On March 11, 2020, the World Health Organization declared the emerging COVID-19 threat a pandemic following the global spread of the virus. A year later, a number of governments are being handed the concluding reports of national public inquiries tasked with investigating responses, mishaps, and identifying lessons for the future. The present article aims to identify a set of learning obstacles that may hinder effective lessons drawing from the COVID-19 pandemic responses. The seven obstacles discussed in this article are: (1) retaining lessons and implementing them effectively, (2) effectively drawing lessons from other countries, (3) the potential for reforms to introduce unanticipated vulnerabilities elsewhere in the system, (4) political pressure, (5) drawing the conclusions from observations, (6) experts versus decision makers, and (7) reforms may not be related to the actual crisis. Exploring these obstacles will be central to future discussions concerning which kinds of responses will set precedent for future pandemics and global health crises.