This chapter focuses on the gender dimension of remittance transportation particularly the encounters of women with remittance transporters who are mainly men. The chapter highlights how women remitters have had to navigate the risky streets of Hillbrow as they are forced to locate the remittance transporters to send home their hard-earned remittances. The chapter presents narratives on the different ways in which women in the diaspora negotiate the risks associated with the remittance transportation spaces. The core argument of the chapter relates to how women tend to get undermined within the highly masculinised remittance transportation spaces. In these spaces not only are women victims of various forms of crime, verbal and physical abuse, but they are also the victims of exploitation and dishonesty. The chapter is a result of ongoing ethnographic research that has evolved since March 2018 and has involved conducting observations and informal interviews in Hillbrow, the hub of remittance transportation. Theoretically, the chapter draws from the works of Federici on feminism.