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Mentorship and other social and relational support have been vital to poverty alleviation and transformative change. It is crucial to understand the underlying factors in the success of mentoring models and subsequent programs to support them. Thus, we conducted a mixed-methods study consisting of longitudinal surveys of community participants followed by semi-structured interviews with 28 community members, eight mentors, and two coaches participating in a community-based mentorship program. Drawing from community-based participatory research in partnership with a non-profit located in a Midwestern United States (U.S.) city, we unpack how the program supported self-sufficiency and economic mobility among adults experiencing financial hardships. Through an infrastructural lens, we attend to individuals’ infrastructuring work in social support, flexibility, and trust to support a “village” model of community-based mentorship. Our results show how the village model differs from traditional mentorship models that assume dyadic, one-to-one, often didactic, and hierarchical relationships (e.g., expert and protégé, adult and child) and are used primarily in the workplace and educational settings. The village mentorship model advocates for less hierarchical and more balanced relationships in non-institutional settings and flexible communication and technological needs. We discuss new research opportunities and design strategies for rethinking technology-mediated mentorship to support poverty-stricken adults in the U.S.