The article explores the EU diplomacy toward Russia since Josep Borrell took office as EU High Representative for Foreign Affairs and Security Policy. The approach adopted by the European External Action Service (EEAS) in a time of crisis is examined, in the context of the rapidly changing international security environment and the unprecedentedly low level of engagement between Russia and the EU. The research featured the EEAS official documents, press releases, and Josep Borrell’s statements issued from late 2019 to early 2022. The analysis revealed some of Borrell’s ideas about the international role of the EU, his image of Russia and his suggestions on the EU’s course of action towards Russia. The author believes that Borrell’s approach clearly failed the reality test. The EU diplomacy demonstrated its inability to adjust to the escalating tensions and the major changes in the bilateral relations, as well as in Russia itself. As a result, the European strategy has proven ineffective and unable to address adequately the challenges it faces.