U.S. President Donald Trump spent most of the past week desperately trying to spin his controversial summit with Vladimir Putin as a breakthrough, despite widespread impressions of near-total capitulation on the question of Russian interference in the 2016 election.

“The Summit with Russia was a great success, except with the real enemy of the people, the Fake News Media,” the president insisted in a typically bristling tweet on Thursday.

As Trump struggles to cast his odd-couple bond with Putin in a positive light, it’s worth recalling he’s not the only major world leader with a perceived “Russia problem.” Pope Francis has one too, and although the pontiff embodies a wildly different outlook and agenda from the U.S. leader, we may be on the brink of a major turning point in his ties to Russia as well.

From the beginning of his papacy in July 2013, Francis’s tenure seemed full of promise on the ecumenical front, including with Russia. Finally, the Catholic Church had a leader from the developing world who didn’t carry the baggage of centuries of rivalries between East and West in Europe, and, more recently, Cold War tensions between the former Soviet sphere and the Atlantic alliance.

The new pontiff also brought a view of the world that allows him to operate outside the usual diplomatic and geopolitical frameworks, reflected early on in synchronicity between Moscow and Rome on Syria. Putin credited Francis in late 2013 with helping to head off an anti-Assad Western offensive in Syria, and in general the Vatican shares Moscow’s diagnosis that trying to dislodge the Syrian leader would be a mistake.

Moreover, Putin and his Orthodox allies were edified in 2014 when Francis and his Vatican team didn’t come down harder on Russia for its incursion into Eastern Ukraine. At one stage Francis even outraged his own Greek Catholic Church in Ukraine, the largest and most influential of the Eastern churches in communion with Rome, by describing the conflict in the country as “fratricidal” – suggesting it’s largely internal, rather than the result of Russian aggression.

That thaw between Moscow and Rome culminated in a first-ever summit between Francis and Patriarch Kirill of Moscow in Havana, Cuba, in February 2016, while the pontiff was on his way to Mexico. The joint declaration the two men released afterwards further inflamed Greek Catholic sentiment by referring to them as “uniates,” a disparaging term long since abandoned in most official ecumenical discourse.

The joint declaration also pointedly avoided any criticism of Russian policy in Ukraine, or any mention of the suffering of Ukrainian Catholics during the Soviet era.

All of this has brought backlash against the pope. Critics charge him and the Vatican with excessive “ecumenical correctness,” insisting that he should be more outspoken on Ukraine, and that he should challenge the Russian Orthodox to drop their hostility to the Greek Catholics and the Eastern churches generally.

Basically, those Catholics think the Russians always want ecumenical dialogue to be on their terms, and they’d like to see the pope remind them who the real 800-pound gorilla of Christianity is.

One might suspect that the Vatican’s kid-gloves treatment is related to protecting the interests of Catholics inside Russia itself, but that’s not generally their impression.

“Since our own Church is small and weak by itself, we should be pleased if these contacts with the Holy See have helped achieve a few small steps, if nothing more,” said Monsignor Igor Kovalevsky, secretary-general of Russia’s Catholic bishops’ conference, in an interview in May with the National Catholic Reporter.

“But they all seem to be happening over our heads without much reference to local conditions,” Kovalevsky said, suggesting that whatever the Vatican is after in its détente with Moscow, fostering the growth and strength of the local Church doesn’t appear to be high on the to-do list.

All this may be coming to a head soon if, as expected, the Ecumenical Patriarchate of Constantinople, the traditional “first among equals” in the Orthodox world, recognizes the “autocephaly,” or independence, of the branch of the Orthodox church in Ukraine that’s not currently part of the Russian Orthodox Church.

Leaders of the independent Ukrainian church had hoped the decree, formally known as a tomos, would be issued before July 28, when the 1,030th anniversary of the Baptism of Kievan Rus’ will be celebrated. It now appears the earliest it may come is August, when the synod of the Ecumenical Patriarchate next meets.

Ukrainian Orthodox are expressing confidence in the eventual outcome, especially after the bid for autocephaly was backed by the country’s President, Petro Poroshenko, and the national parliament in April.

Though the Greek Catholic Church officially takes no position on internal Orthodox matters, it’s an open secret that most Ukrainian Catholics back the autocephaly drive, seeing it as an important step towards a truly independent Ukraine not forever taking its cues from Moscow. On a practical level, members of the Greek Catholic and Ukrainian Orthodox churches collaborate deeply on a wide variety of fronts and have long-standing theological dialogues.

The Russian Orthodox, however, have warned of a “schism” on the order of 1056 should Constantinople pull the trigger, and the scene appears set for a major showdown in the Orthodox world.

Back in May, in an audience with visiting Russian clergy led by Metropolitan Hilarion of Moscow, Francis made some comments interpreted in official Russian outlets as friendly to their position.

“The Catholic Church, the Catholic Churches should not interfere in the internal affairs of the Russian Orthodox Church, not even in political matters,” Francis said in that session. “This is my position and the position of the Holy See today. Those who meddle do not obey the Holy See.”

The question going forward may be how far Francis and the Vatican are prepared to go to placate Russian sensitivities, assuming the decree does happen.

For instance, when the Vatican is organizing ecumenical summits in the future, will they omit the autocephalous Ukrainian Orthodox Church from the guest list, in order to secure Russian participation?

Earlier this year, there were rumors about a second summit between Francis and Kirill – possibly when the pope traveled to Bari in Italy on July 7, or later, when he travels to the Baltics in September.

Would the Vatican be prepared to distance itself from Moscow’s Ukrainian rivals – and, thus, the sentiments of most of their own flock on the ground – in order to make that happen?

Granted, there’s a great deal at stake. The Russian Orthodox represent somewhere between half and two-thirds of all Orthodox believers in the world, depending on how you count, and there’s no serious ecumenical endgame in which they’re not involved.

Moreover, Russia is a major world power, and if the Vatican wants to act as a voice of conscience on the global stage, engagement with Putin and his team is the only realistic option.

Yet as with Trump, albeit in a very different key, the question that appears destined to plague Francis going forward is how much is too much – when flexibility and pragmatism, in other words, turn into craven placation.

So far, the verdict would appear to be that for both men, the answer remains a work in progress.