Background/Context: In this article, we explore school connectedness for students in a high-poverty urban school. Current approaches to measuring connection conflate behavior and attitudinal measures of connection and rarely explore school connection in urban school settings. Purpose/Objective/Research Question/Focus of Study: We examine interpersonal (attitudinal) and institutional (behavioral) connection in the context of an urban high school. We ask, How are affective and behavioral dimensions of school connection related to one another for African American students in a high-poverty urban high school? How does affective and behavioral connection and disconnection play out in the school lives of students? And how is it related to the specifics of the school context? Research Design: We surveyed 120 high school students and collected observational and interview data on a subset of 20 case study students at an urban high school. Surveys, observations, and interviews focused on capturing students' interpersonal and institutional connection as well as students' academic achievement and academic identities. Findings: Data indicate that in this urban school context, dual dimensions of connectedness (interpersonal connection and institutional connection) operated in different ways for students. Specifically, we describe four connectedness quadrants, highlighting both academic outcomes for students in these quadrants and detailing the ways in which interpersonal and institutional connectedness played out in the context of the school. Students who were connected both interpersonally and institutionally had higher grades and graduation rates. Students who were high on institutional connection but low on interpersonal connection fared next best, and students who were institutionally disconnected were worse off on a variety of outcomes. Students' institutional and interpersonal connection were also deeply tied to aspects of the local school context. Conclusions/Recommendations: These findings raise important concerns with respect to using traditional connectedness measures in urban school contexts and suggest the use of more nuanced measures of connectedness in future studies. Findings also suggest that schools play an important role in structuring experiences of connection or disconnection for students.