The impact of the pandemic varies from one country to the next, but poor and developing countries are the ones that are most at risk. This risk is compounded when it concerns sectors that are more vulnerable than others. Such is the case of the Philippine education sector. In this essay, we will look into the experiences of the Philippine education sector amidst the COVID-19 onslaught. We will glean insights that can serve as lessons that point to ways we can improve from such experiences. We will discuss how the prevalent issues of inequality, poverty, and reactionary politics have forced Filipino families, especially students, into a position where they are expected to continue pursuing quality education despite the pandemic taking its toll on the economic resources and mental health of families, students, and teachers. We will try to show what steps can be taken for the Philippine education sector to become more prepared, resilient, and effective in crisis contexts.