This chapter examines President Barack Obama’s Russia policy in his second term in office, arguing that the policy approach has consistently reflected both doctrine and legacy. When Barack Obama began his first presidential term in 2008, he was to preside over an attempt to reset a relationship with Russia that was then experiencing its worst decline since the end of the Cold War. Near to the end of his second term, however, relations with Russia were at an even lower point than when Obama first became President. Indeed, even by the beginning of his second term, hopes for the reset had dwindled. It was in this context that the Obama administration settled on what is best described as a ‘damage limitation policy’, recognising the impossibility of positively influencing Putin’s foreign policy, seeking instead to do the least amount of damage in the hope of keeping the doors open for a more productive relationship with Putin’s successor.