This morning, Moscow woke up to the news that the U.S. had hit an air base in Homs, Syria, in retaliation for Bashar al-Assad’s use of chemical weapons in Idlib province. This was accompanied by the usual protestations from the Kremlin, which complained that the U.S. had bypassed international law “under an invented pretext” and violated Syria’s sovereignty.

Maria Zakharova, the spokeswoman for the Russian Foreign Ministry, complained that the Trump administration made no efforts to verify who was behind the sarin gas attack and that, in striking Syria, the U.S. was attacking a country that has always fought “global terror” in order “to prove itself.” The Defense Ministry announced that the 2015 memorandum on deconfliction—worked out between Washington and Moscow to avoid air collisions in their anti-ISIS operations—was now moot, and Dmitry Peskov, Vladimir Putin’s spokesman, warned that the chances of collision were now much higher. Russian TV compared the bombings in Homs to the American bombings of Yugoslavia, Iraq, and Libya. And Margarita Simonyan, the head of the Russian propaganda outlet RT, asked if anyone cared to remember that 100 years ago to the day, America entered World War I.

Of course the Kremlin was upset, and of course it had to make a very convincing and angry show of condemning the operation. The Trump administration, for which it had such high hopes, was now like every American administration in recent memory: using the guise of human rights to circumvent the UN and intervene against what Russia considers legitimate governments—sometimes toppling them—and sowing chaos. Moreover, it did this in a country where Russia has a large military presence, which the United States seemed to completely disregard.

Yet it all felt kind of weak, a flaccid replica of Washington and Moscow’s usual sparring over the pockmarked and desolate landscape of concrete skeletons once known as Syria. Despite its morning protestations, the Russian Defense Ministry got out of the way after the Pentagon used the deconfliction channels to warn Moscow of the coming attack. The day before Trump rushed to action and Peskov was forced to repeat Russia’s standard tropes about Syria’s national sovereignty and international law and going through the UN, Putin’s spokesman seemed to hint at Moscow’s fatigue with a client gone rogue. Moscow’s support for Assad, Peskov said, “is not unconditional,” before retreating behind platitudes about the need for a thorough—read: long—investigation into the chemical attack and assurances that Moscow did not have full control over Assad.

Even Moscow’s defense of Assad—that his air force hadn’t dropped sarin gas on civilians but had simply bombed a rebel warehouse containing sarin—felt weak. By contrast, when Assad gassed civilians in the Damascus suburb of Ghouta in August 2013, Moscow claimed that it had been a false flag operation by rebels intent on drawing the United States into the fight and onto their side.

When you become a guarantor, at some point the bill comes due.

The response today is understandable. Moscow had already given Assad three and a half years of breathing room after proposing, in 2013, that he hand over his chemical arsenal over to an international coalition. It was a masterful way to allow everyone involved to save face. Obama wouldn’t have to do what he was loathe to do—intervene in a messy civil war—but striking the deal would allow him to say that he had eliminated the aspect of the war that was most gruesome and most obviously violated international law. The deal allowed Assad to avoid being pounded by the American air force while using his own to continue to kill civilians by every other imaginable means. And most importantly from Moscow’s point of view, it allowed Russia to show itself in the light it had long wanted to be seen on the global stage: the one responsible, adult actor who wasn’t, like the U.S., rushing to pull the trigger, but was instead trying to reach sensible, peaceful resolutions to complex problems. With Russia long the spoiler in the UN Security Council and the international arena, the chemical-weapons deal allowed the country to establish itself as an indispensable arbiter of geopolitics.

In effect, Putin drew his own red line, right over Obama’s. Putin gave Assad a free pass to use any means to fight his people, anything save for chemical weapons. Moscow is a stickler for the letter of international law, and in 2013, it quickly organized a unanimous vote in the UN Security Council and a broad international coalition to oversee the destruction of Assad’s chemical arsenal at sea. But despite the pointedly international nature of the operation, Moscow had essentially acted as Assad’s guarantor, with Putin having to ensure that Assad would no longer use chemical weapons. But three years later, Assad has clearly been emboldened by Russia’s military help and diplomatic cover for brutally reconquering Aleppo and other territory. If Assad can bomb aid convoys, starve cities into submission, if he can use mass torture and barrel bombs and even chlorine gas because it wasn’t covered in the 2013 deal, why not push the envelope a little further and use a little sarin gas he’s squirreled away or redeveloped or bought somewhere?

Now, there is little Moscow can do to save face. It gathered an international coalition to dispose of Assad’s chemical weapons, and made political hay out of their destruction, only to have Assad make Moscow’s effort look either less than thorough, or gruesomely insincere. Either way, Russia doesn’t look like much of a guarantor.

At the same time, though, it can’t just allow Washington to unilaterally violate the ideas of national sovereignty it has spent years, treasure, and Russian blood defending in Syria. It can’t allow Washington to so obviously disregard not just Putin’s opinion, but the Russian military. And so Moscow has to condemn the American strikes strongly enough to retain its position as a defender of the UN Security Council and international law, strongly enough to maintain its stature as a global military power—but not so strongly that it appears to condone not just the gassing of children but, more importantly for Moscow, the violation of international law on chemical weapons, a law that it helped to enforce in 2013.

Putin is brilliant at finding quick maneuvers that advance his agenda in the moment. But time doesn’t always work in his favor.

The problem for Moscow is that this was all painfully predictable. In helping Obama kick the chemical weapons can down the road, there was only so long Putin could continue to embolden Assad before Assad would go too far, at which point there would be no more forgiveness from the very international community Moscow had helped to galvanize.

And this is perhaps the ultimate lesson for Americans who fetishize Putin as the ultimate, perfect villain, who outfoxes the hemming, hawing United States at every turn in Syria. Putin is brilliant at finding quick maneuvers that advance his agenda in the moment. He too kicks the can down the road, repeatedly. But that road is not endless, and time doesn’t always work in his favor. Or, put another way, when you become a guarantor, at some point the bill comes due.