The article critically reexamines the existing Russian literature on the incorporation of Siberia into the Russian empire and focuses on the encounter between Russian travelers and settlers and the indigenous population of Siberia, seeking an explanation of violent aspects of such an encounter. The author places this encounter in a broad context of administration of Siberia in the 16th – 18th centuries, which lacked rationalization, professional personnel, and resources. He notes that for many Russians an expedition to Siberia was a commercial-colonial enterprise. Both Cossack expeditions and local administration were underfinanced. In this situation the Russian settlers and authorities were prone to bribery, embezzlement of iasak (tribute), and abuse of power in provoking violence and retrieving resources from the local tribes. Major sources of profit were the Siberian furs and enslavement of the local population. Apart from structural factors the author reviews the socio-psychological factors, which contributed to a high degree of violence between the Russian travelers and settlers and indigenous population. He states that people of marginal social standing were most likely to participate in expeditions to Siberia. Consequently, they were inclined to deviant behavior and tended to reproduce in reverse violent treatment, which they experienced in homeland, in a new location. The social tradition of Cossack self-rule also contributed to the state of anarchy and arbitrary government of Siberia. Focusing his article on conflicts between the Russians and local population, the author argues for a complex and balanced approach in studies of the Russian penetration into Siberia.