This study investigated how persuasive agents modify their compliance-gaining message strategy selection when they are confronted with noncompliant male and female persuasive targets in a variety of relational contexts. Based on instrumental learning theory, it was hypothesized that persuasive agents in noninterpersonal contexts would respond to noncompliant persuasive targets by increasing their preference for punishment-oriented message strategies and decreasing their preference for reward-oriented message strategies, whereas persuasive agents in interpersonal contexts would increase their preference for reward and punishment-oriented message strategies. Results confirmed the hypothesis. Moreover, males were expected to respond to noncompliant persuasive targets with more punishment-oriented strategies than females, and females were expected to use more rewarding strategies to secure compliance from noncompliant persuasive targets. However, results indicated that females responded to noncompliant persuasive targets with more punishment and reward-oriented strategies than males. Results also showed that the effects of persuasive agents' gender on message selection is mediated by the gender of persuasive targets and the duration of the relational consequences.