The Kupiansk Trap Is Happening Again September 24, 2026 The Setup The Russian 68th Guards Motor Rifle Division is once again trying to push across the Oskil River into the swampy, forested belt north of Kupiansk. This is the same ground, and the same division, that was gutted there last fall. Current reporting indicates that the 122nd Motorized Rifle Regiment and a second regiment, both subordinate to the 68th, are crossing the river now. Everyone can see what comes next. After last year’s success, Ukrainian units pulled back and allowed the Russians to return to the same area. Waiting for them this time is a regular Army force under a new corps that has taken over the sector: the 12th Heavy Mechanized Brigade in the lead, alongside the 151st Mechanized Brigade and the 35th and 39th Marine Brigades. In this sector, Ukraine outnumbers the attackers. Militarily, the attack makes no sense. Politically, Moscow appears to believe it needs it. What Happened Last Year In October and November 2025, the 68th sent two regiments across the Oskil north of Kupiansk with the goal of breaking through to the R-07 highway, the main supply route for Ukrainian forces around the city. Ukraine formed a dedicated grouping, led by the National Guard’s 13th Khartiia Brigade, to eliminate the breakthrough. It defeated battalions and assault units from the 121st and 122nd Motorized Rifle Regiments and the 30th Engineer Regiment, along with the 27th Motorized Rifle Brigade, then drove through to the river and cut the Russians’ ground routes into the city. The numbers tell the story. More than five battalions were destroyed. With three battalions to a regiment, that is effectively two regiments that lost all combat strength. The 68th was gutted. A Stronger Ukrainian Force This Time This year the fight is not being led by the National Guard. A new corps has taken over the area, and the regular Army is in charge. Many of these troops have been rotated in and out of the line and are rested. They are better equipped, and they outnumber the attackers. The 68th, by contrast, is an exhausted division that never fully recovered from last year. It is throwing tired troops into a bad situation against a fresher, larger, better-equipped defender. The 122nd Motorized Rifle Regiment, one of the two regiments gutted last fall, is crossing the river again. On paper and on the ground, this fight can only go one way. How the Trap Works The Ukrainian plan appears to be a repeat of last year, and there is no rush to spring it: 1.Let them cross. Russian infantry gets across the Oskil, but the river, the swamp, and the forest keep their armor, mechanized support, and most of their artillery on the far bank. 2.Let the bowl fill. Ukraine allows the pocket north of Kupiansk to fill with Russian troops who are cut off from heavy support and dependent on a fragile river crossing for every round, ration, and casualty evacuation. 3.Close the door. Once enough Russians are inside, Ukrainian mechanized and Marine forces counterattack to the river, sever the crossings, and destroy what is trapped in the pocket. The longer Ukraine waits, the more Russians walk into the bag. Patience is the weapon. Why the Russians Keep Losing This Fight The Russian Army is not built for light infantry warfare. Its doctrine, training, and culture center on massed armor and artillery. When it sends infantry forward without tanks, fighting vehicles, and guns in support, it loses, and it loses big. The pattern repeats: a costly infantry push, heavy losses, and a pullback. Russia has shown it can infiltrate small groups under drone cover, including into Kupiansk itself. But infiltration is not holding ground. Small teams without armor or artillery can harass and occupy buildings; they cannot defeat a counterattack by mechanized brigades. The Stakes for Russia If the 68th loses two more regiments here, it has effectively lost the entire division, not counting replacements. Replacement troops are not the same as a trained, cohesive formation, and rebuilding a division that has been destroyed twice on the same ground takes time Russia does not have in this sector. The River Clock The smart play for Ukraine is to let as much of the 68th Division as possible get across to the west bank of the Oskil. In about a month, the river will be flooded and cold, and crossing it, in either direction, will become nearly impossible. At that point, everything the 68th has on the west bank is cut off from reinforcement, resupply, and retreat. If Ukraine times the counterattack to the river, the division will not be mauled this time. It will be destroyed. Analysts Versus Bloggers Any serious military analyst looking at the force ratios, the terrain, and last year’s result will reach the same conclusion. Russian military bloggers will not. Expect them to announce within days that Russian troops are in the center of Kupiansk and all is well, then quietly reassess months later when the losses become impossible to hide. That cycle has played out before on this exact ground. What Could Go Wrong for Ukraine The trap is not free. Ukrainian spokesman Viktor Trehubov has described a kill zone of roughly 20 kilometers on both sides of the line, where every supply run and casualty evacuation must be planned as its own operation. Russian drones will contest every Ukrainian move to close the pocket, and waiting too long risks letting the Russians dig in. The timing of the counterattack is the whole game. Bottom Line This is a repeat of a failure everyone saw last year. Russia is feeding two regiments of the same exhausted division into the same swamp, against a larger, rested, better-equipped Ukrainian regular Army force that has already shown it knows how to close the door. With winter flooding weeks away, the Oskil will do half of Ukraine’s work. Barring a change in Russian tactics, expect the end of the 68th Division as a fighting formation, and another political attack paid for in lives.