On December 10, Ukraine conducted a drone attack on the Dashan, a tanker associated with Russia's clandestine fleet, as part of a broader maritime campaign initiated in late November. This campaign targets a network of vessels transporting sanctioned oil, which is vital for sustaining the Russian economy. Reports indicate that the CIA has been involved in training Ukrainian forces to effectively strike key components of Russia's oil infrastructure, despite fluctuations in U.S. support under the Trump administration.

The CIA's assistance reportedly included intelligence on targeting oil refineries deep within Russia, which was approved under the Trump administration amid rising frustrations over Russia's military actions in Ukraine. The U.S. has historically shared intelligence with Ukraine to aid in military operations, including warnings about incoming Russian attacks. However, military aid was temporarily frozen in March due to internal skepticism within the White House, led by Vice President JD Vance and others.

Despite these challenges, a coordinated effort between the CIA and U.S. military has focused on crippling Russia's oil refining capabilities, achieving significant reductions in output and economic impact. The strikes have reportedly cost the Russian economy approximately $85 million per day, highlighting the strategic importance of energy resources in the conflict.

The evolving dynamics of U.S.-Ukrainian relations have been marked by inconsistent decision-making within the Trump administration, which has been criticized for its approach to negotiations with Russia. The complexities of these interactions, including personal rapport between leaders, have influenced diplomatic efforts, underscoring the intricate relationship between military strategy and political negotiations in the context of the ongoing war.