The rhetoric surrounding the transportation of prisoners to the Straits Settlements and the reformative capacity of the penal labor regime assumed a uniform subject, an impoverished criminal, who could be disciplined and accordingly civilized through labor. Stamford Raffles, as lieutenant governor of Benkulen, believed that upon realizing the advantages of the new colony, criminals would willingly become settlers. These two colonial prerogatives of labor and population categorized transportees into laboring classes where their exploitation supposedly brought mutual benefit. The colonized was collectively homogenized as a class of laborers and evidence to the contrary, of politically challenging and resistant individuals was suppressed. This paper focuses on two prisoners who were incriminated during the anti-colonial rebellions of the mid-nineteenth century and were transported to the Straits Settlements. Nihal Singh, a political prisoner from Lahore, was incarcerated in isolation to prevent his martyrdom and denied the supposed benefits of labor reform. Conversely, Tikiri Banda Dunuwille, a lawyer from Ceylon was sent to labor in Melaka as a form of humiliation. Tikiri’s many schemes to evade labor damned him in the eyes of the authorities. The personal histories of these two individuals expose how colonial penal policy recognized and manipulated individual differences during a time of rising anti-colonial sentiment. The experiences of these prisoners, the response of their communities and the voices of their descendents offer us a very different entry point into colonial penal history.