The problem of engaging boys in music is a perennial one. Boys are typically less involved in formal music-making than their female counterparts and tend to achieve lower grades in music at school. Of all the types of musical participation, singing is one that is often shunned by boys because of its association with gender-incongruence: it is not always socially acceptable for boys to sing at school. This research addresses the fact that singing classical or folk music in class is challenging for boys. For educators involved in a sequential, voice-based program, this is a significant concern. The problem is explored through literature from the field. Responses to the problem are also offered through recent research and reference to practical examples.