Assuming a dialectical approach to technology and pedagogy, this study explores sensemaking processes for instructors teaching in a technologically enhanced college classroom environment. Through a series of semi-structured individual and group interviews, seven instructors provided narrative accounts of the problems encountered with progressive instructional technology and their emergent strategies to make sense of and manage it. Three primary dialectical tensions were described: freedom vs. confinement, connectedness vs. fragmentation, and change vs. stability. Two related modes of sensemaking in response to these tensions were also uncovered: adaptation, involving day-to-day adjustments to non-routine failures, and reframing, entailing gradual reflection upon the instructors' roles in the classroom. Implications for the current findings are discussed.