During the late fourth and first half of the fifth century, the Syrian monasticism experienced a radical transformation that made it lose almost its entire specific identity, in comparison with the Egyptian and Palestinian ones. Many specialists on the history of asceticism in the Syrian Orient, in the early Christian period, have often highlighted what they call its encratic features. They cite the harsh and seemingly bizarre forms of ascetic life that flourished in the Syrian region and which raised some eyebrows among the fourth century contemporaries, high valued monastic figures, who seriously questioned the zeal and practices of the Syrian monks, although as we will see, this is not quite an exact and appropriate term to use for the fourth century ascetics within the Syrian space. The most common misconception appears when, by reading about the famous fifth century coenobitic monasteries within the Syrian region, we imagine that the state of affairs was the same a century earlier too. But the things could not have been more different and this study wishes to analyze these specific characteristics of the Syrian monasticism in the fourth century and to show that it was a completely different picture, in contrast with its counterparts in Egypt and Palestine. In doing this, we chose to present two of its most defining concepts: “ihidāyē” and “bnay qyama”.