The ‘Windrush’ generation of Caribbean migrants are among almost 600,000 Commonwealth migrants who arrived in the United Kingdom before 1971. Having lived and worked in Britain for most of their lives and having a legal right to British citizenship but sometimes lacking documentation to prove this, there is continued public outrage in 2018 in response to stories of detention, deportation, denial of services and loss of jobs which had occurred as a result of new immigration rules. Many argued that these hardships were a foreseeable result of Britain’s ‘hostile environment’. The scandal resulted in the resignation of the Home Secretary, but it remains to be seen what, if any, changes will be made to the laws and policies responsible. The experiences of the Windrush generation are worthy of analysis because of their position both as British citizens and visible minorities. Moreover, as the British Government makes plans for EU citizens who are present in the UK to apply for ‘settled status’ after Brexit, the construction of citizenship and belonging are particularly salient. This dissertation examines the role of ‘hostile environment’ policies in perpetuating Britain’s racialized law enforcement. In doing so, it contributes to the crimmigration field whilst providing a contemporary application of it’s analytical power.