The magnitude of the COVID-19 pandemic challenged societies around our globalized world. To contain the spread of the virus, unprecedented and drastic measures and policies were put in place by governments to manage an exceptional health care situation while maintaining other essential services. The responses of many governments showed a lack of preparedness to face this systemic and global health crisis. Drawing on field observations and available data on the first wave of the pandemic (mid-March to mid-May 2020) in Quebec (Canada), this article reviewed and discussed the successes and failures that characterized the management of COVID-19 in this province. Using the framework of Palagyi et al. on system preparedness toward emerging infectious diseases, we described and analyzed in a chronologically and narratively way: (1) how surveillance was structured; (2) how workforce issues were managed; (3) what infrastructures and medical supplies were made available; (4) what communication mechanisms were put in place; (5) what form of governance emerged; and (6) whether trust was established and maintained throughout the crisis. Our findings and observations stress that resilience and ability to adequately respond to a systemic and global crisis depend upon preexisting system-level characteristics and capacities at both the provincial and federal governance levels. By providing recommendations for policy and practice from a learning health system perspective, this paper contributes to the groundwork required for interdisciplinary research and genuine policy discussions to help health systems better prepare for future pandemics.