The use of the serpent as a symbol of temptation goes back to Genesis. In rabbinic and early monastic texts from late antiquity it symbolizes intrusion, disruption and distraction during prayer. Contemporaneous monastic and rabbinic stories reveal striking resemblances in using imageries of serpents coiled around the foot of the praying man in order to address and conceptualize problems and dangers that occur during prayer. This constitutes a part of a large corpus of intertextual links between the two traditions that point to influences, common themes, and parallel preoccupations. A comparison between the uses of the image of the serpent as intrusion and disruption in monastic and rabbinic texts reveals a common discourse regarding the cognitive state during prayer. While monastic and rabbinic authors share a common question – how to maintain the correct disposition while praying – they formulate it in different manners and to different ends. This brings to light the different ways in which mind’s activities were conceptualized as a link to the divine, and the undefined and complex dynamics of the state of mind in prayer.