Turner in 2014 described system planning within a Housing First context as “a method of organizing and delivering service, housing and programs that coordinates diverse resources to ensure that efforts align with homelessness-reduction goals” (p. 7). In this chapter I take up this understanding of system planning and apply it to a case study of CHF’s System Planning Framework (CHF, 2014), a tool created as one component of the overall system’s approach to ending homelessness in Calgary. The intention is to share learnings which may be helpful to community leaders and service providers as more and more cities across the country make commitments to end or reduce homelessness.