Ukraine’s drone war reaches deeper into Russia as Moscow claims another Kharkiv gain

Overview

Updated 5 days ago

Since early December 2025, the war has featured intensified winter ground operations in Kharkiv and Donetsk alongside massive drone and missile campaigns targeting each side's war economies. Russia's February 16-17 barrage of 425 drones and 29 missiles coincided with Geneva talks that concluded February 18 with limited military progress but no political breakthroughs on territorial compromises or security guarantees. Zelenskyy deemed the outcomes 'not sufficient' and requested a follow-up meeting later in February.

Ukraine responded with deep strikes, including a February 21 hit on the Votkinsk missile plant 1,300 km inside Russia using indigenous cruise missiles, and reported marginal advances in central Kupyansk as of February 19. Russia's stalled momentum in Kharkiv, where Ukrainian forces are repelling assaults near Kupyansk, contrasts with Ukraine's expanding deep-strike reach into Russian defense production.

Zelenskyy has signaled readiness for ceasefire monitoring but highlighted territorial issues as the impasse, while Russia launched further drone waves (120+ on February 20). Viability questions surround U.S.-European security guarantees amid Trump's June deadline and Congressional hurdles, while Geneva diplomacy remains fragile as Russia insists on maximalist goals beyond territory. With Ukraine's fastest gains since 2023 now tempered by attritional fighting, the economic-military toll endures amid diplomatic deadlock.

Why it matters

Russia and Ukraine now trade near-record drone barrages that hit oil ports and missile plants, pulling energy and arms production into the crossfire.

Questions about this story

Free account needed to ask — your question is kept and asked for you right after sign-up. Answers are public.

No questions yet — be the first to ask.

Play on this story Voices Debate Who Said What? Predict Higher or Lower Timeline Connections

Key Indicators

15 km

Ukrainian advance north of Lyman

Drone-led 3rd Corps counteroffensive pushed Russian forces back up to 15 km, carving a 5 by 10 km salient and cutting a key supply road near Drobysheve.

800

Russian jet-powered drones in four days

Late August barrage strained Ukrainian air defenses; about half of 174 drones in the Sept 2 attack were jet-powered models that are hard to stop.

516

Drones in Ukrainian wave at Ust-Luga

Strike on Russia's biggest Baltic oil port caused a fire; Russia claimed 516 drones destroyed overnight across Russia, Crimea, and the Black Sea.

130

Sq km Ukraine liberated in August

Ukraine recaptured 130 sq km while Russia seized just over 90, as the fight for Kostiantynivka sapped Russian troop strength.

263

Russian air defense elements destroyed in 2026

Ukraine's Unmanned Systems Forces destroyed 33 in August alone, opening corridors for drones against refineries and ports.

Voices

Curated perspectives — historical figures and your fellow readers.

Ever wondered what historical figures would say about today's headlines?

Play

Exploring all sides of a story is often best achieved with Play.

Most of these play right now — no account needed. Sign up to save scores, keep a streak, and unlock Debate and Predict. Log in Sign Up

Predict 9 ways this could play out. Back the one you believe — contrarian picks score more when a scenario has a resolution date. Log in to play

People Involved

Vladimir Putin

President of Russia

Facing renewed pressure as Ukrainian forces push north of Lyman and drone strikes hit Russian oil infrastructure

Volodymyr Zelenskyy

President of Ukraine

Exchanged threats with Putin as Russia's jet-powered drone barrages hit Kyiv; Kyiv officials warn the war could persist through winter

Robert “Magyar” Brovdi

Commander, Ukraine’s Unmanned Systems Forces

Public face of Ukraine's widening long-range strike campaign; force destroyed 33 Russian air defense elements in August

Ihor Obolienskyi

Commander linked to Ukraine’s Khartiia Corps (National Guard)

Claiming operational success around Kupiansk

Mark Rutte

NATO Secretary General

Continues to press NATO allies for sustained support as drone barrages intensify

Donald Trump

President of the United States (2025-)

Setting June 2026 deadline for peace settlement; using security guarantees as negotiating leverage; conditioning signing on finalized details

Bart De Wever

Prime Minister of Belgium

Blocked EU plan to use frozen Russian assets for Ukraine loan, citing risk to Euroclear

Andriy Biletsky

Brigadier General, Commander of Ukraine's 3rd Corps

Leading drone-led counteroffensive north of Lyman

Organizations Involved

Ministry of Defence of the Russian Federation

National defense ministry

Issuer of territorial and air-defense claims shaping Russia’s momentum narrative

Russia’s defense ministry is the main engine for official claims of captures and drone shoot-down totals.

