The focus of this study is on reconstructing the history of Prison in Agäw Meder Awrajja from 1941 to 1991. It examines the history and development of punishments and corrections. Methodologically, the thesis exhaustively exploited archival, oral, and written secondary sources. The principal method employed in the study is the qualitative method. Like their Christian counterparts, the pagan rulers of Agaws in Gojjam had a tradition of keeping some of their most dangerous and mutinous opponents or political and religious enemies on the ambas (mountaintops) during the medieval period. However, a new regime of incarceration, which is different in many ways from that of the amba prison, began to take shape in Agäw Meder in the twentieth century, particularly in 1942. This resulted from the reaction to the modernist impulses of the imperial state for centralized and uniform enforcement of law and order and maintenance of social and civil peace. Novel constitutional and legal frameworks underpinning the system were created. Similarly, new bureaucracy, physical infrastructure, modalities of penal labor, and methods of holding and disciplining prisoners were also brought into operation. Starting from humble beginnings in the post liberation period, the Agäw Meder Awrajja prison discharged over the years the vital functions of holding remand and serving prisoners. Moreover, it also played a part in the growth and expansion of the town by providing cheap labor for municipal public work projects and private individuals. However, with an increase in demand for penal labor on government-owned farms, the Derg dismantled the tradition of providing inmate labor for private individuals. During the Derg regime, a large number of political detainees were held in a prison some of whom were executed and buried inside the prison premises. “Prisons will become schools and hospitals” was the motto of the regime meant to equip prisoners to lead an honest and industrious life upon their release. Finally, the Derg regime experienced intense political turmoil both from the domestic and international events that resulted in the collapse of the regime and the total prison escape of Derg prisoners from Agäw Meder penitentiary in 1991.