This study re-evaluates the way free will is portrayed in Anglo-Saxon poetry, and shows that Anglo-Saxon vernacular poetry, both religious and secular, was as capable of grappling with fundamental theological and philosophical questions as homiletic writing and theological treatises. It also shows that free will was prominent among the theological and philosophical issues investigated in Anglo-Saxon poems from a number of different manuscripts. In order to fully understand the range of teachings about free will that were available in Anglo-Saxon England, we must understand what the poetry—not just the more theologically authoritative prose—says about free will. In Anglo-Saxon literature the concept of free will is particularly complicated by both a Christian tradition carried over from the continent as well as a cultural Germanic tradition. Germanic ideas of fate and Boethian ideas of providence were both extremely influential in Anglo-Saxon poetry, but poems such as the biblical versification Genesis B also show evidence of the influence of late antique patristic writers like St. Augustine of Hippo. Often complex ideas about free will influenced not only biblical versifications, as might be expected, but even ostensibly secular, heroic works such as Beowulf. Yet rather than just borrow ideas about free will, fate, providence, and grace from both Germanic sources and Christian sources, Old English poetry weaves all of these ideas together so thoroughly that at times they stop being distinguishable and become something new. In this way Anglo-Saxon vernacular poetry creates and champions syncretic notions of free will that are uniquely Anglo-Saxon.