Children of families involved with child welfare services are considered high-risk and are vulnerable to developing problems in a number of domains. In particular, educational achievement among this population tends to be lower relative to general population peers. The goal of this qualitative study was to understand the educational aspirations and subsequent pathways of young adults with former child welfare involvement. Semi-structured interviews were conducted with seven young adults (mean age of 31 years) from Ontario, Canada about their educational aspirations in high school and factors that served as facilitators and obstacles to their achievement. The results indicate youth had high hopes and dreams for their future in high school. However, complex challenges impeded the realization of these dreams. Although all seven participants initiated post-secondary programs, only one reached successful completion. None of the young adults achieved the educational and occupational dreams they had in high school. Nevertheless, returning to school remains a prominent future goal for most participants. Despite significant challenges and unrealized educational aspirations, youth with child welfare experiences continue to place high value on education in inspiring hope and optimism for the future. Addressing barriers to educational achievement for youth with child welfare involvement remains an important focus to help educational aspirations become a reality.