Russian President Vladimir Putin prides himself on successfully pursuing good relations with governments and other actors even when they are simultaneously strongly opposed to each other. Up until recently, he has done this successfully along multiple dimensions in Syria alone.

Despite the bitter animosity between Israel and Iran, Moscow has been able to work closely with both governments. Similarly, Moscow has been able to balance between the Syrian Kurds on the one hand and Turkey on the other. Putin has even been able to balance between Turkey and the Assad regime where they oppose each other in Idlib and elsewhere in northwestern Syria. But this last balancing act has now broken down spectacularly as the conflict between Turkish and Syrian forces in the Idlib region has escalated.

Putin very much wants to maintain good relations with both Turkish President Recep Tayyip Erdogan and Syrian leader Bashar al-Assad. The problem, though, is that these two leaders are strongly opposed to each other. Assad has consistently proclaimed his intention to retake every inch of Syria from his opponents, including the Turkish-backed Islamists who have holed up in Idlib as they have lost ground elsewhere. For Erdogan, though, losing Idlib to Assad would result in yet another massive wave of Syrian refugees fleeing north to Turkey which is having difficulty accommodating the ones who have previously fled there.

The success of Putin’s balancing between opposing sides simultaneously depends on the parties involved not being willing or able to pursue all-out conflict with each other. Moscow’s judiciously providing assistance to both sides is designed to reinforce this perception — as well as to make money for Russia by selling arms and obtaining other economic benefits from both sides. Each opposing side, of course, is not happy about Moscow also supporting its adversary. But the logic of the situation, as Moscow sees it, is that neither can afford to cut or curtail ties to Moscow over this for fear that Russia will help its adversary even more. Instead, Moscow hopes that its willingness to support opposing sides will encourage competition for Moscow’s favor through each side offering it favors and concessions. Most of the time, Putin’s approach has worked.

And from Moscow’s viewpoint, it should work now too. On the one hand, Assad owes his very survival to the Russian military intervention in Syria that began in 2015. The Assad regime was under serious threat up until then despite the massive assistance he was receiving from Iran, Hezbollah, and other Shi’a militias. According to this logic, Assad should not do anything that risks trying Moscow’s patience.

Similarly, Erdogan’s increasing animosity toward America and Europe (which Putin has encouraged) should result in making Turkey more dependent on Russia. Putin has already done much to accommodate Turkish interests in northern Syria. And with the Turkish economy dependent on Russian gas supplies as well as trade, Erdogan too should not risk trying Putin’s patience. The economic sanctions that Russia imposed on Turkey after Turkish forces downed a Russian military aircraft in late 2015 but then lifted as Russian-Turkish relations improved should serve as a warning to Erdogan.

Unfortunately for Putin, neither Assad nor Erdogan appears to accept his logic over how it is rational to behave. The very fact that Russian intervention has saved the Assad regime and re-established its rule over much of Syria has put Assad in a much stronger position to try to retake Idlib than he would have been otherwise.

Similarly, instead of seeing Turkey as needing Russia more than Russia needs Turkey (as Putin appears to believe), Erdogan sees Russia as needing Turkey more. Erdogan’s recent visit to Ukraine and statement of support for it as well as his newly rediscovered enthusiasm for NATO indicates that Erdogan believes that Putin has something to lose by displeasing Erdogan in Syria.

Further, since both Erdogan and Assad believe that they each have vital interests at stake in Idlib, neither is willing to back down despite a genuine Russian desire for a solution that accommodates them both. Instead of maintaining good relations with the two opposing parties as it has in the past, Moscow now faces the prospect of losing influence with one of the antagonists — or even both. Reports indicate that while Turkey is angry because of what it sees as Russian air support for Syrian attacks against Turkish forces, Syria is also angry because of what it sees as insufficient Russian support.

Moscow really cannot afford to let Turkey defeat Syrian forces in northwestern Syria, because this risks stimulating opposition to it elsewhere in Syria. But helping the Assad regime fight off Turkish forces in northwestern Syria could involve Russia in a much bigger and longer conflict than Putin wants. Even if successful against Turkey, the damage to Russian-Turkish relations could this time be irreparable. Putin’s balancing act between Erdogan and Assad may no longer be sustainable.