In Western countries, the loss of jobs among older workers is a highly worrisome situation, since it can be synonymous with long-term employment precariousness and definitive exclusion from the labour market. This precariousness is occurring while the labour force in these countries is aging, and governments are looking to extend people’s working lives. It is therefore particularly relevant to study different labour market reintegration processes and to understand their sustainability from a psychological perspective. The present article is examining these processes using a longitudinal study over an 18-month period with 61 older Canadian workers. Time 1 and Final Time were documented with semi-structured individual interviews. These data allowed us to qualitatively construct three reintegration processes (blocked, downgrading, and sustainable) that describe a large spectrum of workers’ experiences regarding occupational repositioning. Quantitative analyses likewise suggest moderate statistical links between the reintegration process and changes in subjective variables associated with the relationship to work and identity representations. Altogether, the results underline the importance of returning to the labour market in qualified, decent, sustainable work that allows people to have a decent and meaningful personal life. The results also suggest, in keeping with the psychology of sustainability, that interventions should promote occupational and personal enrichment, both at the individual and organizational levels.