This article assesses former Russian President Dmitry Medvedev’s proposal for a new security system and varying perspectives in the context of this development. US-led unipolarity has been undermined as a gradually more independent ‘Europe’ has weakened transatlantic unity and that of a broader ‘West’. Russia could neither join the North Atlantic Treaty Organization or the European Union (EU), nor assume directorship for security in the former Soviet Union. It has nonetheless increased its ties and influence with the EU, becoming a major trade partner and the biggest supplier of energy resources. A discourse of multipolarity accompanies Russian geopolitical ambitions and incorporates demands for new arrangements that can facilitate reliable cooperation in the security field and beyond. This implies recognising and accommodating Russian interests, which presents challenges to existing organisations. Medvedev’s proposal is viewed differently by political-security sectors in the United States, Germany, France, Poland, Russia and the hybrid EU.