Professionals are in good standing in the principal-agent literature. With a sense of professional responsibility, an honor code or an oath, they bring extra effort to challenging and difficult to monitor tasks. Often they repay our trust. But there are also substantial challenges in delegating to those with difficult to replace knowledge and specialized training. These challenges are discussed in this chapter in a variety of individual and organizational contexts and in particular in analyzing the use that religious institutions and governments make of those with specialized training. Notwithstanding their rigidly hierarchical organizational structures, complete with rules of conduct and quite fearsome methods of control, the Catholic Church and the military have difficulty keeping agents on task. The chapter shows how these agents exploit their positions. Observing the theoretically unexpected passivity of principals when confronted with non-compliant behavior in these organizations, this chapter modifies the accepted account with the argument that group loyalties, asset specificity, and what the author refers to as the “agent confidence factor” put up the cost of punishment for the principal and protect noncompliant agents from the normal consequences of their actions.