Building upon the work of Scenters-Zapico's (21) Generaciones, this article examines the digital literacy development and practices of two students passing through three different educational institutions on the U.SMexico border. The author makes the argument that literacy narratives such as the ones shared here are vital for complementing the work done by broader quantitative studies on the digital divide, as they document differences that may be otherwise overlooked. In exploring the very different narratives of two students transitioning through high school and into a two-year college or four-year university, this article complicates understandings of the digital divide by exploring technological divides between educational institutions and the role that gateways, external sponsors, and self-sponsorship play in students’ technological literacy development, especially when confronted with limitations on access. The discussion and findings have implications for writing program administrators as well as composition teachers and researchers, including those teaching in online environments.