Will Putin Cross the NATO Line?
On September 16, Wikistrat hosted Russia analyst Keir Giles to assess which of NATO's lines Moscow has actually approached, what conditions would have to hold before it crossed one, and where the alliance is least prepared to notice
Webinar Recording:
Keir Giles is an Associate Fellow with the Russia and Eurasia Programme at Chatham House, specializing in Russian military strategy, information warfare, and cybersecurity. He previously worked with BBC Monitoring and the UK Defence Academy on Russian military and security affairs. He is a frequent commentator in international media and the author of American Overthrow: Moscow's Endgame in its Long War with Washington (2026).
Key Insights
1. The September cluster continues a process that started in 2023
Every time these incidents bunch together, the media asks whether this is the escalation everyone has been waiting for. They belong to one slow testing campaign that shifted focus, from European communications and transport links in 2023 and 2024 to the logistics feeding weapons into Ukraine. Berlin has attributed the August drone attempt at Leipzig/Halle Airport to Russia.
2. NATO's 1949 purpose is still being fulfilled
Deterrence of an armed attack still works, and a blatant conventional attack that triggered an Article 5 discussion would come as a considerable surprise. The Kremlin still suspects the muscle memory of the US armed forces would protect any ally that got tested, and American forces and installations remain in Europe doing their jobs.
3. Nobody has drawn a line below Article 5
Neither NATO nor individual member states have said which sub-threshold attacks are unacceptable. Sabotage, arson, and attacks on defense firms across Europe sit below the threshold the alliance was built to defend, and no one has defined the point at which they stop being tolerable. The gap has been open since these operations resumed in 2023.
4. The longer Europe waits, the more the line will cost
Russia has been pushing for the boundaries of what Europe will accept and has not found them, which may have eroded its sense of risk. The rest is a constant of dealing with Moscow across decades: the later you put up the stop sign, the more painful, expensive, and bloody it becomes to do it.
5. The EU never picked up the job NATO handed it
The 2016 Warsaw Summit split responsibilities so the EU would handle threats outside NATO's remit, and the EU has not assumed those functions. State terrorism has never really been NATO's job either, though it now appears to be trying to adapt. Its decades-long effort to define a position on cyber shows how slowly that happens.
6. Russia needs a visible gain, and that condition gets skipped
Giles sets three conditions for a crossing: Russia discerns where the line is, Russia is confident that crossing carries no serious consequences, and there is an evident benefit to crossing. Analysts dwell on the first two. Russia's standing incentive is to destroy NATO, or at minimum to prove it cannot do its job.
7. The likelier target sits behind the front line
Frontline states get named as the next candidate every time, and they have made themselves hard to coerce. The countries further back assume distance protects them and have not prepared to resist coercion. The opportunity Moscow acts on may be fleeting and short-notice, which is what NATO is worst placed to anticipate.
8. The war on Iran is good news for Moscow without being the opening
The Kremlin is watching Washington's campaign with satisfaction, given the expenditure and the toll on munitions, major assets, and people. The US military stays powerful enough to be a major problem for Moscow if challenged, so Russia takes comfort from the distraction while lacking the confidence it would need to test an ally.
9. Mobilization would let Russia build its NATO-facing force before any ceasefire
The evidence base for the mobilization consensus is thin, and the expectation has become a self-sustaining narrative while Russia draws tens of thousands of foreign citizens onto the front lines instead. If it happened, Moscow could fill the units and facilities already built along NATO's border while major combat in Ukraine continues.
10. Russia's air, naval, and cyber options came through Ukraine intact
The evisceration of Russian ground units early in the invasion created a misleading impression about everything else. The air force, the navy outside the Black Sea, cyber forces, and proxy sabotage remain available. When Russian drones spilled into Poland, Europe's frontrunner on military modernization could not handle a tiny fraction of what Ukraine absorbs nightly.
11. A post-Putin leadership already has a win it could bank
A successor could pose a greater and less restrained challenge to NATO, and would not need to escalate to claim a win. A freeze Russia could present as victory is on offer now through the US-brokered negotiations. Moscow has declined it because the Kremlin still calculates that fighting on pays better than pocketing the gains.
12. Russia believes it is already at war with NATO, and much of Europe has not turned up
Russian media has told conscription-age Russians for the whole of their political lives that the conflict is underway. The gap between that belief and the European position is the bigger problem. Some governments still avoid the issue because confronting it is inconvenient and expensive.
13. Russian confidence that Washington will stay out is the danger point
Asked for a scenario spectrum, Giles gave three:
Worst case: the same one it has always been, global thermonuclear annihilation. What makes it reachable is Moscow concluding it can act against NATO without the United States responding. Watch for what Russia might deduce from the outside world about when that moment is approaching.
Best case: a change of leadership in Moscow that stops the war overnight, which Giles calls the extreme case and probably not a plausible one. More realistically, enough support for Ukraine's own strike capabilities that Russia's capacity to do damage erodes and the pressure on Europe drops with it.
Black swan: Ukraine. The surprises have come from Kyiv, so far at the tactical and operational level. A strategic one would change the nature of the conflict and ease the challenge facing NATO.
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