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The importance of developing and nurturing in-depth dialogue and thinking is recognized in literature as one of the key factors in establishing and maintaining successful web-based learning communities. After reviewing the literature on this issue, this research paper describes two tools developed to analyze the quality of discussion in three social science teacher on-line communities of practice. The key findings of analysis of the dialogue in each of the three communities are then reported. The paper discusses how changing the structure and facilitation of the communities improved the quality of dialogue and thinking. Finally, the paper outlines the potential of the assessment tools for improving the effectiveness of web-based learning communities.