Russian President Vladimir Putin conducts a meeting with Russian ministers, members of parliament, lawmakers and other public cultural leaders in the Chekhov Museum on August 14, 2014 in Yalta, Crimea.
Sasha Mordovets—Getty Images
September 6, 2014 2:00 PM EDT

A few years ago, when NATO strategists would stop to consider a possible threat from Russia, their chief concern was the possibility, however slight, that the Russian state would implode, lose control of its nuclear arsenal and allow a few warheads to fall into the wrong hands. That at least was the worry Ivo Daalder expressed in the fall of 2010, when he paid a visit to Moscow as the U.S. ambassador to NATO. But on the whole, he says he just wasn’t very concerned about Russia at the time. The alliance was too busy with that year’s troop surge in Afghanistan and with newfangled threats like cyber warfare.

“As a security concern Russia wasn’t really on the agenda in 2010,” he tells TIME by phone on Friday from Chicago. “The focus with Russia was really on cooperation.”

At that year’s NATO summit in Lisbon, Russia seemed eager to play along. The military doctrine it adopted earlier that year still listed NATO expansion as the primary threat to Russian security. But Dmitri Medvedev, who was then serving as Russia’s president while Vladimir Putin took a turn as prime minister, agreed in Lisbon to cooperate with the alliance on various issues of mutual concern, such as terrorism and drug trafficking. The brief war that Russia had fought two years earlier in neighboring Georgia, an aspiring member of NATO, was duly put aside at the Lisbon summit as a bump in the road toward Russia’s cooperation with the alliance. All the while, the defense infrastructure that NATO had maintained during the Cold War to prepare for a confrontation with Russia in Europe was falling deeper into disrepair.

“NATO had for many years failed to really invest in its infrastructure in the east,” recalls Daalder, whose term as ambassador ended a year ago. “Even the basics were just very poor to non-existent.” That included things like air bases in Eastern Europe, ports, oil pipelines and other essential gear that NATO would have needed to “flush forces into the region,” he says.

Only this spring, after Russia sent troops into another one of its European neighbors – this time Ukraine – to occupy and annex the region of Crimea, NATO finally began to consider for the first time in two decades how exposed its eastern flank had become. The agenda at the NATO summit in Wales this week was shaped by this realization. But adjusting to it will take much more than the summit’s decision on Friday to station a few thousand troops in Eastern Europe on a rotating basis. It will need to adapt to a security paradigm that Russia seems to be inventing on the fly, and wiping the dust off NATO’s Cold War playbook may not do much to help the alliance find its footing on this unfamiliar terrain.

“It’s a different ball game,” says Daalder. It still involves a distinctly Soviet bag of tricks – most importantly Putin’s reminder last month of the strength of his nuclear arsenal – but Putin’s actions in Ukraine have also displayed a new type of shape-shifting warfare, one that is far more nimble and unpredictable than anything the stodgy old men of the Politburo were able to muster.

Take, for instance, the standoff unfolding along the Russian border with Estonia, one of the NATO allies that is, by virtue of geography and demography, most susceptible to Russian meddling. Not only does it share a border with Russia that is nearly 200 miles long, but its population is roughly a quarter Russian, forming an ethnic minority whose rights Putin has promised to “protect” by any legal means. These vulnerabilities were among the reasons Barack Obama chose to visit Estonia on Wednesday in a show of solidarity. During a speech in the capital, the U.S. President pledged his military would come to Estonia’s defense if it were ever attacked or invaded. “An attack on one is an attack on all,” Obama said, echoing Article 5 of NATO’s founding treaty, which obliges all members to defend any ally that faces a foreign attack.

Two days later, as the summit in Wales was winding down, Estonian President Toomas Hendrik Ilves sounded the alarm over what he reportedly called an invasion of Estonian territory. He and other senior officials from his government said that unknown assailants had come from Russia and abducted an Estonian security service officer at gunpoint, allegedly using smoke bombs and jamming the radios of Estonian border guards during the Friday morning raid.

