Daniel sent us this one — he's been listening to that episode on Live UA Map and the OSINT community, and it got him thinking about the war in Ukraine itself. He calls it an unvarnished, old-school invasion without justification, and he's wondering about the major turning points, what Russia actually claimed as their reason for going in, the history of Ukraine as a territory, and where things stand now in terms of territory held and daily life during the war. Also, he connects this to something a lot of people here in Jerusalem think about — if sanctions didn't stop Russia, what does that say about diplomacy with Iran?
That's a meaty one. And he's right about the OSINT connection — a huge amount of the open source intelligence tradecraft that people now take for granted was forged in Ukraine starting in twenty fourteen, not even twenty twenty-two. The Live UA Map team being based there makes complete sense because Ukrainians have been crowdsourcing conflict data since the first Donbas incursion. But let's get into the actual war he's asking about.
Before we do — quick note, DeepSeek V four Pro is writing our script today. There, done, moving on. So Herman, let's start with what Daniel called the Russian excuse. What did Moscow actually claim was the reason for the full-scale invasion in February twenty twenty-two?
Putin laid out several justifications in that speech on February twenty-fourth, but they boil down to three things. First, he claimed NATO expansion was an existential threat — that the alliance had broken a supposed promise not to expand eastward after the Cold War. Second, he framed it as a "special military operation" to "denazify" Ukraine, which is an absurd framing given that Ukraine's president is Jewish and the country has a democratically elected government. And third, he claimed Russia was protecting Russian speakers in eastern Ukraine from genocide — allegations that have been thoroughly debunked by organizations like the OSCE and the UN Human Rights monitoring mission.
The "denazify" thing — that's the one that really lands as pure propaganda when you look at it for more than five seconds.
It's completely ahistorical. Ukraine does have far-right groups, like pretty much every European country does, but they're politically marginal. In the twenty nineteen parliamentary elections, the far-right Svoboda party got about two percent of the vote. The Azov Battalion, which Russia constantly points to, was integrated into the Ukrainian National Guard years ago and its political wing has zero parliamentary seats. Meanwhile, Russia's own Wagner Group uses neo-Nazi symbolism extensively, and the Russian Imperial Movement is a designated terrorist organization in multiple countries. The whole framing is projection.
That's the stated excuse. But let's rewind further, because Daniel asked about the history of Ukraine as a territory. A lot of people talk about this conflict like Ukraine has always been Russia's backyard, and I think that misses quite a bit.
It misses everything, really. Ukraine has a distinct history that goes back well over a thousand years. Kyivan Rus, which was centered on Kyiv, not Moscow, was a major medieval state from the ninth to the thirteenth centuries. Moscow was a minor outpost at the time. The idea that Ukraine is somehow a historical appendage of Russia is a nineteenth-century imperial narrative that Putin has revived for political purposes.
There's a whole period where large parts of western Ukraine weren't under Russian control at all.
After the Mongol invasion fragmented Kyivan Rus, western Ukraine fell under the Polish-Lithuanian Commonwealth, then the Habsburg Empire. For centuries, Lviv and the surrounding regions had more connection to Vienna and Warsaw than to Moscow. The eastern parts and Crimea were gradually absorbed into the Russian Empire from the seventeenth century onward, but even then, Ukrainian identity and language persisted despite repeated attempts at Russification. The Soviet period added another layer of tragedy — the Holodomor in nineteen thirty-two and thirty-three, a man-made famine that killed millions of Ukrainians, was essentially Stalin's effort to break Ukrainian resistance to collectivization. That's not ancient history — people's grandparents remember it.
When Putin says Ukraine isn't a real country, he's not just making a political argument — he's erasing a thousand years of distinct identity.
That erasure is the ideological core of the invasion. In July twenty twenty-one, Putin published an essay called "On the Historical Unity of Russians and Ukrainians" that laid this all out. He argued that Russians and Ukrainians are one people and that Ukrainian sovereignty is an artificial construct. If you read that essay, the invasion makes more sense — not as a rational act, but as an ideological project. He genuinely seems to believe it.
