This thesis presents the design and analysis of Spasiba, a context-aware mobile advisor. We argue that current context-aware mobile applications exhibit significant flaws with respect to (1) limited use of context information, (2) incomplete or irrelevant content generation, and (3) low usability. The proposed model attempts to tackle these limitations by advancing the usage and manipulation of context information, automating the back-end systems in terms of self-management and seamless extensibility, and shifting the logic away from the client side. A distinguishing characteristic of Spasiba is the proactive approach to notifying the user of information of interest. In this proactive approach, the user subscribes to the service and receives content updates as the context changes. This proposed model is realised in a proof-of-concept prototype that uses a Nokia Web Runtime widget as the client application. The widget, which sports an elegant, touch-optimised interface, collects multiple context parameters to deliver high-quality results. The server-side architecture employs the publish/subscribe paradigm for managing the active users and Comet—for proactively notifying the clients of updated information of interest. IRS-III, a Semantic Web Services broker, handles the process of content generation. The prototype employs nine data sources, seven of which are open API web services and two of which are regular web pages, to deliver diverse and complete results. A simple autonomic element, implemented with the help of aspect-oriented programming, ensures partial self-management of the back-end systems. Spasiba is evaluated by means of a case study that involves a tourist couple visiting Victoria. The application assists the tourist couple with finding attractions, relevant stores, and places serving food.