Individuals regularly experience fluctuations in the ability to perform cognitive operations. Although previous research has focused on predicting cognitive flexibility from persistent individual traits, as well as from spontaneous fluctuations in neural activity, the role of learning in shaping preparatory attentional control remains poorly understood. Across 3 experiments, we manipulated the statistical regularities of an attentional orienting paradigm to examine whether individuals modulated attentional flexibility, the readiness to perform a spatial shift of attention, across learned contexts. We found evidence of learning-based modulations in preparatory attentional control settings when the probability of shifting the focus of attention differed based on temporally or color-defined contexts. Furthermore, in the case of color-defined contexts, these modulations in preparatory control persisted even after a change in the underlying statistical properties. Our results indicate that dynamic adjustments in preparatory attentional control are sensitive to the underlying statistical regularities of an environment. This finding has implications for understanding disordered patterns of attentional control and how these patterns might be modified with training.