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Background and objectives : This study investigated the efficacy of guided self-reflection to strengthen resilience in adults over 50 by exploring the effects of the training on mental health and positive emotional outcomes. Design : A nested clustered-randomized controlled trial was conducted to test the efficacy of the training. Measures occurred at pre-intervention, post-intervention, and at four to five months follow-up. Method: Two samples of participants were recruited. First, older employees from a consumer goods company took part in the clustered-randomized controlled trial. Ninety-three employees (mean age = 54.02 years; 36.56% females) were assigned to the intervention ( n  = 52) or active control ( n  = 41) group. Second, older adults from the community ( n  = 51) were recruited (mean age = 58.63 years; 80.40% female) and assigned to the intervention only. Results : Improvements were observed in the community sample, compared to the active control group, across a range of wellbeing outcomes. When training engagement was used as a moderator, positive benefits for the corporate intervention group emerged for highly engaged participants. Mediation analyses indicated that stress-as-enhancing mindset, stressor benefit, and coping self-efficacy acted as possible mechanisms for change in primary outcomes. Conclusions : Findings provide support for the use of guided self-reflection for resilience training with older adults.