Effective group programs with challenging youth need to be grounded in a clear understanding of core principles that guide effective practice. This article examines the operating philosophy of an established outdoor education and therapy program which combines the Re-ED philosophy of Nicholas Hobbs (1994) with adventure education developed by Campbell Loughmiller (1965, 1979). Key practice principles which are essential to the operation of successful values-driven interventions with troubled and troubling youth are described.