Lowered academic achievement and premature departure from high school continue to plague the educational system, creating the need for greater insight into experiences affecting students' classroom performance. Much is known about academic achievement; however, less research has focused on the role of familial attachment on premature departure from high school. Guided by attachment theory, the purpose of this interpretative phenomenological study was to gain insight into General Education Diploma (GED) students' familial attachment experiences influencing premature departure from high school. The research questions focused on GED students' primary caregiver and educational experiences. Participants (n = 14) consisted of current or previous GED students 18-30 years of age. Data were gathered from semistructured interviews and a Life Map used to capture expression of feelings through symbols. Interview transcriptions were hand-coded by bracketing words and phrases for composite textual descriptions. Data interpretations were bolstered by committee member checking and participants' review of extracted data. Findings revealed a close connection between the types of attachment formed with primary caregivers and early departure from high school, but participants were more strongly influenced by external influences such as relationship conflicts, health crises, domestic violence, abuse, loss, and paternal abandonment. This study offers insight to educators, counselors, and those within the criminal justice system on these students' emotional and mental needs.