Students in the secondary education pipeline, the 6-year period between 7th and 12th grades, deal with external and internal conditions that facilitate or hinder progress to graduation and beyond--these conditions offer resilience or resistance and influence student movement through public schools. This study follows an urban middle school cohort from 7th grade through the senior year of high school. Key events, structures, and relationships supported the development of resilience and resistance during this time and revealed multiple paths to graduation. Examining this longitudinal data set helps to identify and understand urban student issues that, in some cases, were present from the beginning of the secondary experience. This work also helps us draw inferences about the complex context of urban high school communities that promote and inhibit student success. Data in this study indicate that students started on a trajectory toward dropping out long before 12th grade. Students made choices and exhibited characteristics in 7th, 8th, and 9th grade that played out as they exited the educational pipeline prior to graduation. The study documents that negative student choices can be overcome through strong interventions that deal with attendance, discipline referrals, teacher expectations, and multiple options for "catching up" when a student lags in the credit requirement for graduation. (Contains 7 tables and 2 figures.)