Prison administration has changed dramatically in recent years. The warden of 25 years ago was the overseer of an attempt to achieve reformation of character through isolation, hard work, and repentance. Today's superintendent must manage complex personnel systems, overcrowded institutions, and technological advances in a context of increased public and political scrutiny and close legal oversight. Nobody 25 years ago could have foreseen the massive involvement of Federal courts in prison oversight, the rapid recent proliferation of private prisons, or the politicization of criminal justice policy. The most important challenges of the past 25 years were unforeseeable; the most important challenges for the next quarter century are probably unforeseeable as well. Possible influences include the continued and growing economic disparities between suburban and urban residents, changing demographics, public attitudes toward drugs, advances in drug treatment, the effects of the move to the information/technology age, the role of the courts, external events such as wars or prison riots, and potential changes in the organization of prison administration. 20 references (Author abstract modified)