The neuropeptide oxytocin plays an important role in mother–infant bonding. However, recent studies indicate that the effects of oxytocin on prosociality are dependent on perceived social context. Using functional magnetic resonance imaging, we examined differential effects of intranasally administered oxytocin on neural responding to 500 and 700 Hz crying that was indicated as emanating from a sick infant and 500 and 700 Hz crying emanating from a bored infant. We found that oxytocin significantly increased insula and inferior frontal gyrus responding to sick infant crying, but decreased activation in these brain regions during exposure to crying of an infant that was labeled as bored. In addition, oxytocin decreased amygdala responding to 500 Hz crying, but increased amygdala responding to 700 Hz crying. These findings indicate that labeling the same infant crying as ‘sick’ or as ‘bored’ drastically changes neural activity in response to intranasal oxytocin administration. Oxytocin increases empathic reactions to sick infants' crying, but lowers the perceived urgency of crying of an infant perceived as bored, thus flexibly adapting adult responses to infant crying labeled in various ways.