By the thirteenth century, tears were a ubiquitous feature of accounts of saints’ lives. Despite the widespread acceptance of tears as an expression of holiness, they could, however, present a special challenge for interpretation and female tears were often the subject of doubt. Divinely bestowed tears might be subject to criticism and uncertainty over whether they could be read as an authentic sign of devotion and the presence of God. This essay argues that doubt over the sincerity of tears was a topos in the narrative of saintly struggle – something a saint must endure as a test of faith and sanctity – and was a corollary to achieving certainty in thirteenth-century female saints’ lives. As the century came to a close, however, tears began to be more openly questioned. The essay assesses the evolving doubt surrounding lachrymose expressions of devotion in the fourteenth century and accounts for changing attitudes by drawing on both saints’ lives and theological sources. It is argued that this doubt was a reflection of broader changes in the acceptance of physical and emotional expressions of sanctity and was part of the ‘gradual criminalization’ of the female body in the fourteenth century.