Over the past decade, most major Canadian municipalities have been involved in the development of formalized systems-level collaborative approaches to addressing homelessness and housing issues. The implementation of such approaches has been widespread and, to some extent, standardized based on the design of ‘community advisory boards’ (CABs) mandated and created by the federal government through the Homelessness Partnering Secretariat (HPS). These committees have significantly affected systems-level strategic planning to address homelessness in urban, rural and remote areas across the country. Despite marked impact and some success, these groups also face challenges related to effective collaboration and governance. In this chapter we explore the multiple and diverse aspects of systems-level homelessness collaboration in Canada. First we trace the history of formalized, local systems-level collaboration to address homelessness in Canada. This is followed by an examination of international literature and applications to provide some direction for future growth and preliminary reflections on the benefit to process and effect evaluation for homelessness collaboratives.