Prolonged grief (PG) is a mental health condition characterized by severe distress following a loss. This study examines the roles of attachment styles, social support, stressful life events (SLEs), and pre-existing psychopathology in predicting PG and post-bereavement psychopathology among 74 caregivers of palliative patients. Using validated assessment tools, the study employed hierarchical regression and fuzzy-set qualitative comparative analysis (fsQCA) to identify predictors of prolonged grief and psychological outcomes over six months. Results showed that pre-existing psychopathology and PG risk predicted post-bereavement psychopathology, though not PG itself. Low social support and high SLEs were linked to worse outcomes, while strong social support and low stress predicted positive outcomes. These findings highlight the importance of multiple interacting factors in understanding grief and emphasize the need for interventions that enhance social support, manage stress, and address mental health conditions to reduce psychological distress in bereaved caregivers.