Since the implementation of Taiwan’s Social Safety Net policy in 2018, empirical research on social services for vulnerable families remains underdeveloped, particularly from service-user perspectives. In collaboration with a support program in eastern Taiwan, this multiple-case study interviewed six participants from four households raising adolescents to explore the complex adversities they experience and their perceived service outcomes. The findings revealed three primary challenges: pronounced economic pressure, strained family relationships, and psychobehavioral challenges, compounded by the structural constraints of rural employment scarcity and entrenched gender roles. Effective intervention requires holistic needs-based support, sustained support with timely responsiveness, and sufficient resource network. Notably, positive changes were reported in adolescents’ behavior, caregivers’ mental well-being, and family dynamics. However, structural barriers remained largely unaddressed. Encouraging all family members to confront problems together, rather than overburdening a single caregiver, emerged as a pivotal outcome of this family support program.