The current educational landscape is undergoing significant transformation due to the integration of technology, which introduces various pedagogical challenges for teachers. This study employed a descriptive qualitative research methodology to provide a comprehensive overview of schools’ and teachers’ digital readiness in classrooms. Data was collected through a survey questionnaire conducted via interviews with teachers followed by quantitative and qualitative data analysis on the responses. The study, conducted across over 60 schools representing various boards in India, identified several key obstacles: a scarcity of grade-appropriate content, scattered digitalization practices, lack of digital content access for teacher preparation, lack of options for assessments and inadequate teacher digital pedagogy skill. Notably, 79% of teachers (n = 77) without integrated content availability expressed that the lack of grade-appropriate content hinders effective digital teaching. In schools with less than 30% digitalization, only 34% of teachers (n = 1148) utilized digital aids, despite having structured timetables. Conversely, in fully digitalized schools, an average of 88% of teachers (n = 460) regularly used digital teaching solutions, benefitting from seamless access. Furthermore, 68% of teachers (n = 78) indicated that the lack of access to digital content for preparation significantly impacts their ability to teach using digital infrastructure. Surprisingly, 62% (n = 92) of teachers expressed that they do not feel sufficiently skilled to use the digital tools and techniques they learned during the pandemic. To fully harness the potential of digital learning, recommendations have been suggested as reflections for school leaders and EdTech solution designers. Acknowledging and addressing these teaching-learning challenges through thoughtful planning and targeted strategies will be key to effectively transform digital education and help achieve the goals outlined in the NEP 2020.