This study examines how the lasting effects of illegalisation and legal status regularisation contribute to the transformation of aspirations of individuals who lived and worked undocumented for years. It investigates whether obtaining legal residence status opens future possibilities, allowing individuals to project themselves more positively, make plans, and realise their aspirations. Drawing on qualitative longitudinal fieldwork conducted between 2018 and 2022, this research focuses on individuals who transitioned from undocumented status through the “Operation Papyrus” programme in Geneva, Switzerland. The study analyses the dynamic changes in their situations, difficulties, and aspirations, particularly emphasising occupational mobility. The findings reveal that while regularisation initially expands aspirations, various obstacles often necessitate the readjustment of these aspirations over time. This study provides valuable insights into the complexities of enhancing the capability to aspire among vulnerabilised individuals; it also highlights that while policies expanding formal opportunities bring many benefits, they may not be sufficient alone to increase the capacity of individuals to live according to their aspirations, especially for those who were previously exposed to social contexts that prevented them from projecting themselves positively into the future, such as illegalising policies.