Local government in Australia is critically positioned to provide built environment initiatives that respond to the increasing prevalence of non-communicable diseases (NCD), climate change, and various other human and ecological health considerations. However, action on the ground has not been as widespread as might be expected, particularly in improving community health. This research explores the barriers to and enablers of the implementation of healthy planning and active living initiatives through in-depth interviews with healthy planning and active living advocates. Advocates are seen to promote healthy planning in relatively weak policy settings, where politicised, largely reactive decisions by individual politicians or practitioners are the main determinants of project success. The most important factor affecting project uptake and implementation is how the ‘problem’ of healthy planning, or what might be considered a healthy planning paradigm, is presented. Such a paradigm includes a strong reliance on the co-benefits of projects; it is also subject to the way that healthy planning is communicated and framed. Potential problems around such a setting are subsequently examined, identifying the potential reasons for the slow delivery of healthy planning.