In this historically and politically grounded article, I situate the deployment of the concept of keid (or cunning) in Moroccan literature and cinema within the larger struggle for gender equity during the late twentieth century. This chapter examines two key players through their “Wiles of Women” texts: writer and sociologist Fatima Mernissi's trilingual Qui l’emporte la femme ou l’homme? and filmmaker and screenwriter Farida Benlyazid's Les Ruses des Femmes. The first part considers keid within the contexts of the Qur’an and Arab history and literature through figures such as 'Aicha, Scheherazade and Kahina, as well as keid's resonance with related concepts fitna (chaos) and hchouma (shame) within the Maghreb. The second part considers contemporary Moroccan interpretations and receptions of Mernissi's story and Benlyazid's film, which typically see them as celebrations of women's empowerment or reifications of their oppression. I suggest that their meaning is neither fixed at nor between the two poles of empowerment or patriarchy but remains fluid and malleable, as Mernissi and Benlyazid engage in readings of foundational religious texts and work within their own traditions (historical, cultural, and religious) in order to unearth models of powerful female figures from their real or mythological past.