Nature-triggered disasters have been causing havoc in Canada over the past decade. Although many of these hazards cannot be prevented (e.g., earthquakes), their impacts can be managed through judicious planning and by mobilizing national resources. Considering the relentless force of nature and the degree of anticipation and preparedness needed, Canadian civil and military institutions must synergize to optimally utilize human capital, knowledge, and financial resources. Both the Canadian Armed Forces (CAF) and civil society actors have emphasized the importance of enhancing adaptive capacity and reliance on the armed forces for disaster response. As such, frequent involvement in domestic responses diverts the CAF’s focus away from national and international security threats, underscoring a serious national concern. Against this backdrop, the present paper analyzes existing civil-military cooperative models in Disaster Management in Canada and the USA. Three objectives are set: a) to explore the armed forces’ main tenets and approaches to disaster and emergency management, b) to find similarities and differences in institutional and resource priorities (before and during the onset of extreme nature-triggered events), and c) to identify the best collaborative practices and modes of operation of stakeholders involved. Using a case study approach, a desktop review of policy papers and an event database for two large-scale disasters: one in the United States (Hurricane Katrina in 2005) and one in Canada (the 1997 Red River flood in Manitoba) was carried out. The results offered the following major findings: a) organizational and cultural differences between the civil and military authorities in both countries drive the nature of disaster management; b) centralization vs. resource decentralization has remained the key factor in speeding up disaster response; c) political and legal scope and limitations in civil-military cooperation are often blurred; and d) the sole application of the Command, Control, and Communication (C3) approach becomes problematic when a multi-stakeholder approach is preferred for disaster management.