Drawing on data from seven European countries (Czech Republic, Finland, France, Germany, Ireland, Italy and the United Kingdom), this article seeks to identify how young migrant men engage with authority and avoid conflict against a backdrop of increasing hostility towards migrants in many European countries. As this article contends, even those with permanent residency status in the host country often find themselves having to justify their legitimacy to carry out daily tasks, resulting in many young male migrants living with feelings of perpetual insecurity. As such, a number of coping strategies are employed by young migrant men in order to assuage such feelings and mitigate potential risks. Focusing on the lived experiences of this group, as described in narrative interviews, our study found that many young migrant men are required to enter into negotiations with authority figures, where there is a considerable power differential. Acting as risk assessors, they find themselves forced to navigate complex and challenging social relations and support networks. We show how self-limiting behaviour intended to avoid or control interactions with authority and the negotiations conducted to minimize the risk of ‘trouble’ by young migrant men not only are problematic in the context of day-to-day activities but can very often have a detrimental impact on their lives.