The madness of the knight Orlando, driven by unrequited love, sets into motion a sprawling conflict that intertwines the fates of Christian and Saracen warriors. The protagonist, Orlando, seeks to reconcile his duty to Charlemagne with his obsessive pursuit of Angelica, a quest that forces him to navigate a world governed by magic, capricious fate, and shifting alliances. Opposing him are the logistical demands of a massive war, the interference of supernatural entities, and his own psychological unraveling. The narrative framework employs a complex, non-linear structure, utilizing frequent digressions and multiple intersecting plot threads that mirror the chaotic nature of the chivalric code.

Readers and critics frequently highlight the work's immense influence on subsequent Western literature, particularly its role in shaping the modern fantasy genre. Discussion often centers on the balance between the poem's lighthearted, ironic tone and its underlying critique of the rigid chivalric social order. Scholars emphasize the effectiveness of Ariosto's world-building, noting how the atmosphere shifts seamlessly from high-stakes warfare to whimsical, dreamlike encounters. Many readers appreciate the intricate plotting, though some note that the sheer volume of characters and subplots requires careful attention to follow. The text remains a subject of study for its innovative narrative techniques and its enduring commentary on the human condition.