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Operation Spiderweb: Ukraine's $7 billion drone strike

Operation Spiderweb: Ukraine's $7 billion drone strike

Force in Play
By Newzino Staff | |

How $2,000 drones destroyed a third of Russia's strategic bomber fleet

January 10th, 2026: Ukraine Strikes Zhutovskaya Oil Depot

Overview

At dawn on June 1, 2025, Ukraine's Security Service pulled off the largest covert drone strike in history. One hundred seventeen drones, smuggled into Russia inside fake shipping containers and hidden in truck cabs, launched from five locations spanning five time zones. They hit five Russian air bases simultaneously, destroying or damaging 41 strategic bombers—including irreplaceable Soviet-era Tu-95s and Tu-22M3s—worth $7 billion. The unwitting truck drivers thought they were hauling prefab houses. One died in the explosions. Four were arrested by the FSB.

The operation gutted 34% of Russia's strategic cruise missile carriers—aircraft that can't be replaced because production ended when the Soviet Union fell. Seven months later, Ukraine continues the asymmetric warfare playbook Spiderweb pioneered: in early January 2026, SBU drones struck ammunition depots and oil facilities deep inside Russia almost daily. The architect of Spiderweb, Vasyl Maliuk, resigned as SBU chief in January but stayed on to run covert operations. Meanwhile, Trump administration peace negotiations advanced with a 20-point framework, but Russia rejected European peacekeepers and showed little willingness to compromise. Spiderweb proved strategic depth is dead—and Ukraine keeps proving it.

Key Indicators

117
Drones Deployed
Launched simultaneously across five Russian time zones
41
Aircraft Hit
Tu-95, Tu-22M3, and A-50 strategic assets destroyed or damaged
$7B
Estimated Damage
vs. $300K cost to Ukraine for drones and equipment
34%
Russian Strategic Bombers Disabled
Irreplaceable Soviet-era aircraft, no longer in production
4,300 km
Deepest Strike Range
Belaya Air Base in Eastern Siberia hit from Ukrainian control

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People Involved

Volodymyr Zelenskyy
Volodymyr Zelenskyy
President of Ukraine (In office since 2019, leading Ukraine through war)
Vasyl Maliuk
Vasyl Maliuk
Head of Security Service of Ukraine (SBU) (Resigned January 2026, remains to lead asymmetric ops)
Vladimir Putin
Vladimir Putin
President of Russia (In power since 1999, leading invasion of Ukraine)
Donald Trump
Donald Trump
President of the United States (Second term, inaugurated January 2025)

Organizations Involved

Security Service of Ukraine (SBU)
Security Service of Ukraine (SBU)
Intelligence Agency
Status: Leading Ukraine's deep-strike operations

Ukraine's primary domestic intelligence and counterintelligence service, transformed into an offensive asymmetric warfare unit.

Russian Aerospace Forces
Russian Aerospace Forces
Military Branch
Status: Lost 20% of strategic bomber fleet in one day

Russia's unified air and space force, operating Soviet-era strategic bombers that can no longer be replaced.

Timeline

  1. Ukraine Strikes Zhutovskaya Oil Depot

    Military

    SBU drones hit oil depot supplying Russian forces, continuing pattern of deep strikes on logistics infrastructure.

  2. Trump Advisers Meet Russian Envoy in Paris

    Diplomacy

    Steve Witkoff and Jared Kushner discuss U.S. peace plan with Kirill Dmitriev. Russia shows little willingness to compromise.

  3. Paris Summit on Ukraine Security Guarantees

    Diplomacy

    Coalition of the Willing agrees on security guarantees framework. U.S. backs truce monitoring; UK and France pledge troops. Russia rejects European peacekeepers.

  4. SBU Strikes Ammunition Depot and Oil Facility

    Military

    Overnight drone strikes damage 100th Arsenal ammunition depot and oil facility in central Russia, disrupting military supply chains.

  5. Maliuk Resigns as SBU Chief

    Political

    Spiderweb architect steps down but stays to run covert ops.

  6. Ukraine Strikes Rosrezerv Oil Depot on New Year's

    Military

    SBU drones hit oil depot in Yaroslavl region, designed to cut Russian petroleum supply chains.

  7. Zelenskyy-Trump Meeting Advances Peace Framework

    Diplomacy

    Zelenskyy unveils 20-point peace plan after meeting Trump, claiming 90% agreement on deal terms.

  8. Trump-Putin Alaska Summit

    Diplomacy

    Three-hour meeting yields no ceasefire. Trump backs Putin's territorial demands.

  9. Russia Controls All of Luhansk

    Military

    Moscow announces full control of Luhansk oblast in Donbas.

  10. SBU Mines Crimean Bridge

    Military

    Ukrainian agents plant explosives on underwater bridge supports.

  11. Second Istanbul Peace Talks

    Diplomacy

    One-hour meeting yields prisoner swap agreement but no ceasefire progress.

  12. Operation Spiderweb Executes

    Military

    117 drones strike five Russian air bases. 41 strategic bombers destroyed or damaged.