Which brings us to the invasion itself. February twenty twenty-two. What were the actual turning points Daniel's asking about?
I'd break it into phases. The first phase, February to April twenty twenty-two, was Russia's attempt at a decapitation strike. They pushed toward Kyiv from Belarus in the north, toward Kharkiv in the northeast, and from Crimea in the south. The expectation — and this is well-documented in captured Russian military plans — was that Kyiv would fall within days, the government would flee, and a puppet regime would be installed.
That obviously didn't happen.
It failed for several reasons. One, Ukrainian resistance was far more determined than Russian planners anticipated. Two, Russian logistics were catastrophically bad — there's that famous forty-mile armored convoy north of Kyiv that sat stalled for weeks because of fuel shortages, mud, and constant Ukrainian ambushes. Three, the Russian military's command and control was a mess. They were using unencrypted radios, getting picked off by Ukrainian special forces. By early April, Russia withdrew from the entire northern front, including around Kyiv, Chernihiv, and Sumy. That was turning point number one — the decapitation strike failed completely.
That's when the atrocities in places like Bucha came to light.
When Ukrainian forces retook Bucha, a suburb of Kyiv, they found mass graves and evidence of summary executions of civilians. The UN Human Rights Monitoring Mission has documented over twelve thousand civilian deaths in Ukraine as of late twenty twenty-five, but the actual number is believed to be significantly higher. Bucha was a shock to the international system — it made clear this wasn't just a conventional war between armies.
Phase one fails, Russia pulls back from the north.
Phase two, spring to summer twenty twenty-two, Russia refocused on the Donbas and the south. They made grinding advances — Mariupol fell in May after a brutal siege, Severodonetsk and Lysychansk in June and July. This is when the war shifted to what it's mostly been since: heavy artillery duels, trench lines, incremental gains at enormous cost. Russia would shell a town into rubble, then advance into the ruins. Not fast, not elegant, but they had more artillery and more bodies to throw at the problem.
Then the counteroffensives.
Turning point number two. In September twenty twenty-two, Ukraine launched a surprise counteroffensive in the Kharkiv region. They broke through Russian lines and retook something like six thousand square kilometers of territory in a matter of weeks, including the major rail hub of Kupyansk. The Russian front essentially collapsed in that sector. Then in November, Ukraine retook Kherson — the only regional capital Russia had captured since the invasion began. Russia withdrew from the west bank of the Dnipro River, which was a major strategic and symbolic loss.
That was the high point of Ukrainian momentum, I'd say.
And then things got harder. Through twenty twenty-three, the much-anticipated Ukrainian counteroffensive in the south — aimed at cutting the land bridge to Crimea — didn't achieve its objectives. Russian defensive lines, particularly the Surovikin Line, were incredibly dense: minefields, anti-tank ditches, dragon's teeth, pre-registered artillery. Ukraine made some gains around Robotyne but never came close to Tokmak or Melitopol. That was turning point number three in a negative sense — it demonstrated that breaking prepared Russian defenses without air superiority is extraordinarily difficult.
That's roughly where things have been since? A grinding stalemate?
More or less, with some significant developments. Through twenty twenty-four and into early twenty twenty-six, Russia has been making slow, costly advances in the Donbas — Bakhmut fell in May twenty twenty-three after months of fighting that the Institute for the Study of War described as some of the most intense urban combat since World War Two. Avdiivka fell in February twenty twenty-four. Russia has been pushing toward Pokrovsk and Chasiv Yar. But the gains are measured in kilometers per month, sometimes meters per day, at staggering human cost.
Let's put numbers on that. What does the territorial picture actually look like right now?
