The vulnerability of street-involved children and youth (SICY) in sub-Saharan Africa (SSA) to adverse childhood events is well documented. Associations between orphanhood and multiple types of vulnerability have also been demonstrated. Whether type of orphanhood is associated with adverse events experienced during childhood or is predictive of psychosocial health is still unclear. Maua Methodist Hospital conducted a cross-sectional survey of 53 semi-rural SICY. Multiple indicators of vulnerability, including educational attainment, income, food security, adverse childhood events and psychosocial health (resilience, self-esteem, depression and self-efficacy), were analysed to determine differences between orphan status groups. Though not statistically significant, paternal and double orphans reported several factors that suggested greater vulnerability to adverse experiences and outcomes on the streets. Maternal and double orphans reported significantly more adverse childhood experiences than paternal orphans, suggesting survival of the mother may be a protective factor. Double orphans had significantly higher depression scores than each of the other orphan groups. Within a rescue and rehabilitation program, children who have lost both parents may need extra psychological support and intervention. Paternal and double orphans still living on the street may face greater obstacles to escaping street life and are a high priority for both prevention and intervention programming.