Literature on the experience of the bereaved during the COVID-19 pandemic suggests how complicated it has been for those who lost loved ones. However, the sense of grief experienced by those who journey with them is relatively unexplored. The present study examines vicarious experiences of grief of healthcare workers, faith-based workers and mental health workers who worked with the bereaved due to COVID-19 deaths. The study was done in two phases. In the first phase, a survey showed that compared to other helping professionals, healthcare workers reported the highest levels of vicarious grief. In the second phase, in-depth interviews revealed five themes: acknowledging contexts of grief, navigating relations with the bereaved, sharing others’ grief, internalizing encounters, and negotiating challenges. Findings highlight the need for supportive interventions at the organizational level.