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[[File:Ivan the Terrible and Harsey.jpg|thumbnail|400px|left|Figure 1. Ivan helped create among the first secret police organizations in Russia.]]

Ivan IV Vasilyevich (sometimes better known as Ivan the Terrible or Ivan the Formidable) may have established one of the first espionage services in Russia in the 16th century. Ivan was one of the first monarchs to create a very centralized Russian state. Before his time, Russian nobles often held great power and influence and would often oppose the actions of the tsar. He created an organization called the Oprichnik, who were a group of operatives loyal to the tsar and effectively became Russia's first state police and spy service.

The Okhrana were unprepared for the 1905 Russian Revolution, where their actions may have even made events even worse for the regime. Often, agents worked in small groups and did not coordinate activities. This meant information was not well shared and it was not able to properly identify a large, national-level movement had been launched. Reforms after 1905 included creating spy stations in various cities in Russia that would enable the Okhrana, which was within the wider policing structure of the Russian state, to try to centralize information and be better prepared to root out conspiracies. One role the Okhrana became involved with was promoting counter groups to offset revolutionary groups. In fact, the Bolsheviks were, initially at least, seen as a counterweight to other leftist violent groups that were often seen as a greater threat to the state. Nevertheless, prominent members, who later became well known communists, such as Stalin, were detained by the Okhrana at various times for subversive activity or even simple criminal activity (Figure 2). However, Lenin was opposed to many of the other opposition parties, leading Okhrana to silently support him as a counterweight. This, overall, helped make Okhrana less able to see the rise of the Bolsheviks as a major threat. In fact, in the events of 1917 that led to the overthrow of the Russian monarch, Okhrana's failure was to not monitor the military, where the Bolsheviks and other revolutionaries had many sympathizers, as it saw military espionage as not honorable. Despite its shortcomings, the succeeding Soviet agencies initially modeled themselves after the Okhrana, specifically the Cheka which became the first secret police after the fall of the Russian Empire. The use of local spy bases and networks that were better coordinated did serve as a useful model for later secret police.<ref>For more on the failure of the Russian spying services to stop the 1917 overthrow, see: Lee, Stephen J. 2006. <i>Russia and the USSR, 1855-1991: Autocracy and Dictatorship</i>. Questions and Analysis in History. London ; New York: Routledge, pg. 73.</ref>

[[File:Nevertheless, prominent members, who later became well known communists, such as Stalin's Mug Shot.jpg|thumbnail|, were detained by the Okhrana at various times for subversive activity or even simple criminal activity (Figure 2). Mug shot However, Lenin was opposed to many of Stalin after he had been detained by the other opposition parties, leading Okhrana to silently support him as a counterweight. This, overall, helped make Okhranaless able to see the rise of the Bolsheviks as a major threat. Stalin In fact, in the events of 1917 that led to the overthrow of the Russian monarch, Okhrana's failure was sentenced to exile not monitor the military, where the Bolsheviks and other revolutionaries had many sympathizers, as it saw military espionage as not honorable. Despite its shortcomings, the succeeding Soviet agencies initially modeled themselves after the Okhrana, specifically the Cheka which became the first secret police after the fall of the Russian Empire. The use of local spy bases and networks that were better coordinated did serve as a useful model for later secret police.<ref>For more on the failure of the Russian spying services to Vologda stop the 1917 overthrow, see: Lee, Stephen J. 2006. <i>Russia and the USSR, 1855-1991: Autocracy and Dictatorship</i>. Questions and Analysis in 1911 but later escaped in 1912History. London ; New York: Routledge, pg. 73.]]</ref>

Similar to other espionage agencies, the Russian experience developed from domestic espionage conducted to protect the expanding and increasingly centralized state in the 16th century. Domestic and foreign spying were often kept in the same organization, which continued throughout the Soviet Union period; however, now there were other organizations that also carried out policing and spying activities.  Nevertheless, the structures increasingly became complex by the late 19th century and early 20th century, as Russia and then the Soviet Union found itself protecting a large frontier and spending a lot of effort in domestic policing of its population through counterintelligence and repression of violent groups. With increased internal violence, spying agencies resorted to more violent measures to carry out activities, including heavy use of torture. This likely helped to fuel animosity with the fall of Russia and eventually the fall of the Soviet Union, in both cases where the policing agencies were dismantled, in part due to their violent reputations. Nevertheless, the lessons learned by the Soviets did make them highly effective in using Communist sympathizers to help them steal major secrets and carry out other espionage before and during the Cold War. Espionage in Russia improved through lessons learned from a long history that started in the 16th century.