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In 1999 Peace Shield 99 (May 1999), Cooperative Partner 99 (June–July 1999), Sea Breeze 99 (July–August 1999), Cossack Express-99 (September 1999), Cossack Steppe-99 and Black Sea Partnership-99 were held, designed to train and equip the Ukrainian military to fight Russia.
 
In 1999 Peace Shield 99 (May 1999), Cooperative Partner 99 (June–July 1999), Sea Breeze 99 (July–August 1999), Cossack Express-99 (September 1999), Cossack Steppe-99 and Black Sea Partnership-99 were held, designed to train and equip the Ukrainian military to fight Russia.
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The decade of 2000 marked the start of Ukraine becoming a ''de facto'' member of NATO. It not only participated in all of the main exercises, but it hosted many. In fact, between 2000 and 2010, Ukraine is ranked in the top six of countries that hosted a NATO or USEUCOM exercise. Ukraine and the Republic of Georgia, who was ranked number seven, were not NATO members. Two non-NATO countries hosted more NATO exercises than 22 of the member nations. Only two things distinguished Ukraine from NATO members — it did not have a financial obligation to contribute to NATO and it was not covered by Article 5. Other than that, Ukraine was operating as a de facto member of NATO by 2010. Project Ukraine was not confined to military cooperation alone. US and [[UK]] [[intelligence organization]]s were actively involved in Ukraine and were coordinating operations and activities with both NATO and EUCOM. The [[CIA]], for example, has intelligence officers assigned to NATO and USEUCOM headquarters. Their job is to brief senior leaders on CIA operations and coordinate activities to ensure no wires get crossed. During the period between 2000 and 2010, the [[US government]], with [[collaboration]] from the UK, was working intently to split Ukraine away from Russia's sphere of influence and capture it for [[the West]].
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In 2000, the United States European Command (USEUCOM) executed its first Military Contact Plan with Ukraine, following the transfer of responsibility for U.S. military engagement in Ukraine from the Joint Staff to EUCOM in late 1998. The 2000 plan was developed collaboratively with the Ukrainian Ministry of Defense and included a variety of military-to-military events, such as planning meetings, medical, legal, and chaplain exchanges, and other cooperative activities. These events were designed to align with specific objectives and priorities identified by both sides.
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In March 2003, Ukraine finalized its 2003 Target Plan within the NATO-Ukraine Action Plan framework. This plan provided for intensified military cooperation, consultations, and preparation for large-scale military exercises, including international ones. These activities were part of a broader effort to align Ukraine’s military standards and procedures with those of NATO, as well as to test military equipment and armaments
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in a multinational context.
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In 2004, Ukraine participated in several significant military exercises with NATO and U.S. European Command (USEUCOM), reflecting its growing partnership with the Alliance and Western militaries following the 2002 NATO-Ukraine Action Plan.
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Throughout 2005, NATO and Ukraine developed practical projects aimed at addressing Ukraine's [[national security]] and defense needs. These included the launch of PfP trust funds to assist with the destruction of excess munitions and the retraining and resettlement of redundant military personnel. Additionally, there was the launch of a project to assist with the training of [[civilian]] personnel for Ukraine's security and defense structures.
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The first Rapid Trident exercise in Ukraine took place in 2005 at the Yavoriv training ground as part of the Partnership for Peace program, marking the beginning of this recurring multinational exercise.
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In 2006 a broader push for NATO integration followed the [[Orange Revolution]] (2004).
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In 2007, NATO and Ukraine conducted a notable command post exercise in [[Sevastopol]] and maintained a structured program of military cooperation under the NATO-Ukraine Military Work Plan and Annual Target Plan. The chiefs of defense from NATO and Ukraine met in May 2007 to assess progress under the NATO-Ukraine Military Work Plan for that year. They tasked their military representatives to begin preparations for the next cycle of cooperation, indicating ongoing planning and execution of joint activities. The NATO-Ukraine Annual Target Plan (ATP) for 2007 outlined practical steps for cooperation in [[political]], [[military]], and security spheres, including exercises and advisory activities to improve Ukraine’s Euro-Atlantic integration. While the ATP itself is a planning document, it confirms that military exercises and collaborative activities were a significant part of the 2007 agenda.
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The NATO-Ukraine Annual Target Plan for 2008 formalized cooperation, including joint exercises, training, and seminars . Ukraine’s participation in multinational exercises was part of its broader Euro-Atlantic integration efforts, as reaffirmed at the 2008 [[NATO Bucharest Summit]]. While Sea Breeze and Immediate Response were the most prominent multinational exercises involving Ukraine in 2008, other smaller joint training events and seminars were also conducted under the NATO-Ukraine partnership framework.
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These exercises occurred amid Ukraine’s push for a NATO Membership Action Plan (MAP) at the April [[2008 Bucharest Summit]]. While NATO declined to grant MAP due to opposition from some members (e.g., [[Germany]] and [[France]]), it affirmed Ukraine’s future membership prospects, stating it "will become a member of NATO" eventually. [[Russia]] strongly opposed these developments, escalating tensions that later influenced its [[2014 annexation of Crimea]].
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The exercises in 2009 were central to strengthening Ukraine's [[military]] cooperation with NATO and the U.S., laying the groundwork for deeper defense ties in subsequent years These exercises were part of Ukraine’s NATO Partnership for Peace (PfP) program, which sought closer military cooperation without full membership. Russia strongly criticized these drills, particularly Sea Breeze, as encroaching on its [[sphere of influence]]. The training laid groundwork for future cooperation, especially after Russia’s 2014 annexation of Crimea, when Ukraine intensified NATO-linked exercises.
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These exercises also were part of the broader NATO-Ukraine cooperation, as outlined in the NATO-Ukraine Annual Target Plan for 2009, which emphasized joint training, equipment modernization, and increasing interoperability. USEUCOM (United States European Command) regularly supported and participated in these exercises, underscoring the U.S. commitment to [[European]] security and partnership with Ukraine.
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2010 was part of Ukraine’s pro-NATO phase under President [[Viktor Yanukovych]], who initially continued military cooperation, despite later rejecting NATO membership (2010–2014). The Ukrainian Cabinet of Ministers approved an action plan in June 2010 for annual cooperation with NATO, which included participation in NATO-led peacekeeping missions, joint exercises, and training of Ukrainian troops within NATO structures. Ukraine participated in NATO's Operation Active Endeavour, a counter-terrorist maritime surveillance operation in the [[Mediterranean Sea]]. Ukraine deployed ships to support this operation six times between 2007 and 2010, including in 2010. The State Partnership Program (SPP) between Ukraine and the U.S. National Guard (California) continued, including joint training events.
    
{{Anchor|NATO aggression against Serbia}}
 
{{Anchor|NATO aggression against Serbia}}
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