Russian President Vladimir Putin’s re-election on Sunday to a fourth six-year term comes amid a feeling both in the West and in Moscow that he is ascendant as a global leader and that Russia has reemerged as a global superpower. However, if one scratches beneath the surface of these assertions, it’s clear that Putin faces a growing number of complex challenges that are likely to deepen in the coming months and gradually erode his political momentum. Here are a few that will be the most difficult for him to overcome.

In Syria, Russia is increasingly stuck on both the military and diplomatic fronts. On the battlefield, Putin has repeatedly boasted that Russia’s military goals in Syria have been accomplished — the defeat of extremist groups threatening the regime of Bashar Assad — and that he soon plans to draw down Russian military forces. However, given the chaotic situation on the ground — the Assad regime still controls only about one-third of the country — that seems unlikely anytime soon.

The cost of Moscow’s presence in Syria, meanwhile, continues to grow. In the past few weeks, the Russians have suffered the crash of a military transport with several senior officers on board, the downing of a Russian fighter jet by anti-government forces, a clash involving American-backed forces and Russian mercenaries that produced dozens of Russian casualties, and an attack by insurgents using drones on two of its bases. The latter reportedly damaged several Russian aircraft, and is likely to be repeated in the coming months.

There are also, despite recent regime advances, still thousands of Islamic State and al-Qaida-affiliated extremists operating in Syria, as well as many thousand embittered and heavily armed opponents of the Assad regime, who will never accept his legitimacy. A question: Is it likely that Assad’s political opponents will embrace a spirit of political reconciliation in the wake of the regime’s brutal conduct in the ongoing Eastern Ghouta campaign?

On the diplomatic front, meanwhile, Putin had hoped his 2015 military intervention would pave the way for Moscow to play a lead role in negotiating a final resolution to the civil war — one that would bolster Russia’s diplomatic influence regionally and secure its defense and commercial interests in Syria in the post-conflict reconstruction phase. Instead, it’s crystal clear, and has been for some time, that Assad has no intention of negotiating his departure from office, that the opposition will never trust him, and that countries such as Turkey and Iran have their own distinct visions for Syria’s future, and their roles in it.

Finally, there is no chance that the United States and the West will provide major reconstruction aid to Syria as long as Assad is in power. This is especially problematic for Assad (and Putin) given that America’s Kurdish-backed allies now control most of the critical oil fields in Eastern Syria. Therefore, it’s a safe bet that Assad is unlikely to have sufficient money to begin rebuilding Syria’s badly damaged infrastructure in the near future, even though this is critical to ensuring his long-term political viability. So, while Russia had hoped by this point in the conflict to present a bill to Assad for services rendered, it may instead be presented with a tab for money owed. Nearly three years on from Russia’s military intervention, then, Putin is discovering that playing both fireman and arsonist in Syria is a difficult needle to thread.

If Syria is a mess, how about the situation in Eastern Ukraine? For Putin, that’s not looking good either. Despite periodic spikes in fighting over the past few months, the front lines (as well as the negotiations for a political settlement) have been largely static. So, even if Putin (at least for now) has succeeded in preventing Kiev from pursuing closer integration with the West, the cost is steep and growing steeper by the month.

Russia’s intervention in Ukraine is continuing to prompt punishing economic sanctions from the U.S. and its European allies with no relief in sight. This at a time when Russia’s economic growth is already anemic (the World Bank forecasts GDP growth of below 2 percent through 2019) and with 20 million or so Russians already living below the official poverty rate of $180 per month. Even more ominous, the loss of access to U.S. and Western technology and investment over such an extended period is going to erode Russia’s long-term economic competitiveness.

It’s also worth noting that Russia’s intervention is steadily undermining traditionally high public sentiments toward Russia in Ukraine. According to recent polling, more than 60 percent of young Ukrainians now believe that Moscow is responsible for the escalation of the conflict, while only 5 percent blame Kiev. In short, Putin is steadily turning the next generation of Ukrainians against Russia.

Meanwhile, the U.S. has finally announced plans to provide Kiev with so-called lethal defensive aid including more than 200 Javelin anti-tank missiles and 37 launch units in the coming weeks. This equipment will certainly help Ukrainian units counter the old-model tanks that Moscow has provided to the separatists in recent years. As in Syria, then, Russia is finding that intervening in the Ukraine conflict was far easier than extricating itself.

In the run-up to the election, Putin trumpeted Russia’s resurgence under his leadership, skillfully portrayed Russia as a victim even as it acted aggressively abroad, spoke publicly (and menacingly) of Russia’s newfound military prowess, and engaged in a series of brazen acts, most notably the reported nerve agent attack against two Russians residing in England. If he intends to govern in his next term according to this script, the U.S. and its allies will have little choice but to push back hard.

Some of the options that policymakers might consider include: new and creative ways to raise the military cost to Russia for its foreign interventions; sweeping policies to further curb Russia’s access to advanced technology; measures to eliminate the ability of Putin’s cronies to hide money abroad; active cyber operations against Russian entities involved in hacking; and aggressive public messaging efforts to highlight Putin’s anti-democratic actions and expose the sources of his vast personal wealth, especially to audiences inside Russia.

It seems clear that all this adds up to a daunting set of challenges Putin faces in the coming years. And it’s certain that provoking a more intense and direct confrontation with the West is not going to make his job any easier.

Michael Dempsey is the national intelligence fellow at the Council on Foreign Relations and former acting director of national intelligence.

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