Paul Bowles was an American expatriate known for his work as a composer, author, and translator. He settled in Tangier, Morocco, in 1947. He published several short stories, three novels centered around Moroccan social and political culture, as well as numerous translations of oral stories, including the work of well-known Moroccan author Mohamed Choukri. Due to his extensive list of Moroccan representations, Bowles curated a legacy as a leading contributor in introducing the Western world to Morocco, which current scholarship upholds without question. This research calls into question Bowles’ qualifications for being a pseudo-ambassador of Moroccan culture and argues instead that he is an unreliable source of information. This position revolves around three factors: Bowles demonstrates a lack of cultural sensitivity necessary for unprejudiced depictions of differing cultures, his perpetually homogenous social circle of Westerners in Morocco, and his self-proclaimed fluency in Morocco’s Arabic dialect darija. Evaluating his refutable qualifications and neglectful contributions to the Western world’s understanding of Moroccan culture exposes the misconception that Bowles is a reliable spokesperson. This research encourages and emphasizes the importance of further scholarship towards a reexamination of Bowles’ work, his impact on the Western canon’s perspective of Morocco, and historiographies created by previous scholars. From a broader perspective, this study contributes to literary Orientalism scholarship and advances critical cross-cultural understanding.