This paper addresses the complex and ambivalent interplay between experiences of irregular migration and asylum seeking in the Italian context. Drawing on ethnographic research carried out in the city of Bologna, I analyse some institutional encounters between migrants seeking asylum and bureaucrats, in an attempt to highlight the contradictory and dynamic nature of a set of categories, laws and policies. Bureaucratic labels such as ‘irregular migrant’, ‘asylum seeker’, ‘Dublin case’, etc., represent intersubjective social constructions, simultaneously ascribed to individuals and actively performed by them. The multiple shifts between different ‘legal’ and ‘illegal’ conditions are shaped by the interactions between immigration laws and policies, local bureaucratic practices and individual experiences. By analysing the morally dense, and unspoken, categories embedded in these processes, I argue that in contemporary Italy asylum seekers are constructed as flexible non-citizens, subjects floating between transient juridical statuses, but consistently kept at the margins of society. Furthermore, I show how asylum seekers themselves can try to perform, transform or subvert the (il)legal and moral categories imposed on them.