The Soviet collapse in 1991 not only meant the removal of the multinational Soviet superstructure, it also opened up the Russian territory to Western - and more specifically Norwegian - impulses to a degree that was unprecedented and that was not to be repeated. Norwegian entrepreneurs and political actors attempted to give the post-Soviet transition direction, both for altruistic reasons as well as for profit. However, already in the mid-1990s, the first signs of Russian skepticism to Western values became apparent. The conviction that Russia needed to find its own path and deviate from what was deemed appropriate in Berlin, Washington and London was elevated from a political sub-current to official policy during the mid-2000s. In a historical perspective, the chapter argues, the Norwegian-Russian relationship was much closer to its normalcy in 2014 than in 1991. This, of course, has implications for Norwegian policy making in relation to Russia.