A classification system collects, stores, and analyzes data which trigger administrative actions that shape the conditions of confinement, punishment, and program participation. The process study of four jail classification systems shows that attempts to reform or formalize classification decisions are thwarted because (1) criteria are ambiguously stated, (2) the model or criteria are not properly communicated to staff and inmates, and (3) classification decisions are subverted by lack of space and services within the jail. Jail crowding is the most damaging and pervasive of these impediments. Jail administrators and staff often perceive themselves as helpless victims at the mercy of political and economic factors that fuel the overcrowding problem. Improved classification criteria, properly communicated to staff and inmates, represent the more easily accomplished administrative reforms to improve classification; however, jail classification cannot be achieved until the jails are depopulated and upgraded to minimum standards in all areas of the facilities operations. The road to solving jail overcrowding and improper classification is a political process. It includes securing legislatively mandated jail capacity limits, greater authority to cite misdemeanors and felons, expansion of minimum and medium security settings, and sufficient fiscal resources to meet minimum standards. These reforms will not be achieved unless jail administrators are willing to seek them in the political arena, abandoning their traditional passive political stance. Tabular data and three references are provided.