Young migrants in resource-constrained settings face multiple challenges when they move away from home for work and try to make their way in a new place. In Uganda, with a growing youthful population increasing numbers of young people are leaving home to look for opportunities in urban areas, often facing a precarious existence as they try to make money. Using data from in-depth interviews we investigate the lived experience of precarity of 20 young men who had recently migrated to a small town in south-west Uganda. We adopt a case study approach to look in-depth at the experience of three of the young men, showing how they engage in a continual evaluation of risk in their day to day lives, as they face multiple challenges related to their insecure employment and poor access to health services. We found that the risks that the young men are willing to take to maximise their limited opportunities changed over time. Our findings provide valuable insights into the gendered risks faced by young male migrants and illustrate the ways in which young migrants, many of whom may only have travelled a relatively short distance from home, face risks and challenges to their health and wellbeing, and need to be recognised as a population in need of attention and support.