One important response to COVID-19 was the intensification of the use of digital media to deliver education. However, the results are paradoxical, since the digital revolution did not lead to improvement of the social quality of teachers’ working circumstances. We analyze “internal” or subjective oriented constitutional and “external” or objective orientated conditional factors related to teachers that determine the adaptation of digitalization, taking a social quality perspective. Through a case study in the most advanced educational hub of India—Delhi—we find that the digital revolution helped India to address the first-order problems in digital transformation, namely concerning objective infrastructural facilities. The second-order problems, particularly changing the subjective belief structures of teachers related to the integration of technologies, appear to remain a challenge. As India has recently adopted a new education policy (2020), the findings of our study have significant relevance to improving the accessibility and utilization of digital technology in educational spaces.