Putin's Winter Strategy: ISW Warns of Escalating Drone Strikes to Force Capitulation by Spring 2027

Key points

• ISW states Putin's revised theory of victory depends on high-penetration rates of cheap Geran-type drones and ballistic missiles to break Ukrainian resistance before spring 2027.
• Russian forces are actively blocking food supplies to occupied Oleshky in Kherson Oblast, exacerbating a severe humanitarian crisis.
• A Russian drone entered Romanian airspace on the night of September 26-27, continuing a pattern of violations of European airspace.
• Ukrainian forces recently advanced in the Chasiv Yar tactical area and the Oleksandrivka direction, countering Russian ground stagnation.
• Russia launched 170 drones against Ukraine overnight on September 28, reflecting the scale of the new strike campaign.

Background

This development follows ISW's August 2026 assessment, which noted that Russian ground advances had stagnated to roughly 2.91 km2 per day, while Ukrainian counteroffensives expanded by nearly 130 km2. In August, ISW also highlighted Russia's shift toward jet-powered drones to maximize civilian harm and its inflation of ground gains through cognitive warfare. The current winter strategy represents an escalation of this drone-centric approach, aiming to compensate for lack of territorial progress through sustained infrastructure destruction.

How outlets are covering it

The ISW and UNITED24 Media emphasize that Putin's strategy relies on the assumption that Ukraine cannot sustain air defense operations through winter, particularly regarding Patriot interceptor shortages. They view the campaign as a finite attempt to force capitulation by spring 2027. In contrast, The New York Post highlights a diplomatic dimension, reporting that Putin privately told US officials he intends to escalate attacks as 'payback' for Ukrainian strikes on Russian oil refineries. The Post notes that while US officials believe Putin and Zelensky are closer to a deal than public perception suggests, Putin's demand for territorial control in Donetsk remains the primary obstacle. Kyiv Post focuses on the immediate humanitarian and military impacts, such as the blockade of Oleshky and the drone incursion into Romania, framing the situation as a broadening of the conflict's geographic and humanitarian scope.

Why it matters

The shift to a high-intensity, long-range strike campaign signals a potential escalation in the war's lethality and geographic reach, with direct implications for European security and global energy markets. The humanitarian crisis in occupied areas and the strain on Ukrainian air defenses could determine whether the conflict reaches a tipping point before the spring, influencing the viability of any ceasefire negotiations.

What to watch

Expect continued intense drone and missile strikes on Ukrainian energy and civilian infrastructure through the winter of 2026-2027. Ukraine's development of the 'Freyja' anti-ballistic missile system and its continued strikes on Russian oil refineries will likely remain central to the conflict's dynamic. Diplomatic efforts, including potential limited ceasefires on grain and energy targets, may proceed but are likely to be hindered by Putin's territorial demands and the ongoing escalation in strikes.