This chapter uses poor law, census, police, magistrates and prison records relating to over eight-hundred women, alongside in-depth case studies of individuals, to examine the major themes that shaped the lives of women involved in prostitution in Scotland during the early twentieth century. The chapter explores various reasons why women entered or exited prostitution at certain stages during their lives; particularly their socio-economic backgrounds, their health, use of alcohol or involvement in crime and other events that shaped their lives and relationships, including the different types of relationships that existed among ‘prostitutes’, ‘pimps’ and ‘brothel-keepers. Despite the limitations of the available sources which are heavily mediated, this collective biography approach provides some important insights into the lives and experiences of the women involved in prostitution. Importantly, this evidence begins to reveal a level of women’s historical agency that has often been difficult for historians to ascertain.