Abstract: Prime Minister Abe Shinzō’s anticipated trip to St Petersburg and Moscow at the end of May 2018 represents the culmination of his “new approach” to Russia. Unveiled two years earlier, this policy seeks to achieve a breakthrough in the countries’ long-standing territorial dispute by reducing Japan’s initial demands and offering incentives in the form of enhanced political and economic engagement. Having stuck resolutely with this policy despite criticism from the West, Abe now needs it to deliver, not least to boost his flagging approval ratings. This article highlights exactly what the Japanese leader hopes to achieve and assesses his prospects of success. Particular emphasis is placed on the proposed joint economic activities on the disputed islands and the specific legal obstacles that need to be overcome.