Siberia, stretching from the steppes of Central Asia in the south to the coast of the Arctic Ocean in the north, and from the boundary of Europe in the west to the Pacific Ocean in the east, has always been a land of great cultural, environmental, and economic diversity. Its history is equally complex, spanning vast human migrations, Turkic conquests, tribal conflicts, and eventually Russian hegemony. But, since the Russian conquest of the region concluded in the early seventeenth century, several things have remained nearly constant. Among these, unique to Siberia is the use of its territory to sustain a system of institutional exile, in which hundreds of thousands of people were sent to serve out terms of banishment as punishment for crimes. American explorer George Kennan, whose remarkable study of the exile system will be more carefully scrutinized later, remarked in an 1882 essay that exiles began to be sent to Siberia almost as soon as the Russian Empire acquired it. Its most recent incarnation, the Soviet GULAG (Главное управление исправительно-трудовых лагерей и колоний, or Main Administration of Correctional Labor Camps and Colonies) system, existed in one form or another until at least 1987. The exact number of people banished to Siberia during this 350-year period is probably incalculable. However, given the enormous global changes that occurred over these three and a half centuries, the system surely must have evolved alongside new social developments, technological improvements, and the shifting winds of politics in European Russia. The question of how and why the exile system evolved, examined primarily through the writings of the Archpriest Avvakum, Fyodor Dostoevsky, and Alexandr Solzhenitsyn, will be the focus of this inquiry.