Russia made no secret of its involvement. The security service known as the FSB (the post-Soviet incarnation of the KGB) told Russian news agencies that it had the officer in custody on suspicion of spying, but claimed he had been arrested on the Russian side of the border, not in Estonia. Given the timing, some Estonian officials saw the move as a blatant Russian provocation, not only against their country but the whole of NATO.

“This is a demonstrative show for the United States and other Western countries that [Russia] does what it wants in this part of the world,” Urmas Reinsalu, an Estonian lawmaker and former minister of defense, told the Postimees newspaper. Another prominent Estonian politician, Eerik-Niiles Kross, who formerly served as the country’s intelligence chief, told local media that the kidnapping “should be filed under ‘rewriting the rules.’”

That seems like a fair term for what Russia has been doing in Ukraine all year. With its annexation of Crimea in March, Russia redrew the borders of Europe and, as Daalder puts it, “threw out the rulebook of post-Cold War security policy.” The new rules will depend primarily on the way NATO responds. So far, Obama has made clear that his “red line” is the border of the NATO alliance, and if Russia violates that border, the U.S. would respond with force. But what exactly would constitute such a breach? A full-on tank invasion or something more subtle?

It is through such ambiguities that Russia has been testing NATO’s resolve, prodding and provoking to feel out the alliance’s weak spots. And it isn’t the first time Russia’s done this. During Estonia’s noisy 2007 spat with Russia over a Soviet war memorial, Russian hackers launched a massive cyberattack against Estonia that paralyzed the websites of its government, parliament, banks and media. Estonian officials blamed the Kremlin, and questioned whether a cyberattack of this or any other magnitude could trigger Article 5 of the NATO treaty. At the Wales summit this week the allies finally affirmed that it could, even suggesting that the NATO could launch a military response to a cyber threat. This seemed to patch a key hole in the alliance’s remit.

So what about the arrest of the Estonian security official on Friday? Would that qualify as an invasion if the government proves that Russian agents crossed into Estonia and kidnapped him at gunpoint? Probably not. Even after the U.S. and NATO claimed last month that Russia had sent thousands of troops into Ukraine, Obama stopped short of calling it an invasion.

At some point Russia’s aggression may become blatant and destructive enough to trigger NATO’s allied response. But the crucial question is where that point would be, and whether it even exists. Some observers have begun to doubt it. Last month the Russian political scientist Andrei Pointkovsky proposed a thought experiment on this question involving the potential flashpoint of Estonia.

The population of the border city of Narva, he pointed out, is predominantly Russian, and the Kremlin could in theory try to stir an ethnic rebellion in Narva much as it did among the ethnic Russians in Crimea this spring. NATO would then have to consider whether such an incursion breaches Obama’s red line, but in the meantime, Putin could in theory decide to launch a “very limited” nuclear strike against a NATO city, Pointkovsky wrote. What would the West do then?

“Put yourself in the place of Obama, the Nobel Peace Prize laureate . . . The progressive and even the reactionary American public would cry out in unison that, ‘We don’t want to die for f—ing Narva, Mr. President!,” wrote Pointkovsky.

In Pointkovsky’s assessment, it is far from clear how the U.S. would respond to this doomsday scenario, and Daalder agrees. “Do I know for certain that if the Russians would use nuclear weapons against Poland that we would retaliate? No,” says the former ambassador. The Western assumption, he says, is that Putin would not take such a gargantuan risk, that even the slight possibility of a NATO counter-strike would be enough to deter him. This logic, known among defense wonks as Mutually Assured Destruction, is what prevented the U.S. and the Soviet Union from ever starting a nuclear war.

It has been a generation since the West has really been forced to consider whether such thinking is sound. But based on the wording of its official military doctrine, which was adopted in 2010, Russia has been thinking about this all along. A senior Russian general even suggested this week that the doctrine should be revised to allow for the possibility of a “preventative” nuclear attack against the West. This issue did not come up at the NATO summit in Wales, at least not publicly, but Daalder suggests it may be time to assess Russia’s reasoning. “We haven’t thought about deterrence in a long time, and we need to do it again,” he says. The expiration date has clearly past on NATO’s infrastructure in Eastern Europe, but its mentality in standing up to Russia may also be due for an update.

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