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 class-based 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 small-scale projects to maximize reciprocity and impact in order to first construct of a strong, sustainable foundation. Through descriptions of the evolution of this partnership, best practices for communication, addressing challenges, and expanding projects are outlined. Insights about this partnership reveal possible student-engaged activities and assignments, as well as the complexities of jail and prison writing. Reflections by students and community partners affirm a range of opportunities and the value and impact of internships, service learning, and community-writing when working directly with nonprofits, rather than with jails or prison administrators.