This chapter starts as the Roman Empire fragmented, encompasses the emergence of Christianity and Islam, and explores the donkey’s place in the history of the Middle Ages, as well as what Fernand Braudel termed ‘the triumph of the mule’ in the ensuing early modern period from the fifteenth to the nineteenth centuries. Being closer in time to the present, historical documents are generally richer and more plentiful than for earlier periods, but archaeological excavations and surveys—especially of post-medieval sites and landscapes—are still undeveloped in many regions. Inevitably, therefore, what I present draws as much on textual sources as it does on them. I look first at the symbolic value of donkeys and mules in Christianity and Islam. Next, I consider their disappearance from some parts of Europe in the aftermath of Rome’s collapse and their re-expansion and persistence elsewhere. One aspect of this concerns their continuing contribution to agricultural production, another their consumption as food, a very un-Roman practice. A second theme showing continuities from previous centuries is their significance in facilitating trade and communication over both short and long distances. Tackling this requires inserting donkeys and mules into debates about how far pack animals replaced wheeled forms of transport as Late Antiquity gave way to the Middle Ages. Wide-ranging in time and space, this discussion also provides opportunities for exploring their role in human history in areas beyond those on which I have concentrated thus far. West Africa is one, the Silk Road networks linking China to Central Asia a second, and China’s southward connections into Southeast Asia a third. According to the New Testament Jesus entered Jerusalem on Palm Sunday seated on a donkey (Plate 20). The seventh-century apocryphal Gospel of Pseudo-Matthew also envisages donkeys carrying His mother to Bethlehem, being present at the Nativity, and conveying the Holy Family into temporary exile in Egypt. Donkeys thus framed both ends of Jesus’ life and, given their importance in moving people and goods in first-century Palestine, must have been a familiar sight. But the implications of their place in Christianity’s narrative were originally quite different from those that are generally understood today.