A heritage building and its site present a range of challenges when developing preventive conservation strategies for the collection in the building. These challenges originate from the need to preserve the authenticity and physical integrity of the building and site while simultaneously addressing the environmental vulnerabilities of the objects in the collection. To address these challenges, preventive conservation strategies must be specific to each heritage building and the collection in the building, rather than based on a set of prescriptive rules. With heritage buildings, preventive conservation of the collections must balance environmental vulnerabilities of the collections with the available causative factors presented by the context, the ability of the building envelope and its systems to mediate these causative factors, and the capacity of the institution for sustained implementation of the preventive strategy. The authors present an approach to the resolution of these competing or conflicting challenges. This approach engages the preventive conservator, the building specialist, and the responsible institutional steward in a collaborative effort, informed by a systemic understanding of the issues, in developing a realistic and achievable preventive conservation strategy.