Purpose: Assisting asylum applicants through their procedure for international protection implies a commitment that most caseworkers accept with deep satisfaction. However, working with asylum applicants who disclose the claim for protection and stories of their journey can be challenging and distressing. The study aimed to understand the experience of caseworkers with the asylum applicants in Lesvos, specifically, the challenges they face and their perception of the qualities that facilitated or inhibited coping. Method: A grounded theory analysis within a constructivist framework involved interviews with thirteen caseworkers, cultural mediators, and operations officers in Levos and Malta. Findings: A two-phase analysis was conducted due to unexpected findings. The first phase of the analysis uncovered the challenges posed by the work itself, and the caseworkers' personal characteristics which were either helping or hindering addressing these challenges. The second analysis revealed a four-step process as perceived by the asylum caseworkers: starting from the workcontext, facingchallenges, finding ways torespondto them, and finally, theeffectthat this process had on the caseworkers' perspective about themselves and life. Conclusion: For those who developed adaptative coping, interviews indicated a process of transformation in the caseworkers' perception, a new sense of self and world view, including the development of self-awareness, personal power, the relation to work and the refugees, and a deeper cultural understanding. Recommendations are provided for caseworkers' mental-health and operational support as well as for future research.