The authors of the article analyse how the policy of the Russian Federation towards Kaliningrad Oblast could influence main national interests of the Lithuanian Republic - the integration into the EU and NATO. Thus two main problems are discussed in the article: first, how Russia seeks to use the problem of military transit to/from Kaliningrad Oblast, stopping Lithuania's Euro-Atlantic integration; second, the interaction of what factors within the context of the EU enlargement could influence decisions on visa and civic transit issues. It is emphasized, that the EU enlargement creates a pressing need for indepth modernisation of the Oblast (for the implementation of which Russia is not ready and lacks capacity). Neither Russia nor the EU (including candidate countries) is interested in the potential worsening of the socio-economic situation in Kaliningrad region. Due to this reason, successful crisis prevention should be an important interest for all regional actors. Nevertheless, analysis of their positions reveals that there is a lack of strong political determination to decide the Kaliningrad issue substantially (by resorting to unconventional tools, breaking the status quo), as the problem of successful adaptation of the oblast (together with the relevant values) is not placed high on the regional actors’ agenda. The analysis of Russian military transit from/to Kaliningrad Oblast indicates that the Kremlin was seeking political agreement on military transit in the hope of holding Lithuania in its sphere of influence. The presumption is made that Russia could again try to legitimate the military transit through the territory of Lithuania even if Lithuania is invited to join Euro- Atlantic structures.