Abstract. Problem solving with experiences that are recorded in text form requires a mapping from text to structured cases, so that case comparison can provide informed feedback for reasoning. One of the challenges is to acquire an indexing vocabulary to describe cases. We explore the use of machine learning and statistical techniques to automate aspects of this acquisition task. A propositional semantic indexing tool, PSI, which forms its indexing vocabulary from new features extracted as logical combinations of existing keywords, is presented. We propose that such logical combinations correspond more closely to natural concepts and are more transparent than linear combinations. Experiments show PSIderived case representations to have superior retrieval performance to the original keyword-based representations. PSI also has comparable performance to Latent Semantic Indexing, a popular dimensionality reduction technique for text, which unlike PSI generates linear combinations of the or...