Objectives: Mindfulness-based interventions demonstrate promise in helping individuals cultivate awareness of risks, thereby decreasing likelihood of revictimisation; however, mindfulness-based approaches with homeless youth have received little empirical attention. This mixed-methods study investigates a mindfulness-based intervention for homeless youth, investigating (a) quantitatively - to what extent is the intervention effective in increasing youths’ mindfulness over time? and (b) qualitatively - in observing homeless youths’ participation in the mindfulness groups, what strategies appear most helpful in engaging them in this mindfulness intervention and what challenges are encountered? Methods: Using a randomised experimental design, the current study pilot tests an intensive (3 day), skill-building intervention to train homeless youth (N = 97, ages 18–21 years) to practice mindfulness and avoid risks. Youths’ mindfulness was assessed via standardised self-report instruments at baseline and post-intervention (1 week post baseline for youth in the control condition). Results: Repeated-measures ANOVA results indicate that although no effect was found on total mindfulness, a significant effect was found for mindfulness subscales. Intervention youth improved in their observation skills significantly more than control youth (F = 3.88, p < .05, partial-?2 = .05). Qualitatively, certain intervention strategies (i.e., facilitating, personal sharing, teaching, and peer activation) demonstrated notable utility in actively engaging youth in mindfulness material, whereas challenges (meeting basic needs, a fight or flight instinct, and a generalised distrust of service providers) created challenges in implementing mindfulness skills. Conclusion: The intervention improved youths’ attention to internal and external stimuli yet future iterations will need to continue to modify to meet the unique needs of this population.