This report details a research project conducted by SCU academics in partnership with the End Street Sleeping Collaboration which examined the homelessness service system in Sydney, NSW, from the perspective of people with lived experiences of homelessness (particularly rough sleeping) and frontline workers in non-government Specialist Homelessness Services (SHS). While the findings highlight some positive aspects of the current homelessness service system, they also demonstrate significant limitations with regards to the treatment of rough sleepers - particularly by government housing services – as well as diminished access to housing (both short and long term) and inadequate supports. From these findings, the report makes a number of recommendations to improve service delivery and achieve more sustainable housing outcomes for people who have experienced rough sleeping and other forms of chronic homelessness.