Sustainability is vital to the success of our cities and settlements. While communities are becoming increasingly conversant with sustainability concepts, uncertainty remains over how to translate these into planning practice. This practicum explores the role of sustainability checklists as one tool for planning and designing more sustainable communities. The inquiry examines the design, implementation and effectiveness of these tools and seeks to understand the motivation and context in which they are developed, the varying approaches and components of checklist tools, and the impact that they are having on planning and development practices. A review of twenty-four sustainability checklists from a selection of BC municipalities, an online survey and key informant interviews were used to inform this study. Nine key findings are identified suggesting that while checklists are helping to communicate sustainability objectives and are encouraging better development, they are not resulting in the large scale shifts to development patterns and urban systems that are required to achieve sustainable outcomes; therefore, checklists need to be integrated with other policies, regulations and tools in order to assist in achieving sustainable settlements.