President Barack Obama’s administration has been working behind the scenes for months to forge a new working relationship with Russia, despite the fact that Russian President Vladimir Putin has shown little interest in repairing relations with Washington or halting his aggression in neighboring Ukraine.

This month, Obama’s National Security Council finished an extensive and comprehensive review of U.S policy toward Russia that included dozens of meetings and input from the State Department, Defense Department and several other agencies, according to three senior administration officials. At the end of the sometimes-contentious process, Obama made a decision to continue to look for ways to work with Russia on a host of bilateral and international issues while also offering Putin a way out of the stalemate over the crisis in Ukraine.

“I don’t think that anybody at this point is under the impression that a wholesale reset of our relationship is possible at this time, but we might as well test out what they are actually willing to do,” a senior administration official told me. “Our theory of this all along has been, let’s see what’s there. Regardless of the likelihood of success.”

Leading the charge has been Secretary of State John Kerry. This fall, Kerry even proposed going to Moscow and meeting with Putin directly. The negotiations over Kerry’s trip got to the point of scheduling, but ultimately were scuttled because there was little prospect of demonstrable progress.

In a separate attempt at outreach, the White House turned to an old friend of Putin’s for help. The White House called on former Secretary of State Henry Kissinger to discuss having him call Putin directly, according to two officials. It’s unclear whether Kissinger actually made the call. The White House and Kissinger both refused to comment for this column.

Kerry has been the point man on dealing with Russia because his close relationship with Russian Foreign Minister Sergei Lavrov represents the last remaining functional diplomatic channel between Washington and Moscow. They meet often, often without any staff members present, and talk on the phone regularly. Obama and Putin, on the other hand, are known to have an intense dislike for each other and very rarely speak.

In several conversations with Lavrov, Kerry has floated an offer to Russia that would pave the way for a partial release of some of the most onerous economic sanctions. Kerry’s conditions included Russia adhering to September’s Minsk agreement and ceasing direct military support for the Ukrainian separatists. The issue of Crimea would be set aside for the time being, and some of the initial sanctions that were put in place after Crimea’s annexation would be kept in place.

“We are willing to isolate the issues of Donetsk and Luhansk from the issue of Crimea,” another senior administration official told me, naming two regions in Eastern Ukraine under separatist control. “If there was a settlement on Donetsk and Luhansk, there could be a removal of some sanctions while maintaining sanctions with regard to Crimea. That represents a way forward for Putin.”

Meanwhile, Kerry has been proposing increased U.S.-Russian cooperation on a wide range of international issues. Earlier this month, he invited Lavrov to a last-minute diplomatic confab in Rome to discuss the the Israeli-Palestinian conflict.

After one meeting with Lavrov in Paris in October, Kerry announced that he had discussed potential U.S.-Russian cooperation on Afghanistan, Iran, North Korea, Syria and Yemen. But the apparent warming was overshadowed by Lavrov’s quick denial of Kerry’s claim that Russia had agreed to assist in the U.S.-led coalition against Islamic State in Iraq.

Kerry has seemed more enthusiastic about mending ties with Russia than Obama himself. After the president gave a blistering critique of Russian behavior in a major United Nations speech, saying that “Russian aggression in Europe recalls the days when large nations trampled small ones in pursuit of territorial ambition,” Kerry urged Lavrov to ignore his boss’s remarks, according to Lavrov. “Kerry said we have so many serious things to discuss that of course that was unfortunate, let’s not focus on that,” Lavrov told Russian reporters.

State Department officials insist that Kerry is clear-eyed about the challenges of trying to work with Russia, but that he believes there is no other responsible option than to see what can be accomplished.

“Secretary Kerry is not advocating internally or with Russia for a reset in the relationship, and in fact in meetings he has taken a strong and at times skeptical stance,” one senior State Department official told me. “As the nation’s chief diplomat he is simply always exploring ways to make relationships more productive.”

There is also a belief among many both inside the State Department and the White House that sanctions are working. The Russian economy is tanking, albeit due largely to collapsing oil prices and not targeted punishments. One senior administration official argued that absent the sanctions, Putin might have been even more aggressive in Ukraine. Moreover, this official said, the sanctions need time to work and might yet prove to have greater effect on Putin’s decision-making in the months ahead: “We’ll see how they feel as their economy continues to deteriorate and the Ukrainian economy refuses to collapse.”

If the Russians are getting ready to cave, they aren’t showing it. Putin remains defiant and Russian military assistance to the Ukrainian rebels continues. The Russian leadership has been rejecting Kerry’s overtures both in public and private. Diplomatic sources said that Lavrov has refused to even discuss Kerry’s conditions for partial easing of sanctions. And Putin has made a hobby of bashing the U.S. in public remarks.

To many of the administration’s critics, especially Republicans on Capitol Hill, pursuing engagement with Moscow is based on naivety and wishful thinking.

“It’s a strategy worthy in the finest tradition of Neville Chamberlain,” incoming Senate Armed Services Chairman John McCain told me. “I think the Russians are doing fine. Meanwhile, what price has Vladimir Putin paid? Very little.”

The legislative branch has also been active on Russia this year, but its efforts run counter to the administration’s policy and sometimes have the indirect effect of putting more roadblocks in front of the Obama-Kerry push to find a way forward.

On Dec. 18, Obama reluctantly signed a bill authorizing new Russia sanctions and military aid to Ukraine that was overwhelmingly passed by Congress. Afterward, the White House awkwardly said that the legislation did not signify any change in policy.

And this week, the State Department sanctioned four more Russian officials, but not over Ukraine. The officials were added to a list of human rights violators under the Sergei Magnitsky Act of 2012, named after the anti-corruption lawyer who died in a Russian prison. In response, the Russian foreign ministry issued a statement saying that the Magnitsky Act sanctions “place in question the prospects for bilateral cooperation in resolving the situation surrounding the Iranian nuclear program, the Syrian crisis, and other acute international issues.”

These latest punishments show that it may be impossible to de-link the problems in the bilateral relationship from the opportunities, as the Obama administration wants to do. They also show that there will always be chances for those in Washington and Moscow who want to stoke the tensions to do so, jeopardizing any progress.

Some experts believe that any plan to warm U.S.-Russian relations is unlikely to succeed because it doesn’t have the full support of either president.

“It’s very clear that between the Putin Kremlin and the Obama White House there is a very bad chemistry. Its not a question of simply distrust, it’s a question of intense dislike between the two leaders,” said Dimitri Simes, president of the Center for the National Interest.

Also, some experts feel, placing the diplomacy in the Kerry-Lavrov channel dooms its outcome, because the Russians know that Kerry himself has no power to make major decisions and Lavrov has to be careful not to be seen as cozying up to the U.S.

“The more Kerry creates a perception he has a special relationship with Lavrov, the more he puts Lavrov in a difficult position with officials in his own capital, starting with Putin,” said Simes. “It’s clear that when Kerry deals with Lavrov and hopes that because they have overlapping interests, that would allow cooperation where useful, that is not a model of relationship that Putin is prepared to accept.”

Obama has made it clear that in his last two years in office he is prepared to make big moves on foreign policy even if they face political or legislative opposition, such as normalizing relations with Cuba or pursuing a nuclear deal with Iran. But when it comes to Russia, he is unwilling to place his own credibility behind any outreach to his nemesis Putin.

The administration’s cautious engagement with Moscow is logical: Why not seek a balance in a complicated and important bilateral relationship? But by choosing a middle ground between conciliation and confrontation — not being generous enough to entice Russia’s cooperation yet not being tough enough to stop Putin’s aggression in Eastern Europe — Obama’s policy risks failing on both fronts.