Technological developments affect almost every line of life, including the lives of santri in pesantren. This study aims to uncover the transformation of santri behavior, orthodoxy and heterodoxy, a result of technological developments in the pesantren world. This study uses a qualitative approach with a type of case study. The results showed that some of the orthodoxy behavior that had existed since long ago was still awake in Islamic boarding schools, such as dressing modestly, proficient at reading yellow books and even understanding its contents, always obeying the pesantren's rules, respecting the older and loving younger ones. However, there are also deviant behaviors (heterodoxy) that arise due to the current development, such as imitation of k-pop culture, lack of ability to read books, violating pesantren rules, bullying, transformation of santri religious authority and the change in primary learning sources of santri. However, there are several behaviors that remain the characteristics of pesantren such as solidarity, independence, ta'dzim towards kiai, and managing their own learning.