In May 1779, a detailed description of an enslaved man named Gloster appeared in the Jamaica Mercury newspaper. This description was written by Gloster’s enslaver, who sought Gloster’s return after he had “runaway” three months prior. The evocative textual content of “runaway” adverts such as Gloster’s has been much analysed by historians; despite the aims of the adverts to capture and re-enslave the individuals they describe, they also pay seldom-seen attention to the individuality of enslaved people. This chapter builds upon a large body of literature considering the evocative textual content of “runaway” adverts but aims to alternatively consider the visual culture of the Gloster’s advert and its context within the Jamaica Mercury newspaper. It examines how the white producers of the Jamaica Mercury newspaper deliberately appealed to the ‘white gaze’ of newspaper readers through the repetition of “runaway” notices and their accompanying illustrations. However, this chapter argues that although these adverts attempt to extend surveillance over enslaved individuals through their visual design, the disconnect between the descriptions of enslaved people in the newspaper and the unknown location of their physical person, ultimately demonstrates a failure to maintain the surveying ‘white gaze.’