Context-aware application and services proposing potentially useful information to users are more and more widespread; however, their actual usefulness is often limited by the "syntactical" notion of context they adopt. The recently started AMBIT project aims to provide a general software architecture for developing semantic-based context-aware tools in a number of vertical case study applications. In this paper, we focus on the knowledge management foundations we are laying for the Semantic

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... ine of the AMBIT architecture. The proposed semantic analysis and similarity techniques: (a) exploit the textual information deeply characterizing both users and the information to be retrieved; (b) overcome the limits of syntactic methods by leveraging on the strengths of both classic information retrieval and knowledge-based analysis and classification, ultimately proposing information relevant to the user interests. The experimental evaluation of a preliminary implementation in an actual "cultural territorial enhancement" scenario already shows promising results.