The concept of the “writer flâneur”, as developed by Walter Benjamin, sought to make sense of the seemingly chaotic nineteenth century city. While the flâneur provided a way for new urban structures to be ordered, it was also a transgressive act that involved engaging with urban spaces in new ways. In the contemporary city, where spaces are now heavily controlled and ordered, some members of the city’s socio-ecological community suffer as a result of idealistic notions of who and what belongs in the city, and how we must behave as urban citizens. Many of these ideals emerge from nineteenth century conceptions of the city in contrast to the country (Williams). However, a reimagining of the flâneur can allow for new transgressions of urban space and result in new literary imaginaries that capture the complexity of urban environments, question some of the more damaging processes and systems, offer new ways of connecting with the city, and propose alternative ways of living with the non-human in such places. With reference to the work of Debra Benita Shaw, Rob Shields and Donna Haraway, I will examine how the urban walking figure might be reimagined as cyborg, complicating boundaries between the real and imagined, the organic and inorganic, and between the human and non-human (Haraway Cyborgs). I will argue that the cyborg flâneur allows for new ways of writing and reading the urban and can work to reimagine the city as posthuman multispecies community. As one example of cyborg flânerie, I look to the app Story City to show how a writer can develop new environmental imaginaries in situ as an act of resistance against the anthropocentric ordering of the city. This article intends to begin a conversation about the ethical, political and epistemological potential of cyborg flânerie and leads to several questions which will require further research.