The brain is capable of creating predictive models of the environment by internalizing statistical regularities in sensory inputs, allowing individuals to perceive and react to the world. However, these predictions must be updated as context changes. While previous research has often ignored this issue, it is unclear whether contextual revisions apply selectively to relevant expectations for adaptive behavior. In this fMRI study, we investigated how contextual visual expectations spread through the cortical hierarchy as beliefs are updated. Participants were trained to learn contextual sequences in a volatile environment where two alternating contexts contained different sequences of object images. The experiment tested for the emergence of contextual expectation suppression in two tasks, with task-relevant and task-irrelevant expectations. The results showed that contextual expectation suppression emerged progressively across the cortical hierarchy as participants attuned themselves to the context. Expectation suppression appeared first in the insula, inferior frontal gyrus, and posterior parietal cortex, followed by the ventral visual stream and early visual cortex. This selective suppression applied only to task-relevant expectations. These findings suggest that an insular and frontoparietal executive control network may guide the flexible deployment of contextual sensory expectations for adaptive behavior in our complex and dynamic world.