This article sheds light on the educational trajectories of undocumented youth who engage in forms of organizing through a community-school partnership in an urban public school in Chicago. Drawing on data from an ethnographic study in an urban public high school, readers learn that undocumented youth gain a positive sense of identity and belonging to their school and community by participating in a community-based after-school program called The Dream Act Club. First, the article argues that undocumented youth participation in community organizing helps them make sense of their identity in relation to the larger community and societal context. Second, the article argues that social spaces like The Dream Act Club provide networks of support and what Levinson calls (2001) "intimate cultures," enabling undocumented youth to accomplish two things (a) critique and dismantle negative stereotypes around the undocumented status that are perpetuated through the media and political figures on a larger scale, and through school-based personnel perceptions' of undocumented youth on a local, school level; and, (b) critique larger immigration policies through community organizing efforts. By situating these powerful narratives of undocumented youth in the context of current issues in immigration policy, I (they/we) can write against the negative discourses that circulate in the national immigration debate in the United States about undocumented youth. These narratives enable us to consider the voices and needs of undocumented youth through their eyes. Their narratives challenge educators, researchers, and policy-makers to humanize the complicated identity formation processes in contentious political climates to better understand their social worlds and impoverished realities.