The arrival of large numbers of Central and Eastern European migrants to the UK has been met with political and public debate around the perceived impacts on indigenous labour market opportunities coupled with fears about the demands placed on the welfare system. Within this broader migration, the arrival of Roma has triggered particularly prejudicial reactions. However, little is known about how Roma experience the social security system within the UK, particularly within a situation of increasingly conditional rights for European migrants. This chapter begins by highlighting some of the pervasive narratives in relation to Roma that focus on their supposed disproportionate representation within benefits systems and the subsequent responses of Member States to such (mis)representations. Drawing upon interviews with Roma migrants claiming social security benefits in the UK, the chapter then provides insights into how they respond to the conditionality inherent within the UK social security system. The chapter highlights that, contrary to pervasive narratives, claiming benefits appears to be a last resort after multiple job search attempts. Furthermore, welfare conditionality has the potential to lead Roma to disengage with the benefits system altogether and seek informal employment in order to meet their basic needs.