Supervisory mentoring represents a type of social dilemma called a delayed social fence. This study adopts a social dilemma perspective to examine how the three types of psychological contracts (balanced, relational, and transactional) perceived by supervisors differently influence their mentoring. Drawn on social dilemma perspective, we proposed that supervisory mentoring would be more likely to occur when supervisors perceived benefit return from their mentoring provision in a timely manner. The results obtained from a sample of 596 supervisor–subordinate matched data from the self-reported questionnaires completed by 225 sales agent teams in the insurance industry in Taiwan support our predictions. Consistent with the social dilemma perspective, supervisory mentoring is more likely among subordinates whose supervisors perceived balanced psychological contract, while supervisory mentoring is less likely among subordinates whose supervisors perceived transactional psychological contract. Furthermore, we found that supervisory mentoring is positively related to subordinate performance. Our mentor-centric multilevel framework helps identify the social dilemma nature underlying mentoring provision, and verify the positive influence of mentoring on protégé performance.