My research has developed an alternative approach to depicting the nuances of homeless experiences in Sydney, Australia. Homelessness is a complex issue with a range of factors contributing to the rising numbers of people affected annually. Rough sleeping embodies one lived experience of the issue; however, this accounts for less than 10% of the homeless population in Australia. Despite this, rough sleeping is widely used to portray the issue through awareness raising campaigns and other representations of the issue in graphic design, as seen in recent work by organisations offering support to people experiencing homelessness, such as the Exodus Foundation and Mission Australia. Such portrayals have been shown to perpetuate negative stigma and stereotypes surrounding the issue of homelessness as a whole. Drawing from recent insights about design’s capacity to enact agonistic pluralism by design researcher Carl DiSalvo, my research reveals what is omitted in contemporary mainstream depictions of homelessness. Using cultural probes that explored the nuances of homelessness with people currently experiencing the issue, the research discusses the resulting poster series and website I have designed for the purpose of creating a more informed public debate and understanding regarding the conditions of homelessness and those affected by it in Sydney.