Weekend Update #189: Can Ukraine Isolate Crimea?

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Weekend Update #189: Can Ukraine Isolate Crimea?<br>Ukraine Understands What Is Needed In Infantry; A Flamingo In Action

Phillips P. OBrien<br>Jun 14, 2026

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Hi All,<br>Before we get into the update itself this weekend, which will start with arguably the most important and fascinating part of Ukraine’s mid-range strike campaign, I just wanted to bring to your attention this Substack Live from last week. I was joined by Vladyslav Urubkov, a military analyst at Come Back Alive, who walked me through many of the technical details and strategic concepts underlining the Ukrainian mid-range campaign. It has received extraordinarily good feedback.

Live with Phillips P. OBrien and Vladyslav Urubkov<br>Phillips P. OBrien and Vladyslav<br>Jun 10

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And if you would like to support Come Back Alive and the amazing work Vladyslav and his co-workers there do, here is a donation link.<br>Phillips’s Newsletter is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

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One thing that makes this episode so topical is that, as we discussed and as we have seen over the last few days, the mid-range campaign is taking a fascinating turn. This week the Ukrainian attempt to isolate Crimea, as part of that mid-range campaign, stepped up a notch. The Ukrainians are moving to cut off as many of the transport links in and out of Crimea as possible. If they can dictate traffic flows there, Russian control will be crippled.<br>Beyond this there were a number of important stories this week. The most important of these is arguably the Ukrainian announcement of how they intend to recruit and pay their soldiers. It shows just how they are understanding their own war and moving more and more away from the terrible mass-infantry idea that was being pushed on them by western governments and the western analytical community. Limited number of the best soldiers matters more than mass of conscripts.<br>Finally, we were able to see the best pictures so far of a Ukrainian FP-5 (Flamingo) missile in action, just before it hit a Russian target. The system seems to be improving, but also—where the heck was Russian air defense?

Can Ukraine Isolate Crimea?

For those of you who do not know Crimea, it is a peninsula that juts out into the Black Sea. The only land routes into the peninsula run from from occupied Ukraine. Indeed in terms of transport there really are only two ways in—over the Kerch rail and road bridge from Russia (from the east) or down from Ukraine over either the Chonhar Bridges or the Henichesk/Syvash Bridges that go near Armiansk (from the north). I used AI to make this map—I hope it makes sense.

Up until this point in the war the Ukrainians had actually worked hard to isolate Crimea from the air and the sea. They had forced the Russians to abandon the Sevastopol naval base, meaning getting shipping in and out of the peninsula except in the far east, is very difficult. The Ukrainians have also waged a continuous campaign against Russian air defense, which means that the Russians flying supplies in and out of Crimea would be far too risky.<br>So all that is left is the road and rail bridges.<br>Until this last week. Since June 6, Ukraine has launched a comprehensive and well thought out series of mid-range UAV attacks against the road and rail network into Crimea. They were focussed on cutting off the peninsula from the north. Here is a list of the attacks from the last week—the locations can all be found on the map above.<br>June 7, 2026: The Initial Chonhar Bridge Strike<br>Target: The Chonhar Road Bridge (a primary artery carrying the R-280 highway from Rostov-on-Don into Crimea).

The Attack: Conducted overnight by Ukrainian drone units using the newly debuted “Behemoth” mid-range strike drone (equipped with a dual high-explosive and thermobaric warhead). Note—one of the advantages of the mid-range campaign for Ukraine is the shorter distances involved means that mid-range systems need less fuel and can carry heavier warheads such as this.

Impact: Satellite imagery confirmed dark impact craters on the central span, forcing Russian occupation authorities to halt traffic and deploy an adjacent pontoon bridge.

June 9, 2026: The Chonhar Follow-Up & Henichesk Closures<br>Target: The Chonhar bridge system (again) and the alternative eastern corridor.

The Attack: A second wave of long-range UAVs hit the Chonhar crossing. Simultaneously, Ukrainian forces launched an attack near the bridge linking Henichesk to the Arabat Spit.

Impact: The Chonhar road crossing was officially declared inoperable, with military bloggers noting repairs could take up to a month. The Henichesk detour was also suspended, forcing Russian military logistics to entirely shift westward toward the Perekop Isthmus (Armiansk route). It is worth looking at this map seeing how Russian logistics were getting...