Background: Usually managed by trained volunteers, crisis helplines services are of primary importance in community care. However, literature has shown that volunteers may be exposed to a high risk of developing negative psychological consequences in relation to the service performed. Although there are numerous studies dedicated to the use of helplines, evidence regarding the experiences of helpers in the context of traumatic losses is still limited. Objective: This study aimed to explore lived experiences of the operators of a crisis line supporting traumatic bereavement. Specifically, it analyzed the psychological impact of interacting with the caller, and the resources and strategies used by the operators themselves. Methods: The study considered 35 operators of the helpline provided by the Italian NGO De Leo Fund, which offers psychological support to survivors of traumatic bereavement. The inclusion criteria were: (a) currently being or having been a helper at the De Leo Fund helpline; and (b) having completed at least 10 shifts in the helpline service. Data were collected through an ad hoc questionnaire, filled online. The thematic analysis technique used Atlas.ti software 8. Results: Four thematic areas emerged from the transcription of the semi-structured interviews. These were: (a) motivation and expectations; (b) emotional and relational impact of the experience as a helper; (c) strategies adopted by operators; and (d) criticalities and strengths. Conclusions: Monitoring helpers’ emotional experiences and the impact of their work overtime emerged in a marked way. The analysis of the strategies and experiences of the operators represents a fundamental factor for the implementation of specific training programs for the management of emergency situations.