Adaptive behaviour requires animals to select appropriate learning strategies. In my talk, I will present complementary studies in humans and mice that address this question across behavioural and circuit levels. Using EEG recordings during tactile learning, I will show that humans adopt distinct adaptive strategies, supported by frontal-cingulate and frontal-sensory cortical networks. I will then describe how longitudinal two-photon calcium imaging, causal circuit manipulations, and computational modelling in mice reveal the cellular mechanisms underlying contextual learning, demonstrating that orbitofrontal feedback signals reconfigure sensory cortical representations to support cognitive strategies necessary for flexible behaviour. Together, these findings provide a unified framework linking individual differences in adaptive learning with the cortical circuits that implement flexible behaviour across species.