Homeless youth represent a chronically vulnerable segment of society whose mental health needs, despite their acuity and complexity, are often unmet. This article describes the development and implementation of a pilot mental health group intervention, the Housing Outreach Project–Collaborative Wellness and Mindfulness Group, for young people in their first year of transitioning from homelessness/precarious housing to independent living. The intervention aimed to provide evidence-based mental health support to a traditionally difficult to engage population. The development of group framework and content, implementation, resultant client engagement, and perceived successes and challenges are described. Considerations for future mental health interventions and research with this population are discussed.