In the latter decades of the eighteenth century, thousands of inmates were sentenced to the prison workhouse at Christianshavn for crimes ranging from begging and vagrancy to theft and even murder. Situated between the system of poor relief and the penal system, the prison was a complicated, almost hybrid institution featuring both disciplinary and caring obligations to its inmates. Although the inmates shared a common relationship to the authorities and the same constraints of navigating a system of coercion in their favor, their experiences varied greatly. From the perspective of three inmates’ experiences within the prison workhouse and inspired by Michel de Certeau’s concept of tactics and strategies, this chapter examines different experiences of imprisonment. By exploring the differences of experience in the prison workhouse, the chapter underlines the plurality of shared experiences for a more complex and contextual understanding of the ever-evolving prison system.