Unmanned Systems Forces of the Armed Forces of Ukraine

Military command

Destroyed 33 Russian air defense elements in August; year total 263; expanding strikes on refineries

Ukraine’s drone force is trying to turn range into leverage by hitting production and supply nodes inside Russia.

Security Service of Ukraine (SBU)

State security and intelligence agency

Conducting deep-strike operations 1,600km inside Russia; expanding chemical and energy infrastructure targeting

The SBU is repeatedly linked to Ukraine’s most ambitious deep-strike operations.

Euroclear

Financial market infrastructure (clearinghouse / CSD)

Closed-door preliminary hearing held Jan 16 in Moscow lawsuit; Russia seeks over $225 billion over frozen €193 billion assets

Euroclear sits on the pressure point where sanctions, financing, and retaliation collide.

European Union

Supranational bloc

Approved €105B loan via market borrowing; rejected frozen-asset backing after Belgian opposition

The EU is testing a new kind of war finance: using frozen sovereign assets without full confiscation.

Timeline

December 2025 September 2026

39 events Latest: 6 days ago Showing 8 of 39

Tap a bar to jump to that date

September 2026
Ukraine strikes Ust-Luga port as 516 drones swarm Russian skies
Latest Strike

Ukrainian drones hit Russia's biggest Baltic oil port, Ust-Luga, starting a fire. Russia's defense ministry claimed 516 drones destroyed overnight over 18 Russian regions, Crimea, and the Black Sea.
6 days ago
Drone-led Ukrainian counteroffensive pushes Russian forces back 15 km near Lyman
Battlefield

Ukraine's 3rd Corps carved a 5 by 10 km salient into Russian defenses north of Lyman near Drobysheve, cutting a key supply road. An ISW assessment from Aug 31 showed Ukrainian forces at Zarichne's outskirts, threatening a 15 by 45 km encirclement pocket.
6 days ago
Ukraine liberated 130 sq km in August; Russia gained just over 90
Battlefield

ISW estimated Ukraine recaptured 130 sq km in August while Russia seized just over 90 sq km, as the fight for Kostiantynivka sapped Russian troop strength.
6 days ago
Russia fires 174 drones, half jet-powered; Putin and Zelenskyy trade threats
Strike

Russia fired 174 attack drones, about half jet-powered models that are hard to stop, plus two ballistic and two cruise missiles, per the Ukrainian Air Force. Putin and Zelenskyy exchanged threats as strikes hit both countries.
September 2nd, 2026
Ukraine fires nearly 800 drones at Russia
Strike

Ukrainian forces launched one of their biggest drone attacks of the war, firing almost 800 drones two days after a similar salvo. A Russian missile strike on a Kharkiv village killed at least 10 people the same day.
September 1st, 2026
August 2026
Russia fires 800 jet-powered drones into Ukraine in four days
Strike

Russia launched about 800 jet-powered drones over four days, mixing daytime waves that kept Kyiv under air alert for hours. Eight alerts sounded by lunchtime Monday.
August 31st, 2026
February 2026
Russia launches 120 drones and Iskander-M at Ukraine
Strike

Overnight attack from multiple regions; Ukraine downed 106 drones, debris and hits in 11+ locations including Odesa (2 injured).
February 20th, 2026
Ukrainian forces advance marginally in central Kupyansk
Battlefield

Geolocated footage confirms slight gains amid Russian assaults near Petropavlivka, Fyholivka; no major Russian advances.
February 19th, 2026
Geneva trilateral talks end without political agreement
Diplomacy

Talks conclude abruptly after 2 hours; military ceasefire monitoring discussed constructively but political issues (territory, guarantees) stalled; Zelenskyy calls results insufficient.
February 18th, 2026
SBU strikes Metafrax Chemicals plant 1,600km inside Russia
Strike

Ukraine's Security Service Alpha unit conducted deep-strike drone operation hitting Metafrax Chemicals in Perm Krai, one of Russia's largest methanol producers. At least 6 explosions reported; facility produces hexamine, urea, and pentaerythritol—key explosives components.
February 17th, 2026
Ukraine strikes Taman oil terminal in Krasnodar for second time since January
Strike

