The only Hebrew picaresque maqāma from Yemen, Sefer hamusar captivates its readers with trickster tales of wandering and adventure while offering moral guidance and a spiritual ascent via kabbalistic study. In Beguiling Guidance, Adena Tanenbaum explores these tensions, along with the literary, social-historical, philosophical, and kabbalistic aspects of Sefer hamusar, and situates the work in its broader 16th-century framework. Applying a fresh reading, she analyzes Alḍāhirī’s maqāma as a rich repository of intellectual history; treats his travel narratives as composites of fiction and fact; and uncovers the cultural assumptions and self-definitions underlying his representations of Muslims, which she shows to be far more variegated and nuanced than previously acknowledged. Beguiling Guidance should appeal to readers interested in transregional cultural exchange and the diffusion of texts; pre-modern fiction and travel writing; and Muslim-Jewish power relations in the late medieval/early modern Middle East. It also serves as an introduction to the vibrant culture of a Jewish community that traced its presence in South Arabia back to antiquity.