This chapter explores the activities, debates, and discourses on prostitution throughout the nineteenth century. It is suggested that in order to cast the ‘prostitute’ as a suitable object of charity and compassion reformers generated what Edward Bristow calls a ‘cult of sentimentality’ around the figure of the ‘prostitute’, whom they featured as a helpless victim of seduction or social injustice, ‘more sinned against than sinning’. The initial connection between philanthropists and ‘prostitutes’ lay in the former’s activities in the prison reform movement. Developments in the penal system throughout the preceding centuries led to an increase in the number of people incarcerated for a wider range of offences, many of whom would have been reprimanded, fined, whipped, or sent back to their masters and not imprisoned earlier in the century. The philanthropic and medical discourses represent many branches of voluntary initiatives to reform the ‘fallen’.