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The Dialogue on Dialogues workshop was organized as a satellite event at the Interspeech 2006 conference in Pittsburgh, Pennsylvania, and it was held on September 17, 2006, immediately before the main conference. It was planned and coordinated by Michael McTear (University of Ulster, UK), Kristiina Jokinen (University of Helsinki, Finland), and James A. Larson (Portland State University, USA). The one-day workshop involved more than 40 participants from Europe, the United States, Australia, and Japan. One of the motivations for furthering the systems' interaction capabilities is to improve the AI Magazine Volume 28 Number 2 (2007) ( AAAI) However, relatively little work has so far been devoted to defining the criteria according to which we could evaluate such systems in terms of increased naturalness and usability. It is often felt that statistical speech-based research is not fully appreciated in the dialogue community, while dialogue modeling in the speech community seems too simple in terms of the advanced architectures and functionalities under investigation in the dialogue community.