Poland scrambled fighter jets overnight as Russian strikes hit the Volyn region of western Ukraine, directly on the Polish border, cutting electricity to 370,000 people. No airspace violation was recorded, but the pattern is now unmistakable: Russia is systematically probing the defensive perimeters of NATO's eastern flank, and the probing is escalating from airspace intrusions to kinetic strikes on commercial shipping. The immediate trigger for Bulgaria's formal NATO request was a drone strike on a commercial vessel that sank off its coast on Tuesday. At least seven cargo ships have been hit in Romanian and Bulgarian territorial waters in recent weeks, killing two people with 25 still missing. Bulgarian Prime Minister Rumen Radev acknowledged that evidence points to Russia but said his government lacks definitive proof — a diplomatic hedge that did not prevent Defence Minister Dimitar Stoyanov from requesting NATO combat aircraft and anti-drone systems the same day. The geography tells the story. Russia struck western Ukraine's Volyn region hard enough to black out 370,000 people on the Polish border. In the east, drone attacks killed three in Kharkiv and injured five. In central Ukraine, an apartment block in Uman was hit. Private power company DTEK imposed emergency cuts across Kyiv. The campaign is designed to demonstrate reach across Ukraine's entire depth while testing how close to NATO territory Russia can operate without triggering an Article 5 response. Ukraine continued its own escalation. Russia reported shooting down 644 Ukrainian drones overnight, with 94 targeted at Moscow. Four Moscow airports and St. Petersburg's Pulkovo suspended operations. Ukraine's attacks on Russian energy infrastructure — particularly oil refineries — remain strategically effective but politically costly: Donald Trump has blamed Ukraine for pushing up global oil prices, creating a wedge between Kyiv and its most important backer. The Black Sea is now the sharpest edge of this escalation. Romania, Moldova, Poland, and the Baltic states have reported drone intrusions since summer, but the shift from airspace violations to attacks on commercial shipping in NATO member territorial waters represents a qualitative change. Bulgaria has proposed a moratorium on attacks on civilian ships and expects to join a NATO anti-drone initiative by late October. Stoyanov plans to meet Romanian and Turkish counterparts to coordinate a common Black Sea approach. The structural dynamic is clear: Russia is testing NATO's tolerance gradient — the distance between provocation and response. Each unanswered escalation moves the line. Poland scrambling jets is defensive routine. Bulgaria requesting NATO combat deployments is a step toward the kind of forward posture that makes miscalculation more likely on both sides. NATO has not responded to Bulgaria's request. That silence is the signal worth watching.