach in the context of a representative enterprise case study.