The serious illness or death of a caregiver are two of the most distressing events that can befall a child, and are often temporally linked. Although both adversities may impact children’s mental health, studies have not yet attempted to disentangle the effects of parental illness versus those of parental death with regard to children’s psychological functioning. Further, there has been little empirical investigation of potential factors that may diminish risk for psychopathology following either of these adversities. The current study evaluated levels of anxiety, depression, and posttraumatic stress symptoms (PTSS) in youth age 7–13 grappling with either parental cancer (N = 31) or parental death (N = 32) and examined potential predictors of these mental health outcomes across both groups of children. Youth contending with parental cancer exhibited lower levels of PTSS than children who had experienced the death of a parent, but both groups exhibited similar levels of anxiety and depression. Expressive coping was associated with lower levels of PTSS, anxiety, and depression across both groups. An interaction effect revealed that for the bereaved group only, positive parental reinforcement and supportive caregiver communication were inversely associated with PTSS. These findings provide a foundation for future work designed to identify factors associated with distinct mental health outcomes among children facing parental cancer and/or parental death.