In many countries, eldercare workers are approaching retirement. To remain attractive to older and experienced workers, organizations need to understand how employees nearing retirement think about and experience theirwork situation. This qualitative study investigated how older nursing assistants within residential care for older people experienced aging at work, their psychosocial work environment, and their late-career planning. Semistructured interviews with eight nursing assistants (aged 55–61 years) in Sweden were analyzed using an Interpretative Phenomenological Analysis approach. The results show that the psychosocial work environment was perceived as stressful and considered a long-term health risk, and that (future) health and work ability were key factors determining nursing assistants' late-career planning. Moreover, personal resources and social support from colleagues seemed protective against job demands. Aspects considered in late-career planning also included personal finances and meaningfulness of work. While these findings may be sample-specific, they still provide insights into the experiences of an important occupational group. This means that the findings can be useful for organizations aiming at promoting successful and sustainable aging-in-workplace and encouraging extended working lives.