The colonial state interacted with deviant sexuality such as same-sex behaviour, transvestism, and transgenderism in multiple ways. Structures of violence were always inherent in these interactions including physical pain but also epistemic and discursive violence. This chapter aims at interrogating the historical entanglement of male and transgender sexual deviance and state violence by analyzing three instances in which the colonial state intervened in the lives of sexually deviant male colonial subjects. After the enactment of the Indian Penal Code (IPC) in the year 1862 same-sex intercourse was made criminal and prosecuted as a major offence. Similarly, rape offences came under closer scrutiny by the new legal regime. Paradoxically, possible asymmetrical and violent characteristics of same-sex sexual relationships were negated by the IPC. While the female in a rape case could count as a victim, the two parties in a male same-sex relation on record – that might have been violently forced or not – were labelled as ‘active’ and ‘passive agents’, thus precluding the notion of victimhood in those instances. The colonial legal system in this manner created a double standard for prosecuting violence in sexual relations that continues to influence jurisprudence in contemporary India. This double standard for prosecuting violence in sexual relations was particularly obvious when male children or juveniles were involved. They were conceptualised as ‘immoral’ themselves by the judicial discourse after having (non-consensual) contact with adult men. Those boys posed a threat to the colonial moral order due to their alleged contaminated nature and had thus to be treated with specific measures such as whipping and separate placing in Salvation Army settlements instead of ordinary jails. Part II of the 1871 Criminal Tribes Act included ‘eunuchs’ as one of the groups that needed monitoring due to their alleged criminal inclinations. The category ‘eunuch’ encompassed a variety of sexually deviant men and transgender individuals but was mainly operated to target men who dressed in female attire in public and thus threatened colonial gender orders. In the accompanying process of criminalization and (not always successful) attempts at regulating them, sexually deviant men were scrutinised under a colonial police and medical regime that violently disrupted the lives of those individuals. The 1921/22 Jail Report triggered a debate about the desirability of upholding the penal settlement on the Andaman Islands due to the alleged prevalence of ‘unnatural vice’ amongst the convict society. This was not only seen as problematic because of the obvious moral (double) standards of the colonial regime but also due to the supposed linkage between male-male sexual desire, feelings of jealousy, and murderous assaults between convicts. Close analysis of the judicial files concerned with those murder cases reveals a specific colonial understanding of deviant male sexuality which combined a certain sexual identity and the proclivity towards interpersonal violence. This section will also analyse various instances of colonial violence against sexually deviant men in prisons. This included the invention of the disciplining technology of the ‘Indian cubicle’ for convicted ‘sodomites’, a cage-like iron construction which was supposed to be built into the common dormitories to enable separation of male convicts during the night and which left violent marks on the bodies of the convicts so confined. I will also elaborate on more unofficial forms of violent punishments within the prisons, such as the mimicking of sexual violence. The three examples can illustrate how, on the one hand, colonial discourses about male sexual deviance depended heavily on the terminology of violence, and, on the other hand, created violent disruptions for the people thus labelled.