According to Carnegie Commission's Report (1992), 40 percent of adolescents' non-school hours are unstructured and unsupervised. After-school hours have been reported as the most risky time for children to get involved in juvenile crime or to become the victims of violent crime. Consequently, there has been increased effort to serve the needs of children through well-organized after-school programs. The recent youth development literature supports that after-school programs should focus on specific skills and values that can be transferred to participants' life outside the program (Hellison, 2003). Although the transfer of skills and values learned in the program to other contexts has been a critical aspect of program implementation, the topic has not been widely explored. The purpose of this study was to investigate after-school program participants' perceived barriers to transferring Personal-Social Responsibility (Hellison, 2003) goals to their classroom settings. Based on Erickson's (1993) concept of cultural boundaries and borders, this study focused on exploration of specific cultural differences that hinders transfer of program values to classroom settings. This study was investigated through a qualitative case study that included observations and interviews. Five participants (3 fourth graders, 2 fifth graders) were selected based on the length of participation and attendance rate. Interview transcripts and fieldnotes were inductively analyzed in order to find emerging themes and categories (Miles & Huberman, 1994). The trustworthiness of data was ensured by data source triangulation, peer debriefing, and member check interviews (Lincoln & Guba, 1985). After-school program participants' ability to transfer program goals to their classrooms was impeded by two types of borders: (a) structural borders and (b) psycho-social borders. Structural borders were caused by the differences in expectations between after-school program and classrooms. The pressure of standardized testing, individualistic class organization, the strong emphasis on order and control in their classrooms were contradicted to empowerment-based program culture. Psycho-social borders were formed by the differences in perceived atmosphere between after-school program and classrooms. Compared with positive characterizations of after-school program (e.g., having fun, feeling safe, building relationships), participants' perceived classroom culture was characterized by a sense of frustration, boredom, feeling unsafe, and feeling anger and frustration. The discrepancy in perceived atmosphere between two settings impeded participants' ability to apply the program goals to their classrooms. The findings of this study can suggest specific strategies that can bridge the cultural gaps between after-school program and classrooms in order to facilitate transfer of after-school program goals.