SBU drones hit Russia's largest Black Sea oil facility; second attack on terminal since January 22.
February 17th, 2026
Geneva trilateral talks begin with military chiefs; Russia launches 425 drones and missiles
Diplomacy/Strike

US-brokered negotiations between Ukraine, Russia, and US resumed in Geneva with military delegations present. Coinciding with talks, Russia launched 396 drones and 29 missiles targeting energy infrastructure; Ukraine intercepted 367 drones and 25 missiles. Over 28,000 consumers lost power in Kharkiv; tens of thousands without heating in Odesa.
February 16th, 2026
Ukraine reports fastest territorial gains since 2023—200 km² in five days
Battlefield

Ukrainian forces retook 200 square kilometers of previously Russian-occupied territory during Feb 10-15 operations, marking fastest gains in nearly three years.
February 16th, 2026
Zelenskyy addresses Munich Security Conference; demands 20-50 year US guarantees
Diplomacy

Ukrainian president told world leaders that security guarantees are key to ending war; emphasized need for Congressional backing and longer-term commitments to restore investor confidence.
February 13th, 2026
Trump using security guarantees as leverage in peace negotiations
Diplomacy

US official revealed Trump conditioning security guarantee signing on finalizing all details first; Trump wants agreement finalized before signing to avoid impeding further talks.
February 13th, 2026
Zelenskyy pushes back on Trump's summer deadline for peace deal
Diplomacy

Ukrainian president told Munich Security Conference that Congress must vote on security guarantees; warned that Kremlin is stringing US along in talks to normalize relations and ease sanctions.
February 12th, 2026
Small non-combat-capable Russian group remains trapped in Kupiansk
Battlefield

Ukrainian defense forces report only a small, non-combat-capable group of Russian troops remains in Kupiansk; Russian forces attempting to advance east toward Kupiansk-Vuzlovyi but failing to break through.
February 11th, 2026
US and Russia agree to resume military dialogue after Abu Dhabi talks
Diplomacy

Hotlines reestablished following US-brokered peace discussions; Ukraine secures prisoner exchange of 150 servicemen amid Zelenskyy's call for security guarantees.
February 5th, 2026
Ukraine strikes Oreshnik missile production infrastructure in Russia
Strike

Defense Forces confirm long-range hits on facilities linked to Oreshnik IRBM amid ongoing drone campaign.
February 5th, 2026
Russia launches record 521-drone/missile barrage before Abu Dhabi talks
Strike

Largest single attack of war with 450+ drones and 70+ missiles targets energy infrastructure; Zelenskyy urges more air defenses amid blackouts.
February 2nd, 2026
January 2026
Moscow court holds closed preliminary hearing in Russia vs Euroclear lawsuit
Legal

Russia seeks $232B over frozen assets; judge seals proceedings at Central Bank request amid EU loan debates.
January 16th, 2026
Russia rejects European peacekeeping plan as 'axis of war'
Statement

Moscow called UK-France peacekeeping proposal dangerous; vowed to treat any such units as legitimate military targets.
January 8th, 2026
Russia deploys Oreshnik missile against Lviv region
Strike

First Oreshnik intermediate-range ballistic missile use in over a year; SBU confirmed fragments recovered from Lviv strike.
January 8th, 2026
Massive 242-drone Russian strike hits Kyiv in freezing weather
Strike

Russia launched 242 drones and 36 missiles at Ukraine; Kyiv bore brunt with 4 dead, 19 injured, water and power disruptions during extreme cold.
January 8th, 2026
Zelenskyy says US security guarantee text ready for Trump finalization
Diplomacy

Ukrainian president announced bilateral security guarantee document is essentially ready for highest-level finalization with incoming Trump administration.
January 8th, 2026
Western allies agree Ukraine security guarantees framework
Diplomacy

U.S.-led monitoring mechanism and European multinational peacekeeping force agreed after Paris talks; UK-France to establish military hubs in Ukraine post-ceasefire.
January 6th, 2026
Russia launches 205+ drones at Ukraine; million lose power
Strike

New Year attack targeted energy infrastructure in seven regions; Zaporizhzhia and Dnipropetrovsk hit hardest, cutting power to ~1M people.
January 1st, 2026
December 2025
Ukrainian drones strike Russian energy sites on New Year's Eve
Air War

