Longitudinal growth trajectories of reading and math achievement were studied in four primary school grade cohorts (GCs) of a large urban district to examine academic risk and resilience in homeless and highly mobile (H/HM) students. Initial achievement was assessed when student cohorts were in the second, third, fourth, and fifth grades, and again 12 and 18 months later. Achievement trajectories of H/HM students were compared to low-income but nonmobile students and all other tested students in the district, controlling for four well-established covariates of achievement: sex, ethnicity, attendance, and English language skills. Both disadvantaged groups showed markedly lower initial achievement than their more advantaged peers, and H/HM students manifested the greatest risk, consistent with an expected risk gradient. Moreover, in some GCs, both disadvantaged groups showed slower growth than their relatively advantaged peers. Closer examination of H/HM student trajectories in relation to national test norms revealed striking variability, including cases of academic resilience as well as problems. H/HM students may represent a major component of “achievement gaps” in urban districts, but these students also constitute a heterogeneous group of children likely to have markedly diverse educational needs. Efforts to close gaps or enhance achievement in H/HM children require more differentiated knowledge of vulnerability and protective processes that may shape individual development and achievement.