There exists a voluminous literature on the history of vagrancy and vagrancy legislation. However, virtually all of its focus has been on the manifestations of vagrancy as a social problem. What has not received attention is another important aspect to this history, one that finds its roots and geneses directly out of its construction as a social problem. This is the problem associated with the logistics surrounding the administration of punishment within correctional institutions, what I call vagrancy as a penal problem. The day-to-day operations of the criminal justice system, especially that part which was responsible for the administration of punishment, were immensely burdened because of the sheer number of vagrants who came through the system. This created logistical problems with respect to housing, classifying, maintaining and regulating prisoners, and especially with respect to vagrants, putting them to hard labour. This paper seeks to elucidate the penal problem of vagrancy by narrating the voices of the personnel who worked in correctional institutions.