This chapter is set in the context of two developing countries, Mongolia and Chile, where digital technology is seen as a powerful icon of the knowledge economy. The predominant and common discourses surrounding the uses of digital technologies in education in these developing countries usually assume rather celebratory stances of the roles digital technologies may perform in education in the digital age. Thus, the research reported here explores the realities, opportunities, and challenges that academic staff face when using digital technologies through the perspectives offered by the field of digital literacy studies. The findings illustrate the close and complex relationships between sociocultural contexts, beliefs, values, and digital literacy practices. The study suggests that more attention needs to be paid to the wider contexts affecting the digital practices around teaching and learning rather than to technologies per se.