We examined variables that might identify at-risk individuals following the death of a significant other. Previous research indicates attachment anxiety is associated with more intense grief, while avoidant individuals seem to cope with loss as well as secure individuals. Participants in this study (368 adults aged 17–49) completed an online survey measuring general and relationship-specific attachment insecurities, relationship characteristics, loss circumstances, and typical and prolonged grief symptoms. General attachment anxiety and avoidance were related to prolonged grief symptoms but not to typical symptoms. Relationship-specific anxiety was positively related to grief symptoms, while specific avoidance was negatively related. The results support the distinction between general and specific attachment insecurities and between normative and prolonged grief reactions.