This research study was designed to explore the potential connections between teachers’ contexts and their instruction. Specifically, I explored how teachers perceived contextual influences on technology-related instructional decisions in secondary social studies classrooms. I defined teachers’ contexts as comprised of curricular, interpersonal, and organizational or institutional factors existing on three organizational layers, described as macro, meso, and micro. Through a multiple case study design and interpretivist perspective, I studied three cases of individual social studies teachers working in the shared environment of one high school. I viewed the teachers as curricular-instructional gatekeepers (Thornton, 2005) working in a contested classroom space (Craig, 2009). Through this lens, data generation took place at the classroom level and included interviews, observations, and artifact analysis. Data analysis was structured by the Information Ecologies framework (Nardi & O’Day, 1999) to provide a consistent approach for analysis of teachers’ decision-making within and across cases. Study findings revealed multiple contextual influences that varied in significance across cases depending on the educational orientation of each teacher. Teachers’ contexts and individual educational orientations aligned to varying degrees and resulted in unique curricular-instructional gatekeeping in each case. Accordingly, instructional decision-making regarding the use of educational technology was inconsistent across cases despite the shared environment in which the three teachers worked.