Krishna Hutheesing, a member of the renowned Nehru family, was one of the prominent upper-class women of the early twentieth century. She actively participated in the non-violent Gandhian movements during the anti-colonial struggle against British rule in India and was imprisoned twice. Her autobiography and prison diary offer reflections on her prison experiences. These narratives also serve as accounts of the refashioning of ‘self’ within the political nationalism of the twentieth century. They also offer insights into prison conditions in colonial India and raise questions about the exploitation women endure both within and outside prison walls. I would argue that when analyzed critically, these texts reveal differential treatment accorded to ‘politicals’ in comparison to common prisoners in British Indian jails in the twentieth century. By employing Kamala Visweswaran’s analytical framework of the ‘gendered relation of subalternity’, this chapter explores questions of differential and mediated agency in subaltern speech.