According to the Institute for the Study of War, which tracks this daily, Russia currently occupies approximately eighteen to nineteen percent of Ukraine's internationally recognized territory. That includes Crimea, which they seized in twenty fourteen, and the land corridor connecting it to Russia through the Donbas. The front line is about one thousand kilometers long, stretching from the Kherson region in the south, through Zaporizhzhia, through Donetsk and Luhansk, up to the Kharkiv region in the north.
When you say eighteen to nineteen percent, we're talking about something like one hundred ten thousand square kilometers.
To put that in perspective, it's about the size of Bulgaria or the state of Tennessee. But it's important to understand what that territory includes. Russia holds most of Luhansk oblast, about sixty percent of Donetsk, most of Zaporizhzhia's southern strip, and about seventy percent of Kherson oblast — though not Kherson city itself. They've also held Crimea for over a decade now.
What about the territory Ukraine has retaken since the start of the full-scale invasion?
Ukraine has liberated about fifty-four percent of the territory that Russia captured since February twenty twenty-two. But here's the nuance — Russia still holds significantly more Ukrainian territory now than it did before the full-scale invasion, because they held Crimea and parts of Donbas since twenty fourteen. So depending on what baseline you use, the picture looks different. If you count from February twenty twenty-two, Ukraine has clawed back more than half of what Russia took. If you count total Ukrainian territory under Russian occupation, including the twenty fourteen seizures, the number has only gone up since the full invasion started.
That's one of those things where both sides can claim the numbers support them, depending on how you frame it.
And that framing battle is part of the war itself. Russia claims it's defending the Donbas republics and that Crimea is historically Russian. Ukraine insists that all occupied territory, including Crimea, must be returned. Those positions are fundamentally incompatible, which is why a negotiated settlement has been so elusive.
Let's talk about what Daniel mentioned — daily life during all this. It's easy to look at a map with shaded occupation zones and forget that millions of people are living, working, and trying to raise families inside Ukraine right now.
This is one of the most under-covered aspects of the war. According to the UN, about fourteen million Ukrainians have been displaced — roughly six million are refugees abroad, and about eight million are internally displaced within Ukraine. But that still leaves something like twenty-five million people living in government-controlled Ukraine, going about their lives as best they can.
I've seen reporting that in cities like Kyiv, there's a strange duality — cafes are open, people go to work, but air raid sirens are a regular occurrence.
In the western and central parts of the country, daily life has adapted in ways that are hard to imagine from the outside. Businesses operate, schools are open — though many have moved partially or fully online — restaurants serve customers, cultural events happen. But the air raid alerts are constant, and the missile and drone attacks are real. Russia has systematically targeted Ukraine's energy infrastructure. In the winter of twenty twenty-two to twenty twenty-three, they knocked out something like fifty percent of the country's power generation capacity through missile strikes. Ukrainians adapted with generators, power banks, and a kind of grim resilience.
The situation in cities closer to the front?
Kharkiv, which is about thirty kilometers from the Russian border, has been hit relentlessly — glide bombs, missiles, artillery. The city still functions, but it's under constant threat. People in frontline towns like Kupyansk or Chasiv Yar have mostly evacuated. The Donbas cities under Russian occupation, like Donetsk and Mariupol, are in a different category entirely — they're under Russian administration now, with all the repression and economic collapse that entails. Mariupol was essentially destroyed in the siege and has been partially rebuilt, but with Russian settlers brought in and a heavy security presence.
Daniel asked specifically about how much daily life is able to operate. I think the answer is — it depends massively on where you are. A university student in Lviv is having a very different experience from a pensioner in Kherson.
Even within relatively safe areas, the psychological toll is enormous. There was a study from the Kyiv International Institute of Sociology in late twenty twenty-four that found something like forty percent of Ukrainians reported symptoms consistent with PTSD. The economy has contracted significantly — GDP dropped by about twenty-nine percent in twenty twenty-two, though it's been slowly recovering since. Inflation is high, the currency has been under pressure, and the government is running a massive budget deficit that's being covered by international aid.
