The Kaliningrad issue has always been part of several contexts of Lithuanian foreign policy and security assurance. That is why it is significant to look at what relationship models Lithuania has tried to implement with Kaliningrad and what opportunities and threats it has created for Lithuania. This article analyses the Kaliningrad factor, which became apparent during Vladimir Putin’s rule, in Russia’s relations with Lithuania, the EU, and NATO, and assesses the aspects of both “hard” and “soft” security. We argue that it is important to consider what Kaliningrad Oblast means to Russia, what role it plays in its foreign policy, how it is changing and what the dynamics of the EU and Lithuania’s relations with Kaliningrad has recently been, and what the possible and desirable scenarios of Lithuania’s cooperation with Kaliningrad could be.