“Finlandisation” has become a buzzword and suggested solution to the on-going Ukrainian crisis. However, in Finland, Finlandisation tends to be a pejorative term because of its negative effects on Finnish domestic politics. Negative effects notwithstanding, Finland’s Cold War experience often appears as a success: it preserved its democratic system, prospered economically, and strengthened its international status. This analysis examines the historical evidence of what role Finlandisation—understood as a policy of collaboration and friendship with the greatest potential security threat to a country’s sovereignty and as a political culture related to that policy—played during the Cold War era. Did the strategy of accommodation go too far and was it superfluous to Finland’s survival and success? In this context, the article also discusses the “dangers” of Finlandisation and the gradual end of the policy.