Bereaved high school adolescents are often affected in a myriad of ways by the death of a loved one. The traumatic experience and bereavement process add complexity to high school adolescents’ development and this phenomenon is not fully understood, in particular in regards to communication and relationships in the school environment. The conceptual framework of this study is based on Kubler-Ross’s stages of loss and Sergiovanni’s concept of schools as communities. This retrospective study explored adult perceptions of their grieving in the high school setting with a focus on understanding how relationships and communication within the school environment impacted the bereaved adolescents. For this qualitative phenomenological inquiry, 3 interviews were conducted with 6 women and 1 man ages 23 to 66, using a convenience sample. The serial interview process allowed repeated coding for emergent themes, which improved interview questions and deepened the thematic analysis. Member checking provided a check and balance system for assessing the accuracy of the interpretations. The participants’ perceived the support of friends to be the most helpful in the school environment; teachers supported them to a lesser degree, and school counselors provided the least support. The participants’ also perceived grief counseling from school counselors as important support for students in the high school environment in today’s schools. This study promotes positive social change by providing insight into ways in which adults in the school environment may assist grieving students, and thereby may reduce the need for social services in the future in a society experiencing increasing mental health costs.