Event-related brain potentials (ERPs) have revealed multiple mechanisms by which contextual constraints impact language processing. At the same time, little work has examined the trial-to-trial dynamics of context use in the brain. In the current study, we probed intraindividual variability in behavioral and neural indices of context processing during reading. In a concurrent self-paced reading and ERP paradigm, participants read sentences that were either strongly or weakly constraining completed with an expected or unexpected target word. Our findings revealed substantial within-subject variability in behavioral and neural responses to contextual constraints. First, context-based amplitude reductions of the N400, a component linked to semantic memory access, were largest among trials eliciting the slowest RTs. Second, the RT distribution of unexpected words in strongly constraining contexts was positively skewed, reflecting an increased proportion of very slow RTs to trials that violated semantic predictions. Among those prediction-violating trials eliciting faster RTs, a late sustained anterior positivity was observed. However, among trials producing the differentially slowed RTs to prediction violations, we observed a markedly earlier effect of constraint in the form of an anterior N2, a component linked to conflict resolution and the cognitive control of behavior. The current study provides the first neurophysiological evidence for the direct role of cognitive control functions in the volitional control of reading. Collectively, our findings suggest that context use varies substantially within individual participants and that coregistering behavioral and neural indices of online sentence processing offers a window into these single-item dynamics.