Which brings us to the sanctions question Daniel raised. He made the point that sanctions haven't stopped the war, and that this might explain why people in Israel are skeptical about sanctions as a tool against Iran.
This is a really important parallel, and I think Daniel's onto something, but we need to be precise about what sanctions have and haven't done. The sanctions regime against Russia is unprecedented in scale — the EU, the US, the UK, Japan, and others have imposed over sixteen thousand individual sanctions on Russian entities and individuals. Russia's central bank reserves, about three hundred billion dollars worth, were frozen. Major banks were cut off from SWIFT. Technology exports, particularly semiconductors and components for military production, have been heavily restricted.
Yet the Russian economy didn't collapse.
It didn't. In twenty twenty-two, Russian GDP contracted by about two point one percent — significant but not catastrophic. In twenty twenty-three, the economy actually grew, driven by massive military spending. The government shifted to a war economy, redirecting resources to defense production. And critically, Russia found workarounds — importing sanctioned goods through third countries like China, Turkey, Kazakhstan, and the UAE. Chinese exports of dual-use goods to Russia have surged. There's a whole gray market in semiconductors rerouted through Central Asia.
The sanctions hurt, but they didn't cripple. Is that the bottom line?
It's more nuanced than that. Sanctions have degraded Russia's ability to produce advanced weapons — they're struggling with precision-guided munitions and have been forced to use older, less accurate systems. Sanctions have limited the modernization of their military. They've caused long-term economic damage by cutting Russia off from Western technology and capital markets. But sanctions have not stopped the war, and they haven't forced a change in Putin's strategic calculus. That's the uncomfortable reality, and I think it's fair to draw lessons from that for the Iran situation.
The Iran parallel is interesting because it's not one to one. Iran's economy is much more isolated than Russia's was pre-invasion. Iran has been under sanctions for decades and has developed an entire parallel economic system to cope. Russia was deeply integrated into global markets and took a much bigger shock.
Russia's sanctions shock was acute — Iran's is chronic. But the broader lesson Daniel seems to be pointing at is that sanctions alone, without a credible military threat or a diplomatic off-ramp, rarely force a state to abandon what it sees as a core security interest. Russia sees Ukraine as a core interest — that's clear from their willingness to absorb enormous casualties and economic damage. Iran sees its nuclear program and its regional proxy network similarly. In both cases, sanctions can constrain and degrade, but they probably can't compel a fundamental strategic reversal.
If we're looking at the war now, May twenty twenty-six, what's the actual battlefield picture? You mentioned Russia making slow gains in the Donbas.
The current situation is that Russia is advancing incrementally in several sectors. They've been pushing west of Avdiivka, toward Pokrovsk, which is a key logistics hub for Ukrainian forces in the Donbas. They're also pressing around Chasiv Yar and in the direction of Kupyansk in the Kharkiv region. But the pace remains extremely slow. We're talking about advances of maybe a few hundred meters on a good day, at a cost of hundreds of casualties. The UK Ministry of Defence estimated in early twenty twenty-six that Russian casualties — killed and wounded — have exceeded seven hundred thousand since February twenty twenty-two. That's an astonishing number.
On the Ukrainian side?
Ukraine doesn't publish official casualty figures, but estimates from various Western intelligence sources put Ukrainian military casualties at somewhere between two hundred fifty thousand and three hundred fifty thousand killed and wounded. Ukraine's challenge is less about territory and more about manpower and sustainability. They're a country of about thirty-eight million people pre-war, compared to Russia's one hundred forty million. The attrition math is not favorable over the long term.
That's the grinding logic that Daniel was talking about — Russia just outlasting international attention and Ukrainian resistance.
