Disaster management agencies should be exemplars of learning given the volatility of their operating environment. However, there are cognitive, social, and organizational barriers that prevent these organizations from learning. The purpose of this article is to use the Caribbean Disaster and Emergency Management Agency (CDEMA) as an example of an organization that achieves double-loop learning in spite of known barriers. This research shows significant learning variations in the CDEMA organization from the regional to the national level. The results demonstrate that the CDEMA Coordinating Unit and a few national member agencies achieve double-loop learning, while the opposite is true for many national disaster offices. Analysis of this variation is one contribution to the disaster management and organizational learning literature. The article also suggests that organizational culture is an important precursor to learning and adds a much needed case example to the management and learning literature. The study ends with a proposal for future research in the area of disaster management, culture and learning, and propositions for national disaster offices to consider in order to enhance double-loop learning.