While high school attrition is a critical issue in the ongoing effort to reduce disparities in educational equity across race and class, rhetoric on the “high school dropout crisis” frequently overlooks the large number of students who reenroll in school or earn their credentials in alternative schools or GED programs. The number of youth and young adults who have returned to school in alternative education settings is growing, but we know little about these students and why they persist. This year-long study explored the experiences, expectations, and identities of nine adolescents who returned to school in a community college-based program for urban high school dropouts. Building on a tradition of ethnographic research with high school leavers (e.g., Fine, 1991; Luttrell, 1997; Rymes, 2001) and using a critical-constructivist approach, I grounded this study in a conceptual framework developed around three strands of work: post-structuralist narrative, identity and possible selves, and youth literacies. Data sources include interviews, conversation groups, observations, and document analysis. This research offers insights into how students are positioned by assumptions and dominant narratives about urban high school students and dropouts. Via their out-of-school writing practices, their talk about experiences in the program, their narratives about high school, and their hopes and expectations for the future, participants revealed their understandings of success and failure and the ways in which they enacted and resisted identities as “dropout” and “college student.” In particular, this study documents how students negotiated the positions made available to them within the program’s discourse. I critically investigate how and to what extent educators welcome students back to school, and what components of returning students’ experiences, identities and “cultural repertoires of practice” (Lee, 2007) are valued. The stories of participants in this study offer new perspectives on high school attrition and persistence, suggest a number of opportunities and challenges associated with critical pedagogy, and confirm the importance of capitalizing on students’ out-of-school literacy practices. This study examines possibilities for reimagining returning students’ expansive social networks, past experiences, and home cultural practices as resources rather than risk factors.