Enhancing community resilience has increasingly involved national and regional governments adopting a multi-stakeholder approach because of the potential interagency benefits. This has led to questions about how best to involve stakeholder groups in translating community resilience policies into practice. This exploratory study contributes to this discussion by addressing two key areas that are fundamental in the concerted effort to build community resilience to natural hazards: (1) stakeholder understanding of community resilience as a concept; and (2) the difficulties associated with the processes of risk assessment and preparedness that stakeholders face locally in building community resilience. Data were collected through semistructured interviews with 25 practitioners and experts within Scotland’s resilience community, and were analyzed through an inductive approach to thematic analysis. These data show how the interpretation of community resilience differs across stakeholder groups. Analysis of the data reveals challenges around the nature of the risk assessment and its role in shaping risk perception and communication. Significant complications occur in communicating about low probability-high consequence events, perceived territoriality, competing risk prioritizations, and the challenges of managing hazards within a context of limited resources. The implications of these issues for policy and practice are also discussed.