Co-authored by a nonprofit administrator and an English Department faculty member, this contribution discusses the creation of a community partnership for jail-based education and writing projects. By starting small through student internships directly with the nonprofit, manageable, programmatic development followed that included classbased community writing projects, capstones, and onsite workshops engaging graduate and undergraduate students. Seeking to provide insights for new program developers as well as experienced leaders, this article reflects on the value of taking what Paula Mathieu describes as a tactical approach to partnership growth that begins with smallscale projects to maximize reciprocity and impact in order to first construct of a strong, sustainable foundation.