We are often faced with the need to abandon no-longer beneficial rules and adopt new ones. This process, known as cognitive set reconfiguration, is a hallmark of executive control. Although cognitive functions like reconfiguration are most often associated with dorsal prefrontal structures, recent evidence suggests that the orbitofrontal cortex (OFC) may play an important role as well. We recorded activity of OFC neurons while rhesus macaques performed a version of the Wisconsin Card Sorting Task that involved a trial-and-error stage. OFC neurons demonstrated two types of switch-related activity, an early (switch-away) signal and a late (switch-to) signal, when the new task set was established. We also found a pattern of match modulation: a significant change in activity for the stimulus that matched the current rule (and would therefore be selected). These results extend our understanding of the executive functions of the OFC. They also allow us to directly compare OFC with complementary datasets we previously collected in ventral (VS) and dorsal (DS) striatum. Although both effects are observed in all three areas, the timing of responses aligns OFC more closely with DS than with VS.