The visual system quickly registers perceptual regularities in the environment and responds to violations in these patterns. Errors of perceptual prediction are associated with electrocortical modulation, including the visual mismatch negativity (vMMN) and P2 event-related potential. One relatively unexplored question is whether these prediction error signals can encode higher-level properties such as surface segmentation, or whether they are limited to lower-level perceptual features. Using a roving standard paradigm, a triangle surface appeared either behind (featuring amodal contours) or in front of (featuring real contours) a second surface with hole-like windows. A surface layout appeared for two to five repetitions before switching to the other "deviant" layout; lighting and orientation of stimuli varied across presentations while remaining isoluminant. Observers responded when they detected a rare "pinched" triangle, which occasionally appeared. Cortical activity-reflected in mismatch responses affecting the P2-N2 and P300 amplitudes-was sensitive to a change in stimulus layout, when surfaces shifted position in depth, following several repetitions. Specifically, layout deviants led to a more negative P2-N2 complex at posterior electrodes, and greater P300 positivity at central sites. Independently of these signals of a deviant surface layout, further modulations of the P2 encoded differences between layouts and detection of the rare target stimulus. Comparison of the effect of preceding layout repetitions on this prediction error signal suggests that it is all or none and not graded with respect to the number of previous repetitions. We show that within the visual domain, unnoticed and task-irrelevant changes in visual surface segmentation leads to observable electrophysiological signals of prediction error that are dissociable from stimulus-specific encoding and lower-level perceptual processing.