The objective of this study is to explore whether social learning has occurred in Yorkton following the flood events that the City experienced in 2010, 2014 and 2016. The study also aims to understand the factors that impacted social learning’s occurrence, its interrelation with the window of opportunity, and the outcomes that it produced. The data for this study came from 15 semi-structured interviews and 110 newspaper articles on the flood events and the infrastructure upgrades. The data showed that the flood experience and the interactions and communications between the City, the Council and the public have produced social learning. However, this learning has been mainly single-loop learning, with some indicators exhibiting double loop learning. While the data revealed no explicit barriers to social learning, the perception that the public cannot contribute to stormwater management issues may have inhibited the degree of social learning that was achieved in Yorkton. In addition, the 2010 flood opened a window of opportunity for change, allowing the City and the Council to introduce a number of expensive upgrades. The subsequent floods contributed to keeping the window open. Furthermore, the data showed that social learning and the window of opportunity are interrelated. As a result of social learning and the policy window that opened after the flood, Yorkton is now more prepared to deal with future events, both in terms of prevention as well as emergency response. However, it was found that social learning is diminishing as a result of the passage of time and the false sense of safety that the infrastructure upgrades created. The diminishing of social learning has policy implications for Yorkton as the city has not yet implemented all the proposed upgrades.