Challenges faced by formerly incarcerated individuals in the United States raise questions about our society's ability to truly provide second chances. This paper presents the outcomes of our ongoing collaboration with a non-profit organization dedicated to reentry support. We highlight the multifaceted challenges individuals face during their reentry journey, including support programs that prioritize supervision over service, unresponsive support systems, limited access to resources, financial struggles exacerbated by restricted employment opportunities, and technological barriers. In the face of such complex social challenges, our work aims to facilitate our partner organization's ongoing efforts to promote digital literacy through a web application that is integrated into their existing processes. We share initial feedback from the stakeholders, draw out four implications: supporting continuity of care, promoting reflection through slow technology, building in flexibility, and reconfiguring toward existing infrastructure, and conclude with a reflection on our role as partners on the side.