This paper will address a number of issues that have arisen from our joint volunteering/research in the Managed Area in Holbeck, Leeds. In October 2014, in response to safety concerns for street sex workers and the increasing need to promote community cohesion between local residents and the key stakeholders, the Leeds Strategic Prostitution Working group introduced the non-enforcement of soliciting legislation in a small area of Holbeck. Prostitution and in particular street based sex work is at the centre of a powerful ideological debate which is polarised, frequently vitriolic and in reality doesn’t address the practicalities of the lives of these street connected women. In this paper we will outline the background against which debates around sex work occur, before exploring two local intervention strategies, which foreground the women who work on the streets of Holbeck. Despite divergent starting points, both projects are motivated by a desire to deliver the best services and as a long-term goal promote transformative systemic change. Street sex workers are affected by a range of health-related issues, not least because the majority of the women we encounter are intravenous heroin users, but also a combination of complex issues revolving around stigma, shame and chaotic housing prevent women from accessing healthcare