Winnipeg’s built heritage is suffering from demolition by neglect, the lack of maintenance on designated heritage buildings which results in their demolition, often in the name of public safety. Although built heritage is a valuable community asset and the issue of demolition by neglect has been discussed for over two decades, little research has taken place to find solutions. This thesis explores the methods used for addressing demolition by neglect in Hamilton, Ontario; Ottawa, Ontario, and Edmonton, Alberta and seeks to understand if these methods would be effective in addressing the issue in Winnipeg, Manitoba. A document analysis and semi-structured interviews were used to uncover the methods for addressing demolition by neglect in the three cities while a focus group considered the applicability of the methods to Winnipeg. The result was a typology of strategies suggesting three recommendations for addressing demolition by neglect in Winnipeg, effective communication, supporting redevelopment and increased political will. When addressing a wicked problem like demolition by neglect, planners, policy makers, researchers and community groups need to take a customised, flexible approach that evaluates the individual context of each heritage building and work together to find solutions that will not only stop the neglect but support a vibrant and sustainable community.