As in other parts of the world, the COVID-19 pandemic in India brought with it an unprecedented change in the fabric and structure of the classroom in Indian schools, with teachers having to shift from in-person teaching to online instruction without prior exposure or training to this new interface of teaching and learning. This study—which was part of a larger paper on the newly introduced Arts-Integrated Learning (AIL) approach to teaching in a section of Indian schools—throws light on the perils and the possibilities of online instruction as experienced by teachers and students in two Indian schools. Drawing on the voices of the participants from semi-structured interviews that were conducted over a duration of two months, the study reveals the challenges posed to teachers and students by voluntary and involuntary disengagement, deeply embedded systemic pressures such as shortage of time, technological shortcomings, and teacher-centric pedagogical styles. The study further revealed the changing role and function of the teacher in the classroom, from a source of knowledge to a facilitative agent in the learning process. Additionally, both teachers and students highlighted the benefits of online instruction, citing time saved as an important factor. Given these perspectives from the two most significant stakeholders in the educational landscape, the study offers practical recommendations that could potentially mitigate the challenges posed by online instruction and reimagine the online interface as a tool that could aid both teachers and students in their interactions.