Cultural capital is largely conceptualized as high-status (or “dominant”) knowledge and practices that yield a return or benefit for those who enact these forms of capital. Literature in this field has produced a rich understanding of how cultural capital is transferred from one generation to the next, yet there is little understanding of the micro-interactions in which gatekeepers recognize and acknowledge these forms of cultural capital. This dissertation project aims to deepen our understanding of cultural capital through an investigation of the micro-interactional moments in which gatekeepers “read” adolescent cultural capital “bids”. Situated in the context of the educational experiences of adolescents in a juvenile rehabilitation center, this project provides insight into the cultural repertoires of adolescents who are marginalized by class, conceptions of delinquency, race, and gender. Data for the analysis of these cultural “bids” and readings comes from 20 months of ethnographic methods and interviews of 28 adolescents in a juvenile detention facility. Through this ethnographic examination of bids for the recognition and acknowledgement of literacy practices and non-cognitive skills, I find that adolescents make complex cultural bids that largely align with their social needs and dominant educational values. Whether these bids are acknowledged as dominant cultural capital or relegated to non-dominant capital is influenced by timing, alignment of skills with teacher’s academic framework, and the gatekeepers’ prior perceptions of adolescent behaviors. In an analysis of transitional planning that is essential to successful re-entry for these adolescents, I analyze whether successful cultural bids yield results for these adolescents. I find that adolescents who are able to make successful bids at having their cultural capital read, receive support that contributes to confidence in transitioning from the juvenile detention facility, while adolescents who do not make cultural bids —or who make unsuccessful bids—experience little additional support, resulting in precarious transitions. The findings from this study highlight the importance of the interactional nature of readings of cultural capital, carrying implications for how we can more accurately assess the cultural repertoires of adolescents on the margins of society.