Scant research exists on how youth come to attend alternate educational placements. The present study utilized a multiple case study design to retroactively examine the course of developmental trajectories toward placement in secondary Alternate Program Schools. Participants were selected using criterion sampling, on the basis of having a son or daughter aged 12 through 16 years attending a secondary Alternate Program School at the time of data collection. The study focused on six youth aged 13 through 16 years. Examination focused on: (a) youth characteristics; (b) psychosocial history (e.g., general, and parental/familial including educational history, history of mental illness and/or problem drug or alcohol use, and history of trouble with the law); (c) developmental history; (d) medical/health history; and (e) educational history. Data collection involved semi-structured interviews with at least one parent, as well as a review of the youth's educational files. Data was coded using the computer program HyperRESEARCH 2.6, and analyzed within each case and across cases. Emerging themes and recurrent events were categorized. Implications for practitioners and researchers are discussed so as to inform practice, and future directions for research are indicated.