Losing a loved one is a fundamental and ubiquitous life experience that is often characterized by a certain period of grief and emotional distress. Although the majority of the bereaved can cope with grief resiliently, around 1 of 10 individuals could experience an unusually protracted and intense response referred to as prolonged grief disorder (PGD) following death of a loved one. PGD is associated with work and social impairment and heightened risk of severe medical and psychological conditions. Current means of diagnosis requires a minimum of 6 months to confirm and identify PGD and is discrepant with the fact that the bereaved may need psychotherapeutic intervention in a more timely manner. Contemporary studies have outlined prospective risk factors that could cause poor bereavement outcome, which can potentially contribute to early identification and prevention of problematic response to grief. Self-monitoring applications have been developed and broadly implemented in a vast spectrum of mental and health-related interventions and self-managing processes. This study presents the conceptualization and development of an Internet-based screening method designed by the researchers and psychotherapists that aims to provide meaningful and quantitative feedback in the early phase of the grief and to support decision making in the bereavement process through monitoring the susceptibility to problematic grief outcome.