This research applies a qualitative approach to investigate the relationship between Muslim leadership, justice and trust with the police in Queensland, Australia. The research addresses the process and deeper dynamics of Muslim leaders seeking to win legitimacy within their own communities in a climate of counter-terrorism. The research was informed by 29 semi-structured interviews with Muslim community members and 14 police personnel. The findings expose a conundrum where certain behaviours initiated by Muslim leaders to win legitimacy and influence within Muslim communities simultaneously carry the potential to draw the suspicion of police. The ensuing dynamics expose the risk of police not only perceiving Muslim leaders with the greatest legitimacy as the least favourable engagement partners, but Muslim leaders with less legitimacy as more favourable engagement partners. The result is the potential for a strategic dilemma where the ensuing partnership fails to possess the necessary influence to achieve the desired victory over community hearts and minds.