This article reports on a descriptive study of youth identity as developing through "trajectories of identification" in a science outreach apprenticeship program designed to transition urban African American youth to professional work and career aspirations. A sociocultural framework of identity development is utilized, incorporating the notions of prolepsis, negotiated identity positioning, taking on roles of agency and purpose, and working in a borderland that hybridizes culture. Interpretive case studies focusing on such trajectories of identification were conducted in a program combining an out-of-school science and engineering learning environment with an outreach workplace for high school aged youth. The cases show the promise and pitfalls of the program's attempts to position the youth along positive trajectories. (Contains 1 note.)