Individuals high in social dominance orientation (SDO; Sidanius & Pratto, 1999) endorse group hierarchies and social inequality. Surprisingly little research has addressed contextual factors associated with reduced intergroup biases among such individuals. The present investigation considers a Person × Situation approach to this question in two British prisons, exploring the contextual factors outlined in the Contact Hypothesis (Allport, 1954). White inmates scoring higher in SDO exhibited significantly less in-group bias when reporting increased contact with Black inmates (Studies 1 & 2), when perceiving that favourable contact conditions are institutionally supported (Study 1), or when experiencing more pleasant personal interactions with Black inmates (Study 2). These SDO × Contact Condition moderation effects were mediated in Study 2: among high-SDO individuals, increased empathy towards Black inmates mediated the relation between contact variables and lower in-group bias. Implications for considering individual differences and empathy in contact settings are considered.