Measures of teacher–student relationship quality (TSRQ), effortful engagement, and achievement in reading and math were collected once each year for 3 consecutive years, beginning when participants were in 1st grade, for a sample of 671 (53.1% male) academically at-risk children attending 1 of 3 school districts in Texas. In separate latent variable structural equation models, the authors tested the hypothesized model, in which Year 2 effortful engagement mediated the association between Year 1 TSRQ and Year 3 reading and math skills. Conduct engagement was entered as a covariate in these analyses to disentangle the effects of effortful engagement and conduct engagement. Reciprocal effects of effortful engagement on TSRQ and of achievement on effortful engagement were also modeled. Results generally supported the hypothesized model. Year 1 variables had a direct effect on Year 3 variables, above year-to-year stability. Findings suggest that achievement, effortful engagement, and TSRQ form part of a dynamic system of influences in the early grades, such that intervening at any point in this nexus may alter children’s school trajectories.