The paper explores India's response in the face of the COVID-19 educational crisis compared to the educational thoughts and experiments of Rabindranath Tagore, Asia's first Nobel laureate and an avid educator. The context of the study is formulated from the perception that the past and present are interconnected; hence examining similarities and dissimilarities between them can reveal latent undercurrents. A comparative historical method is employed for the study to take three diverse yet interconnected periods in the Indian education system--the Tagorean/colonial period, the post-independence period, and the pandemic period--for a continuous and comprehensive evaluation. Tagore's educational experiences evidenced that the colonial system reeled under biases that alienated the natives from their nation and its operations. Despite the efforts, the post-independence period bears remnants of the colonial system. The educational response to the pandemic also exhibits specific social, cultural, and economic tensions similar to its predecessors. As the COVID-19 lockdown implementation has forced shutters on the educational institutions, an increasing emphasis is laid on digital education without adequate engagement with the pre-existing challenges. Under this convoluted circumstance, the paper opines that colonization continues to be the underlying process propelling the education system. Thus, the Tagorean ideals of education and its indigenous ways require urgent consideration before falling back on the old system post pandemic or endorsing digital education as the next giant stride in education.