While the process of gentrification has been one of the most hotly debated in academia this discussion has been dominated by select voices and disciplines. Little been written from the point of view of the urban planner or explicitly regarding built form and land use. This study firmly situates the planner in the gentrification discussion by analyzing three planning interventions in Toronto's Downtown West. The study's purpose is to provide a clearer understanding of the planner's role and abilities when planning for neighbourhoods facing upscale change. In addition to the case studies, the study provides a general overview of the historical gentrification literature, highlighting what aspects the planner ought to be most concerned about. The study concludes by providing a summary of the inventory of the tools used by the planner in these cases, as well as challenges, problems. and opportunities raised by these cases.