There's evidence that's exactly the strategy. The Kremlin's theory of victory seems to be that Western support for Ukraine will eventually fracture — either through political changes in the US and Europe, or through simple fatigue, or through competing crises drawing attention away. We've seen some of that already. US aid packages have faced political delays. European ammunition production has consistently fallen short of targets. The EU promised to deliver one million artillery shells to Ukraine by March twenty twenty-four and missed that target by a wide margin.
What's kept Ukraine in the fight?
One, the resilience of Ukrainian society — people don't want to live under Russian rule, and that's not just a talking point. Two, Western military aid, even if it's been slower than promised. HIMARS rocket systems, ATACMS long-range missiles, Patriot air defense batteries, Storm Shadow cruise missiles, F-sixteen aircraft — these have all made a material difference on the battlefield. Three, Ukrainian innovation — they've built a massive drone industry essentially from scratch, producing everything from cheap FPV attack drones to long-range strike drones that have hit targets deep inside Russia, including oil refineries and air bases.
The drone thing is remarkable. A country under invasion building a domestic arms industry while fighting a war.
It's one of the most significant developments of the conflict. Ukraine went from having almost no domestic drone production in twenty twenty-two to producing over a million FPV drones in twenty twenty-four. They've developed naval drones that have pushed the Russian Black Sea Fleet away from the Ukrainian coast, despite Ukraine not having a conventional navy to speak of. The Russian fleet has essentially been forced to relocate from Sevastopol to Novorossiysk and other ports further east. That's a strategic victory achieved with asymmetric means.
The human cost of all this — you mentioned the casualty figures. What about the civilian side?
The UN Office of the High Commissioner for Human Rights has verified over twelve thousand civilian deaths as of late twenty twenty-five, but they emphasize this is a significant undercount because it only includes cases they've been able to verify. The actual number is likely much higher, especially in places like Mariupol where independent monitoring has been impossible. There's also the less visible toll — the children who've missed years of school, the elderly who couldn't evacuate frontline areas, the families separated by borders and front lines. The psychological and social damage will take generations to repair.
On the Russian side, the occupation has its own grim reality.
The occupation authorities have been systematically erasing Ukrainian identity in the territories they control. Ukrainian language education has been suppressed, curricula have been replaced with Russian state curricula, Ukrainian cultural institutions have been shut down or repurposed. There have been widespread reports of torture, arbitrary detention, and forced disappearances. The UN and Human Rights Watch have documented filtration camps where Ukrainians are screened, interrogated, and sometimes forcibly deported to Russia. The International Criminal Court has issued arrest warrants for Putin and his children's rights commissioner Maria Lvova-Belova over the forced transfer of Ukrainian children to Russia.
Yet, as Daniel pointed out, this war has faded from the front pages.
That's one of the most striking things about it. In February and March twenty twenty-two, Ukraine was the dominant global news story. Now, in May twenty twenty-six, it's competing for attention with the Strait of Hormuz tensions, the Russia-Ukraine ceasefires that just got declared — which, by the way, are competing ceasefires, each side accusing the other of violations — and whatever the latest AI industry drama is. The attention economy is brutal, and long wars suffer in it.
The competing ceasefires thing is worth a moment. That just happened.
Yes, both Russia and Ukraine declared ceasefires in the past few days, but they're not coordinated — they're unilateral declarations with different terms and different timeframes, and both sides are already accusing each other of violations. It's not a peace process, it's a PR move layered on top of continued fighting. This is what a frozen conflict in its early stages looks like — neither side willing to make real concessions, but both wanting to appear reasonable to external audiences.
Which loops back to Daniel's point about the battle calculus. If Russia can keep this simmering indefinitely, they may calculate that Ukraine's international support eventually erodes to the point where Kyiv has to accept territorial concessions.
That's the strategic question that doesn't have a clear answer yet. Will Western support hold? The US has been the largest single donor of military aid to Ukraine, but domestic politics around aid packages have been contentious. European countries are increasing defense spending and ammunition production, but the ramp-up has been slower than Ukraine needs. Meanwhile, Russia has put its economy on a war footing, secured weapons from North Korea and Iran, and is recruiting enough soldiers — through a combination of high pay, coercion, and prison recruitment — to sustain the current tempo of operations.
