Being an effective and intentional youth practitioner involves more than planning. It includes being able to react intelligently to the many difficult situations that arise. Practitioners in out-of-school and after-school settings regularly confront complex dilemmas that emerge in their daily work. They face situations where competing objectives, values, and warrants come into conflict, situations that can pit the developmental needs of youth, ethical concerns, administrative requirements, and other considerations against each other. Using examples from their research that weigh professional and personal judgments, the authors illustrate the complexity of these practice dilemmas and the considerations program staff included as they responded to these challenging situations.