Persistent gaps in technology literacy skills between students of differing socioeconomic backgrounds over the past two decades (even despite cases of parity in technology resources (Subramony, 2007) amongst poor and affluent students) have necessitated that researchers now look beyond monetary funding as the primary reason for the existence of the Digital Divide. Rather than looking to quantitative measures of students’ technology skills to identify potential areas for skill remediation or special services, some scholars have adopted a sociocultural approach to the problem to examine how the circumstances of technology-related classroom activities influence teachers’ technology integration strategies, and the ways in which students use technology for learning. This case study will follow four non-dominant high school students in a laptop school to examine how the conditions of activity – institutional structures, the teacher’s skills, attitudes, and beliefs about technology, the tools students use to accomplish tasks, etc. – influence the development of agency and one’s ability to use technology for academic and personal growth. Field notes, interviews, and video recordings were analyzed using a constant comparative method, drawing on the tenets of Activity Theory (Engeström, 2001) to identify tensions that hinder students’ use of technology.