In this paper we present the results of an exploratory study that examined the use of text mining and text classification for the au-tomation of the content analysis of discussion transcripts within the context of distance education. We used Community of In-quiry (CoI) framework and focused on the content analysis of the cognitive presence construct given its central position within the CoI model. Our results demonstrate the potentials of proposed ap-proach; The developed classifier achieved 58.4 % accuracy and Co-hen’s Kappa of 0.41 for the 5-category classification task. In this paper we analyze different classification features and describe the main problems and lessons learned from the development of such a system. Furthermore, we analyzed the use of several novel classifi-cation features that are based on the specifics of cognitive presence construct and our results indicate that some of them significantly improve classification accuracy. 1