Studies document degradation and loss of publicly owned urban woodland area following adjacent residential development due to residential encroachment. Residential encroachment is the negative impacts of housing land uses within both rural and urban green infrastructure networks. Prevailing planning, design and management approaches in Southern Ontario municipalities in Canada indicate planning and management tools have been developed to remove and impede encroachment impacts; however, many are infrequently implemented. This lack of implementation contributes to a high prevalence and spatial area of encroachment within Southern Ontario municipal woodland edges with adjacent housing. Long interviews were conducted with the planners, landscape architects, woodland managers and bylaw enforcement staff of six Southern Ontario municipalities to determine the barriers to implementation of municipal encroachment tools. Results indicate key barriers to policy implementation that reflect a lack of awareness of, and priority placed on addressing, residential encroachment impacts, and impacts following the point of development in general. Barriers include: (1) insufficient community and municipal access to information regarding residential encroachment and their significance relative to other development impacts; (2) lack of clarity of goals by municipalities and between departments; (3) insufficient municipal leadership and commitment to limiting encroachment; (4) lack of sufficient means within municipal departments to prevent and address encroachment; and (5) ineffectual dynamics of enforcement. Recommendations for overcoming barriers to the development and implementation of effective approaches for addressing encroachment are provided.