There has been a lot of research on the relationship between regulators and street vendors, often portraying regulators as bullies of vulnerable vendors. However, there is little documentation on urban regulators and their challenges as they implement their mandates. This paper investigates the challenges and negotiating strategies of regulators of street-vended foods in Ghana and analyses the implication for their relationship with street food vendors. The paper reveals that regulators operate in a context of limited resources, leading to a general feeling of neglect. In coping, regulators adopt strategies that encourage harassment of vendors and increase tensions between vendors and regulators. Thus, this study establishes relations between the challenges and negotiating strategies of regulators and the poor relations that exist between regulators and vendors. This paper argues that motivating and addressing the needs of regulators can serve as an important basis for eliminating harassment and for improving the relationships between regulators and street vendors.