Welfare to work interventions seek to move out‐of‐work individuals from claiming unemployment benefits towards paid work. However, previous research has highlighted that for over‐50s, particularly those with chronic health conditions, participation in such activities are less likely to result in a return to work. Using longitudinal semi‐structured interviews, we followed 26 over‐50s during their experience of a mandated welfare to work intervention (the Work Programme) in the United Kingdom. Focusing on their perception of suitability, we utilise and adapt Candidacy Theory to explore how previous experiences of work, health, and interaction with staff (both in the intervention, and with healthcare practitioners) influence these perceptions. Despite many participants acknowledging the benefit of work, many described a pessimism regarding their own ability to return to work in the future, and therefore their lack of suitability for this intervention. This was particularly felt by those with chronic health conditions, who reflected on difficulties with managing their conditions (e.g., attending appointments, adhering to treatment regimens). By adapting Candidacy Theory, we highlighted the ways that mandatory intervention was navigated by all the participants, and how some discussed attempts to remove themselves from this intervention. We also discuss the role played by decision makers such as employment‐support staff and healthcare practitioners in supporting or contesting these feelings. Findings suggest that greater effort is required by policy makers to understand the lived experience of chronic illness in terms of ability to RTW, and the importance of inter‐agency work in shaping perceptions of those involved.