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The COVID-19 pandemic calls for a change of perspective in the educational landscape, and the literary classroom is revealed to be one of the classes that can quickly adopt this change. Teachers of literature began to curate on their syllabi texts that will signify the global feeling and experience of the pandemic. This transforms the literary classroom into a space that directly connects the experiences of students to this ongoing health crisis. The different literary texts read in classes are portals for students to understand the experience of illness as both historical and sociological phenomena. With these events in class, the pandemic becomes both a learning opportunity and a challenge for teachers and students. This paper examines the function of Philippine literature as contextualized in health and illness while teaching during the pandemic, the role of the literature teachers as active agents during global crises, and the value of literature classes for making sense of the global pandemic. Through pedagogical criticism as the methodology employed in this paper, texts like Manuel E. Arguilla’s “Caps and Lower Case,” Benjamin Bautista’s “A Summer Goodbye,” and other texts that show the rich and valuable role of studying literature about illness and health at the time of COVID-19 are analyzed. The discourses about the figure of teacher are also used to theorize on the role of the literature teacher during the pandemic. Lastly, the construction of a literary classroom during the COVID-19 pandemic is examined using online articles on education contextualized in the pandemic. This paper uses theoretical paradigms such as critical pedagogy and health and medical humanities to strengthen its framework for analyzing the texts. To fully understand lessons from pandemic time teaching, the paper demonstrates a sample practice of teaching health and illness literature through an online application, Perusall.