Reentry programs play a crucial role in supporting formerly incarcerated individuals as they reintegrate into society. However, these programs face significant financial challenges, particularly grassroots organizations that lack stable funding streams. While larger organizations may have diverse financial resources, smaller nonprofits often rely on grants and government support, which can be inconsistent and come with restrictions. Sustainable funding remains a persistent issue, affecting the scope and effectiveness of reentry services. This chapter explores the financial hurdles faced by reentry programs, the competition for limited funding, and the need for innovative financial strategies to ensure long-term sustainability. Addressing these challenges is vital to maintaining effective reentry initiatives that reduce recidivism and foster community reintegration.