Munira al-Mahdiyya (c.1885-1965), dubbed the ‘Sultana of Ṭarab’, was one of the most influential and successful Arab female singers of her generation. As a lower-middle class woman with minimal education, she began working in the less reputable rank of the female singing profession as a 'alma, before quickly rising to the top of the Cairene musical performance scene that she would dominate for two decades. Al-Mahdiyya deliberately and frequently subverted gender roles in ways that rendered her a figure of rebellion. This, combined with her vocal support and participation in the 1919 uprising might be more fully understood in the immediate context of her profession, alongside personal, artistic, and other practical considerations. Cultural histories have generally focused their discussions of Al-Mahdiyya’s career on the period in which she was already an established figure of some wealth and renown. This has been due to an emphasis on press accounts, interviews, and promotional material rather than the recordings and performances she produced. As such, scholarship has largely reflected upon the social impact of journalistic representations of her as a controversial celebrity that transgressed gender boundaries of a Muslim Egyptian woman. In this paper I seek to both broaden and complicate discussions of Al-Mahdiyya’s socio-cultural impact through a discussion of the interplay between her personal and professional lives. Whilst it is acknowledged that she helped reconfigure not only the repertory but the social parameters of her profession, questions remain: how did her personal background and career trajectory contribute to this reconfiguration, and how did her identity as an artist — her choices of content, style of delivery, environment and professional demands — help shape it? To answer, I pair a chronological discussion of biographical circumstance in the context of social change with musical and literary analysis of her surviving recordings. In so doing, I hope to render audible Al-Mahidyya’s own navigations of social norms, and particularly those relating to class and gender within her profession. In doing so, I make an argument for a more nuanced approach through reflections on socio-economic circumstance, creative motivations and individual agency.