This chapter discusses two Middle English Charlemagne romances, The Siege of Milan and The Sultan of Babylon, to illuminate post-1291 anxieties about royal politics, Christian infighting, and God’s will and support. It brings these romances into conversation with two main bodies of literary and historical material. The first consists of writings that polemically engage with the question of whether English and French kings should prioritize domestic affairs or crusading activity. The second consists of poems, letters, and chronicles that, written by Christians following crusading defeats, feature wrathful rebukes of God and threats of conversion to Islam. I draw on this latter corpus to offer a new interpretation of the literary motif of the “afflicted Muslim” who vents his military frustration on his “gods,” arguing that such depictions should be understood as projections of Latin Christian anxieties about God’s lack of support to the crusading enterprise.