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This research is an initial investigation into the ways community-based learning increase the cognitive skills central to the exercise of the sociological imagination. In addition to identifying a means to reveal that learning had occurred, we looked for evidence that the students were mastering sociological content, especially the concepts and habits of the sociological imagination. Using a grounded theory approach, a student/faculty research team conducted a content analysis of 160 field notes from 34 undergraduate participant-observers enrolled in an academically grounded, field-based sociology course. The analysis revealed patterns of "pivot points" where students’ understanding is characterized by a noticeable jump rather than as incremental or gradual change in knowledge acquisition. These pivot points are fundamental, categorical shifts in understanding connecting particular observations to generalized theories or constructs.