Drones hit energy infrastructure and homes across Krasnodar region; oil refinery and dock struck in Tuapse, 2 injured.
December 31st, 2025
Putin claims Russia seized 5,100+ sq km of Ukraine in 2025
Statement

Year-end messaging emphasized momentum; Putin claimed half of Lyman and all of Vovchansk in Kharkiv region, though ISW estimated max 7% Lyman control.
December 25th, 2025
EU approves €105B Ukraine loan without using frozen Russian assets
Money Moves

EU leaders chose market borrowing over controversial loan backed by Russian reserves after Belgian PM rejected plan as legally risky to Euroclear.
December 19th, 2025
Ukraine claims destruction of Kupiansk infiltration pipeline
Strike

Ukraine's 429th Drone Regiment released video showing destruction of a pipeline Russia used to move troops into Kupiansk.
December 13th, 2025
Zelensky visits Kupiansk as Ukraine claims an encirclement
Battlefield

Ukraine said it retook northern districts and cut supply lines, trapping Russian troops in the city center.
December 12th, 2025
Russia’s central bank sues Euroclear as EU weighs asset-backed Ukraine financing
Money Moves

Moscow called any use of its frozen assets illegal and opened a legal front against Euroclear.
December 12th, 2025
NATO messaging hardens as drone war widens
Statement

NATO’s secretary general warned the threat could extend beyond Ukraine, pressing allies toward urgency.
December 12th, 2025
Russia reports 287 drones shot down; Moscow airports disrupted
Air War

Russia said air defenses downed drones across many regions, including near Moscow, amid flight restrictions.
December 11th, 2025
Ukraine confirms strikes on Russian chemical plants tied to explosives
Strike

Ukraine’s unmanned forces said drones hit plants in Novgorod and Smolensk regions producing key inputs.
December 11th, 2025
Russia claims it captured “Lyman” in Kharkiv region
Battlefield

Russian state-linked reporting cited the defense ministry saying Lyman fell; independent confirmation was limited.
December 11th, 2025
Mass strike night: drones and missiles slam Ukrainian infrastructure
Strike

Ukraine reported a huge overnight attack wave hitting infrastructure, with energy a main target.
December 8th, 2025
Russia signals a winter push with bold capture claims
Battlefield

Russia claimed major gains in the east, feeding a momentum narrative as winter began.
December 2nd, 2025

#timeline [x-show="expanded"] { display: revert !important; opacity: 1 !important; } #timeline .timeline-toggle-btn { display: none; }

Historical Context

3 moments from history that rhyme with this story — and how they unfolded.

2022-05 to 2022-10

Battle of Lyman (2022): Capture, then sudden reversal

Russia captured Lyman during its 2022 offensive, then lost it months later after Ukraine’s counteroffensive momentum shifted the map fast. Lyman became a symbol of how “done deals” on the ground can snap back when logistics fail and pressure concentrates.

Then

Ukraine retook Lyman, puncturing Russia’s narrative of irreversible gains.

Now

Lyman stayed a recurring flashpoint tied to rail hubs and Donbas approaches.

Why this matters now

It’s the cautionary tale behind every new “capture” claim: control can be temporary.

2022-10 to 2023-03 (recurring in later winters)

Winter energy campaign against Ukraine

Russia used missiles and drones to target Ukraine’s power and heating systems, aiming to freeze civilians and strain governance. Ukraine adapted with dispersion, repairs, and air-defense layering, but each winter became a test of endurance.

Then

Blackouts and damage were severe, but Ukraine avoided systemic collapse.

Now

Energy infrastructure became a standing battlefield, not a one-off target set.

Why this matters now

Today’s drone escalation is a continuation of winter-as-weapon—now hitting both directions.

2023-01 to 2025-12

Deep-strike drone normalization (2023–2025)

What began as sporadic drone hits evolved into campaigns: refineries, depots, airfields, and now industrial inputs like chemicals and offshore platforms. Air defense became a national economic factor, not just a military one.

Then

Both sides learned to live with frequent rear-area attacks and disruption.

Now

The war expanded into a persistent contest over production, repair capacity, and investor confidence.

Why this matters now

The 287-drone wave is less an anomaly than a marker of a new baseline.