Despite efforts to do so, environmental sustainability remains elusive, and there is an imbalance between urban growth, biodiversity, and the systems that support all life. This is an ongoing problem for cities and regions, particularly as we face uncertain climate futures. Our communities and the biodiversity that share our lands, water, and skies are increasingly vulnerable to extreme temperatures, intensifying wildfires, storms, and flooding. This lecture explores strategic planning's contribution to the dilemma by investigating the provision of housing and the consequences for ecological values. Using a case study in southwest Sydney, Australia, and noting that the lands were identified for development in the 1970s, approval was given for 1700 residential lots and community facilities on and near significant ecological values. The development assessment process included the national, state, and local governments of Australia due to the significance of some of the species evident, such as the Koala, which is listed as endangered. Some conditions of consent were imposed to protect ecological values. However, there was much criticism surrounding the approval. But, criticism itself is not enough to address this common dilemma. Unfortunately, this case seems to pit housing against environmental sustainability. It suggests that planning enabled "yes" to development and "no" to sustainability. As climate action and the restoration of biodiversity requires immediate address, how can strategic planning and decision-making about development respond differently?