Ukraine’s Deep Strikes Challenge Russian Strategic Depth
Tom Hayward | 24 June 2025
Summary
Ukraine’s ‘Operation Spiders’ Web’ destroyed or damaged 41 Russian long-range bombers in coordinated drone strikes, according to Ukraine’s SBU Security Service.
Recurrent strikes in Russia’s strategic rear are forcing Moscow to redeploy air-defence and security assets, straining its logistics and exposing gaps in its territorial defence.
Ukraine’s asymmetric warfare is challenging Russia’s traditional reliance on strategic depth.
On 1 June 2025, Ukraine’s Security Service (SBU) launched ‘Operation Spider’s Web’, deploying 117 attack drones from converted lorries positioned near major Russian air bases in Ivanovo, Olenya, Dyagilevo and Belaya. The operation, planned over a year in advance, bypassed air defence systems which have previously intercepted most drones launched from Ukrainian territory.
Ukraine’s strikes are the latest in Kyiv’s asymmetric campaign of deep strikes on Russian territory. Additional strikes targeted railway bridges in Bryansk and Kursk oblasts, in an attempt to disrupt vital supply lines to Russian forces. In May, explosions hit a base of the 47th Separate Air Assault Battalion of the 155th Guards Marine Brigade in Vladivostok, almost 7,000 kilometres from Ukraine’s border. Meanwhile, Ukraine has repeatedly targeted the Kerch Bridge linking Crimea with the Russian mainland. Its most recent attack
These strikes represent a fundamental challenge to Russia’s strategic doctrine, which has long relied on an ability to retreat into its territorial depth when under attack. This principle proved decisive against Nazi Germany in the Second World War and during Napoleon’s invasion in 1812. Its doctrine rested on the assumption that enemy forces would over-extend their supply lines and exhaust themselves advancing across vast distances. Ukraine’s attacks have turned a historic strength into a vulnerability by capitalising on Russia’s inability to protect every site from attack. Russia now faces an adversary capable of striking deep into its territory without having to sustain vast supply lines. Moscow faces a strategic dilemma: attempting to defend all of its strategic assets means defending none effectively.
The immediate battlefield impact of Ukraine’s strikes remains limited. Russia’s strategic bomber fleet is not crucial to its ongoing offensive operations, which capitalise on Russia’s numerical superiority and are continuing to advance consistently. However, the strikes significantly damage Russia’s strategic posture vis-à-vis NATO. Russia possessed approximately 55 operational Tu-95 bombers before the 1 June attacks, aircraft which are no longer in production and were intended to remain in service until 2040. With next-generation PAK DA stealth bombers years from operational deployment and TU-160M supersonic bombers produced at slow rates (2 assembled since 2022), Russia has no immediate ability to replace lost strategic assets. Strategic bombers also constitute one part of Russia’s nuclear triad. A degraded fleet constrains Moscow’s nuclear escalation options and reduces its strategic flexibility in a potential NATO confrontation. Ukraine’s strike on the Olenya airbase is particularly notable against the backdrop of heightened Russian military activity near Finland's border. Olenya’s proximity to Finland gives it immense strategic value in a confrontation with NATO, yet Ukraine’s ability to target the base constrains Russia’s ability to use its northern flank as a sanctuary for power projection towards Scandinavia.
Toshonenov/Wikimedia Commons, CC BY-SA 4.0
Forecast
Short-term (Now - 3 months)
Ukraine will almost certainly continue targeting high-value assets in Russia’s strategic rear.
Russia’s ability to prevent these attacks will very likely remain constrained by the prioritisation of air defence systems for frontline operations and the protection of Moscow airspace.
Medium-term (3-12 months)
Ukraine's innovative asymmetric tactics will likely force Moscow to increase defensive measures in the rear and pull assets away from the front lines to prevent further attacks.
Russia’s strategic bomber capability will very likely remain impaired given the cessation of production for existing models such as the Tu-95.
Russia will likely seek to accelerate PAK DA stealth bomber development, although operational deployment remains years away.
Long-term (>1 year)
Russia’s traditional reliance on strategic depth will very likely face sustained challenges as Kyiv’s deep strike capabilities continue to strengthen.
Russia will likely invest heavily in underground or hardened facilities for strategic bomber operations.