Where does this leave us? If someone's trying to understand this war at the basic level, like Daniel asked, what's the summary picture?
It's a war that Russia expected to win in days and is now in its fourth year. Russia holds about a fifth of Ukraine's territory, mostly in the east and south. Ukraine has prevented a total defeat, retaken significant ground, and innovated in ways that have changed modern warfare — particularly in drone warfare and asymmetric naval operations. The front line moves slowly, at enormous human cost. Sanctions have constrained Russia but haven't stopped the war. International attention has waned even as the fighting continues. And there's no clear path to a resolution because both sides' minimum demands are incompatible — Ukraine insists on territorial integrity including Crimea, Russia insists on keeping what it's taken.
The daily life piece — for millions of Ukrainians, this is just reality now. They've adapted to air raid sirens and power outages the way people adapt to anything. Humans are remarkably good at normalizing the abnormal.
That's both inspiring and tragic. You see it in the photos from Kyiv — people sitting in cafes, going to concerts, living their lives, while somewhere in the Donbas, soldiers are in trenches and civilians are sheltering in basements. The war has created two completely different experiences of Ukraine depending on geography. And the longer it goes on, the harder it becomes to bridge those experiences back together whenever it eventually ends.
Daniel also mentioned the absence of a strong international response beyond sanctions. I think that's worth poking at a bit more. Because it's not that the response has been nothing — the military aid has been substantial, the diplomatic isolation of Russia has been real. But there's been no direct military intervention, no enforcement of a no-fly zone, nothing that would risk direct NATO-Russia conflict.
That's been a deliberate choice by NATO countries since day one. The Biden administration, and now the current administration, have been consistent about this — they will support Ukraine with weapons, intelligence, training, and money, but they will not put American or NATO troops in direct combat with Russian forces. The fear of escalation to a nuclear exchange has been the unspoken constraint on everything. Whether that constraint is wise or excessive is a debate in itself, but it's been the defining limit on the international response.
Which, again, is something people in Israel watch closely. If a country facing an existential threat can't count on direct intervention, only on weapons and sanctions, that shapes how you think about self-reliance.
The Ukrainian experience has reinforced the Israeli strategic doctrine that ultimately, a country has to be able to defend itself by itself. Allies can help, but they have their own red lines and their own domestic politics. That's not cynicism — it's just reading the evidence of the past four years.
One last thing before we wrap the core discussion. You mentioned the ISW tracking territorial control. How reliable is that data at this point?
The Institute for the Study of War produces what's probably the gold standard for open source conflict mapping. They use geolocated imagery, official statements from both sides, and a network of sources on the ground. It's not perfect — there are always lags between events on the ground and confirmed assessments — but it's the best publicly available picture. Their daily updates show territorial control at a granular level, and they've been doing this consistently since the invasion began. It's a remarkable analytical product, and it's one of the reasons this war is the most transparently documented major conflict in history.
Because of the OSINT ecosystem Daniel was talking about.
Satellites, drones, social media, open source analysts — you can watch this war unfold in near real time from your living room. That's historically unprecedented, and it's changed both how wars are fought and how they're understood by the public.
Let's do Hilbert's fun fact and then wrap this up.
And now: Hilbert's daily fun fact.
Hilbert: The banana slug, native to the Pacific Northwest, has a penis that is roughly the same length as its entire body — up to eight inches — and after mating, it sometimes chews off its partner's organ to prevent them from mating again.
an evolutionary strategy, I suppose.
I have no follow-up questions.
This has been My Weird Prompts. Thanks to our producer Hilbert Flumingtop. If you enjoyed this, we'd appreciate a review wherever you listen. You can find every episode at myweirdprompts.
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