Web technology, in its current avatar, has been fiercely debated in terms of its efficacy in the field of humanities pedagogy. However, the verdict has not yet been delivered. This chapter is an attempt to explore the theoretical premises of web technology within which they operate and its interactions with pedagogic forms—its circulation, dissemination, and hybridization; its impact in terms of teaching-learning behavior; the space of internal dynamics of such an interface and the challenges that such interactions throw up; the integration/externalization of digitization within the pedagogic framework; and the possibilities of indigenization, and, by extension, transformation of such technology within the Indian classrooms.