This chapter covers Russian–Ukrainian relations during pre-Soviet times (ninth century CE until about 1921), the Soviet era (1921–1991), and the period between the fall of the Soviet Union and Ukrainian independence in 1991 and the Euromaidan revolution of 2014. The lands that form present-day Ukraine have been inhabited by independent-minded peoples for centuries. Ukrainian identity began to take on a national character in the 1800s, when writers and activists set up a sprawling network of political movements pursuing an independent Ukraine. The Soviet era was marked by periods of intense suffering: the famines of the 1930s and the slaughters of World War II, during which millions of Ukrainians died as a result of both war and policy. After the Soviet Union came undone in 1991, relations between Russia and independent Ukraine gradually soured after the 2004 Orange Revolution and especially the 2014 Euromaidan Revolution. Over the course of this period, a shift away from ethno-nationalism and towards a civic national identity took place in the country, with especially Russian-speaking Ukrainians ‘shedding’ parts of their ‘Russian-ness’.

As the twenty-first century progresses, geopolitical competition and conflict has steadily increased. Although this competition and conflict is still noticeable offline, there is an increasing focus on online priming and mobilisation of global audiences. This chapter details and analyses the nature of geopolitics in the social media age with the case study involving the struggle for influence in Ukraine. Attempts are made to shape and construct the ’reality’ in Ukraine as a means of freeing-up one’s own operational choices while limiting those of the opponent.

The internal aspect of learning is something that the existing literature has not investigated in detail. A range of examples are investigated in this chapter, with the first section addressing Belarusian and Russian learning from the Soviet Union. Then the chapter analyses how Putin learnt from his image failure after the sinking of the Kursk nuclear submarine in the early 2000s. The Kursk sinking led to a significant change in image with Putin becoming a macho-man. The 2009 Moldovan Twitter Revolution led to learning after the protest on the part of the nominally pro-European government and the Orange Revolution and Euromaidan provided learning opportunities for Ukrainian governments. The chapter then addresses sub-optimal legislation in Belarus and Russia and potential learning from the failure. Learning from failure has not been investigated too much in the existing literature and this chapter addresses the issue.

The chapter addresses examples of learning from external failure, firstly ascertaining Chinese learning from the collapse of the Soviet Union. It then addresses case learning from three revolutions: the Orange Revolution and Euromaidan in Ukraine and the Arab Spring from across the North African and Middle East region. The three protests led to learning on the part of Belarus and Russia in particular. The Orange Revolution directly contributed to preventive counter-revolutions in Belarus and Russia. The collapse of authoritarian regimes across the Middle East and North Africa led to rapid learning from Belarus and Russia. The Euromaidan saw clear learning from Belarus and Russia, but also from Moldova. However, evidence of Moldovan learning is limited, and the chapter highlights that external learning is limited regarding Moldova and Ukraine.

The delay of the Association Agreement spurred protests, and violent repression caused them to grow. Yanukovych’s ouster outraged Putin, who again saw a revolution thwart Russia’s position in Ukraine. He saw an irresistible opportunity to respond. Seizing Crimea regained a territory Russia had always wanted; it showed that Russia could defy the West; it boosted Putin’s domestic popularity; and it hamstrung Ukraine’s new government. The conflict then spread to eastern Ukraine, where the shooting down of a passenger aircraft dramatically increased international outrage at Russia’s actions. The West enacted sanctions, while the conflict itself stabilized territorially in the February 2015 Minsk-2 agreement.

The delay of the Association Agreement spurred protests, and violent repression caused them to grow. Yanukovych’s ouster outraged Putin, who again saw a revolution thwart Russia’s position in Ukraine. He saw an irresistible opportunity to respond. Seizing Crimea regained a territory Russia had always wanted; it showed that Russia could defy the West; it boosted Putin’s domestic popularity; and it hamstrung Ukraine’s new government. The conflict then spread to eastern Ukraine, where the shooting down of a passenger aircraft dramatically increased international outrage at Russia’s actions. The West enacted sanctions, while the conflict itself stabilized territorially in the February 2015 Minsk-2 agreement.