Incarcerated students often lack access to the resources and conditions, both physical and digital, that make self-directed research and research skill-building possible. Due to technical constraints – most notably the lack of internet access in most prison environments – few incarcerated students have access to research databases commonly used by students to discover scholarly content that is relevant to their coursework, research projects, and broader learning pursuits. Not only does lack of research experience have an impact on students’ ability to engage with academic work, but it also leaves students without the fundamental information and digital literacy skills that are increasingly essential for future work and continued learning. Since 2007, JSTOR, a digital library of scholarly resources, has been making strides to amend this gap in available scholarly resources and research tools by providing JSTOR access to incarcerated learners. This paper describes the work undertaken by JSTOR Labs, an experimental product development team at JSTOR, to develop an offline index of scholarly resources designed to serve the research needs of incarcerated students. Funded by the Mellon Foundation, this project yielded lessons regarding how to scale access to digital scholarly resources given the changing landscape of technology in prison, and continues to shape JSTOR’s work to help improve higher education in prison and reduce barriers for student research