Next month, Japanese Prime Minister Shinzo Abe will welcome Russian President Vladimir Putin to Japan for a much-anticipated summit. Since taking office in late 2012, Abe has expended considerable effort to improve Japan’s strained relationship with Russia. Abe and Putin have met on numerous occasions on the sidelines of international meetings at the former’s bidding. Abe even boldly traveled to Russia in February 2014 to meet Putin in Sochi for the Winter Olympic games while most of his G-7 colleagues stayed away. He returned to Sochi this past May and then, most recently, met with Putin at an Eastern Economic Forum in Vladivostok in September.

Abe has also promised a suite of economic incentives—an “eight-point plan”—to enhance Japan’s economic relationship with Russia. Moreover, he has tasked his confidante, Hiroshige Seko, the Minister of Economy, Trade, and Industry, with a new portfolio focused on economic cooperation with Moscow. The plan covers several areas, including energy security, Japanese investment in Russia’s Far East, and the improvement of exchanges between small to medium-sized companies in the two countries.

What is Abe angling for in his courtship of Russia? A number of factors drive Tokyo’s push to normalize relations with Moscow—including the desire to strengthen ties on energy security and hedge against Chinese power in the region. But Abe’s main political motivation remains his desire to achieve a diplomatic breakthrough with Putin on the decades-old territorial dispute over the Southern Kuril islands (called the Northern Territories in Japan). The Russians have administered the four islands (Etorofu, Kunashiri, Habomai, and Shikotan) since the Soviet Union seized them at the end of World War II. Every Japanese Prime Minister has felt pressure to make progress on the unresolved territorial row, and now Abe is trying again.

The Japanese government has long insisted that all four islets be returned to Japan, despite Moscow’s apparent lack of any real intention to acquiesce to such demands. The only framework for a deal amenable to both governments was the 1956 Japan-Soviet Declaration, which outlined the return of the two smaller islands (Shikotan and Habomai) in exchange for a peace treaty between both sides to formally end diplomatic hostilities begun in World War II. The issue of the sovereignty of Etorofu and Kunashiri was effectively shelved by that proposed deal. However, the pact was scuttled due to pressure from the U.S. government, which feared that the Japanese might grow closer to the Soviet Union in its wake.

There have been numerous negotiations and proposal since 1956, but no real indication that Russia is willing to alter its position. And despite Putin’s reference to the need for a hikiwake—or “draw”—to end the territorial row, it remains unlikely that the Kremlin envisions making any concessions beyond the 1956 deal. Indeed, while Putin allows the Japanese to hope, other Russian officials and politicians have said outright that the islands will not be returned. Indeed, Russian Foreign Minister Sergei Lavrov has repeatedly insisted that the islands will remain under Russian control. And during a recent trip to Japan, Valentina Matviyenko, the head of Russia’s upper chamber of parliament, also stressed: “Russia’s sovereignty over the islands is certified by a certain international document. Russia cannot just give up that sovereignty.”

This has not stopped Japan’s leaders from floating a range of proposals and compromises. The most commonly discussed resolutions now revolve around the return of Shikotan and Habomai—only 7 percent of the total territory of the Southern Kurils—and some form of joint administration or development of the larger islands.

Thus, Abe feels considerable pressure to conclude this dispute, and has staked a large amount of political capital on achieving a grand bargain with Putin. To that end, he met with the Russian President on the sidelines of the APEC summit in Peru this past weekend, but the far more important meeting will be the December summit in Yamaguchi, the Prime Minister’s home prefecture. If Abe does not achieve significant progress at that meeting, the pressure on him will increase.

Abe’s diplomatic outreach to Putin has come under scrutiny from the Obama Administration, which is displeased that he has refused to join the G7 nations in isolating Moscow on account of its annexation of Crimea and continued interference in Eastern Ukraine. Japan continues to walk a very fine line as it balances diplomatic overtures to Moscow with its attempt to maintain solidarity with the G7 on Ukraine and Moscow’s more muscular foreign security policy. Adding to the complexities of this issue, many in Tokyo see Russia’s annexation of Crimea as a potential precedent for China, which has ambitions to alter the status quo of its territorial disputes by the use of force in the East and South China Seas.

However, Abe has strategically timed his summit during the lame-duck period of the U.S. election year and has calculated that Putin’s visit to Japan may slip through without the usual scrutiny from Washington. He seems to have made the right call on this point, and this month’s surprising election of Donald Trump as the next U.S. President is likely to provide further cover for his meeting with Putin. Trump stated during his campaign that he wants to improve relations with Russia. However, it is unclear how this will translate into policy in the coming months, and Tokyo should be careful not to interpret Trump’s victory as carte blanche to engage with Russia on any terms. Moreover, even with what is likely to be a more understanding administration in Washington, Abe is unlikely to secure a grand bargain from Putin on the islands any time soon.