Curious as to why conducting gesture are both acknowledged and ignored by choral singers, this article investigates the enigmatic nature of the act of conducting. Education and research are biased toward gestural aspects of the choral conductor role. At the same time, research shows that gestural skills rank strikingly low compared with other musical skills and interpersonal skills. This study endeavors to unpack this enigma, based on 40 interviews with choral singers and conductors in Norway and Sweden. Taking a phenomenological approach, analysis of the fieldwork reveals that singers are more aware of gesture when something out of the ordinary happens, is unclear, or is even particularly appealing. The enigmatic role of gesture is partly due to conceptual ambiguity—gestures are signals that conductors “do” as well as embody the integral conductor “being.” Moreover, four “enigma busting” contextual dimensions were found: complexity of the music, the irreplaceability of gestures in the specific situation, singers’ receptiveness to gestures, and the gestural proficiency of the conductor. The article points at some implications for education as well as future research.