On any given day, around 400,000 youths involved in the child welfare system eventually prepare for the transition into safe and stable permanency placements. Although schools play an integral role in permanency planning and transition success, there are no evidence-based programs that focus solely on supporting and improving student educational outcomes. The purpose of this study was to conduct a pilot study of a newly developed education focused transition program, Fostering Educational Success (FES), to examine implementation, dosage, caseload size, acceptability, social validity, and program measurement. Fifteen out of 20 (75%) families completed the full 6 months of FES programming. On average, families received 3.02 direct and .89 indirect service hr per week. Family coaches reported the highest percentage of time spent in program implementation on FES related tasks (31%) such as collaboration, records gathering, family service and discharge planning, etc. Of those who completed the post-program survey, caregivers (n = 13) and youths (n = 9) reported high levels of satisfaction across core program components and support. Acceptability data were mixed with 76.9% of caregivers reported that they would be very likely to recommend the program to others and varying opinions on how long they felt services should be offered. Findings, implications, and limitations are discussed.