Judean hagiographies are unusual. Some are unexpectedly structured: a saint’s life in the form of a history text. Others offer surprising content. Expected hagiographic stylizations, for example, often depict moments in which the saint is offered money for a miracle. In such cases the saint invariably refuses. Judean saints, however, accept gratitude willingly – often with cash amounts recorded. The peculiarities of these works have regularly been examined on literary and theological grounds. In this dissertation I propose a different approach: socio-economic context. The monasteries that produced these texts were utterly dominated by the environment of Christian Jerusalem. Although often commented upon, the unmined implications of this reality hold the key to understanding these hagiographies. It is only by examining these monasteries’ ties to – and embeddedness within – their peculiar context that we can perceive the mindset that produced such baffling texts. Lengthy historical, literary, and archaeological analysis force Judean hagiography to give up its secrets. These works were in fact not odd at all. Rather, they were hyper-specialized, a unique adaptation to a unique environment. True, we do not see their like in other eastern regions over the span of late antiquity. Yet this is to be expected. Nowhere else can we find the particular conditions that brought these works into being. Nor can we understand the Judean works absent their milieu. It is only upon the foundation of layers of context that these hagiographies stand high enough to view. They were, most accurately, Holy Land hagiographies: a label as unique as the land that produced them.