  13. First Direct Peace Talks in Three Years

    Diplomacy

    Ukraine and Russia meet in Istanbul, first direct talks since 2022.

  14. Russia Retakes Kursk

    Military

    Moscow announces Ukrainian forces expelled from Kursk region.

  15. Trump Inaugurated

    Political

    Trump returns to office, raising doubts about continued U.S. military aid.

  16. SBU Begins Planning Spiderweb

    Planning

    Zelenskyy approves covert operation to strike deep inside Russia.

  17. Russia Invades Ukraine

    Invasion

    Putin launches full-scale invasion from Belarus, Crimea, and Donbas fronts.

  18. Russia Seizes Crimea

    Invasion

    Disguised Russian troops occupy Crimea. Conflict spreads to Donbas in April.

Scenarios

1

Ukraine Escalates Deep Strikes, Russia Retaliates Against Kyiv

Discussed by: CSIS, Chatham House, military analysts

Ukraine replicates Spiderweb against other high-value targets—refineries, ammunition depots, command centers. Russia responds with intensified missile and drone attacks on Ukrainian cities, targeting critical infrastructure. Neither side gains decisive advantage. Attrition grinds on. Trump threatens to cut aid if Ukraine doesn't negotiate. Zelenskyy faces domestic pressure to accept territorial losses. Peace talks resume under U.S. pressure with Ukraine ceding Crimea and parts of Donbas.

2

Russia Adapts, Spiderweb-Style Ops Become Ineffective

Discussed by: Defense analysts, Russian military bloggers

Moscow tightens logistics security, screens civilian trucking, deploys counter-drone systems around strategic sites. The SBU's infiltration playbook stops working. Ukraine shifts back to conventional long-range drones and missiles but faces tighter Western restrictions on deep strikes. Russia continues grinding advances in Donbas. Ukraine's asymmetric edge dulls. By late 2026, territorial losses mount and Ukraine negotiates from weakness.

3

NATO Adopts Spiderweb Tactics, Russia Faces Multi-Front Pressure

Discussed by: NATO military planners, Irregular Warfare Journal

Western militaries study Spiderweb as blueprint for low-cost strategic strikes. NATO increases support for Ukrainian covert ops. Baltic states, Poland, and Moldova quietly enable cross-border infiltration operations. Russia faces drone threats from multiple vectors. Putin escalates rhetoric about NATO aggression but lacks effective countermeasures. Pressure grows for Russia to negotiate seriously. Peace talks yield ceasefire with territorial compromises but Ukraine retains more leverage.

Historical Context

Operation Black Buck (British Falklands Raids, 1982)

May-June 1982

What Happened

RAF Vulcan bombers flew 6,600 nautical miles from Ascension Island to bomb Argentine positions in the Falklands—the longest-range strikes in history at the time. Eleven tanker aircraft refueled a single Vulcan in an elaborate relay. The raids cratered Stanley Airfield's runway, preventing Argentine jets from using it.

Outcome

Short Term

Runway damaged, Argentine fast jets unable to land.

Long Term

Demonstrated extreme-range strike capability but strategic impact debated; some analysts call it more symbolic than decisive.

Why It's Relevant Today

Both operations prioritized strategic messaging over tactical destruction—showing adversaries nowhere is safe.

Operation Entebbe (Israeli Hostage Rescue, 1976)

July 3-4, 1976

What Happened

After terrorists hijacked an Air France flight to Uganda, Israeli commandos flew 2,300 miles, raided Entebbe Airport, and rescued 102 hostages in 90 minutes. The raid required covert planning, flawless coordination across time zones, and operational surprise deep in hostile territory.

Outcome

Short Term

102 hostages freed; one Israeli commando killed.

Long Term

Entebbe became template for long-range covert operations and bolstered Israel's global reputation for bold military action.

Why It's Relevant Today

Like Spiderweb, Entebbe proved that patient planning and infiltration can achieve strategic surprise thousands of miles from home.

Pearl Harbor (Japanese Carrier Strike, 1941)

December 7, 1941

What Happened

Japanese carrier aircraft struck the U.S. Pacific Fleet at Pearl Harbor without warning, sinking battleships and destroying aircraft. The attack demonstrated the vulnerability of concentrated strategic assets to surprise strikes. It brought the U.S. into WWII and shifted naval doctrine toward carriers.

Outcome

Short Term

Crippling damage to U.S. battleship fleet; 2,400 Americans killed.

Long Term

U.S. entered WWII; Japan ultimately defeated. Strategic surprise changed warfare but didn't guarantee victory.

Why It's Relevant Today

Russian military bloggers called Spiderweb 'Russia's Pearl Harbor'—a surprise strike exposing the myth that distance equals safety.

19 Sources:
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Wikipedia CNN Chatham House CSIS PBS NewsHour Kyiv Independent The Moscow Times NPR Axios Al Jazeera The Washington Post UNITED24 Media Meduza Wikipedia Wikipedia Wikipedia Wikipedia Kyiv Independent NPR