When Has Putin’s Invasion Failed?

And now for something completely different.

Ukrainian resistance to the Russian invasion had been much stronger than anyone was expecting. Captured documents say the Russian military was expecting this invasion to take about two weeks, and unless the Russians have a really good couple of days ahead of them, that isn’t panning out. But also, blitzing a nation the size of Ukraine in two weeks was delusionally hubristic in the first place. There’s still plenty of room for the Russian blitz to succeed by the standards of actual blitzkriegs that have happened in the real world even despite the imminent failure to live up to their own fantasies. On the other hand, Ukrainians aren’t exactly giving ground quickly. So if we don’t pop the champagne yet, when do we? When has Ukraine officially resisted Russian invasion long enough that we can say this has turned from a blitz to a slog?

Before getting into dates, let’s talk about what “resisting Russian invasion” means. Ukraine has resisted Russian invasion so long as they have conventional forces which are still meaningfully engaged in defending Ukrainian cities and territory from a Russian advance. If Russia successfully captures all Ukrainian territory but then gets bogged down in guerilla war for ten years before giving up and going home, then that means the Russian invasion succeeded but the Russian occupation failed. The reason for this distinction is that it wouldn’t even be particularly surprising if Ukraine held out against a Russian occupation and eventually forced them to go home after years of quagmire. That happens all the time. What’s potentially surprising is if Ukrainian conventional forces remain intact and continue to hold ground against Putin’s invasion longer than middle powers have held out against world-class militaries in the past, as that would indicate that Russia’s military is not, in fact, world-class, despite its might on paper.

The main cities to watch with regards to whether Ukraine is holding against the invasion are:

-Kyiv, which obviously holds extreme political and cultural significance.
-Kharkiv, which is strategically important to Ukraine’s ability to contest the Donbass region.
-Mariupol, which is strategically important to Ukraine’s ability to contest the Donbass region and control of the Black Sea.
-Kherson, which is somewhat important to control of the Black Sea, but mainly important because of its control of a nearby canal leading to Crimea, without which Crimea’s population capacity is drastically reduced. Ukraine blocked up this canal in 2014 after the occupation of Crimea, and Crimea has been steadily drying out ever since.
-Odessa, which is important to control of the Black Sea.
-Lviv, which sits near the Polish border and could potentially end up being a final stronghold in the west (though there have been rumors that an invasion from Belarus might try to capture it much earlier, in an effort to cut off NATO support to Kyiv). This one is potentially unnecessary for Russia to declare victory, however, if they capture the eastern half of the country and just decide to stop. If Ukrainian counterattacks out of Lviv are unable to recapture any of the other five cities and Russia doesn’t even try to capture Lviv (or push west of Odessa and Kyiv in general), then it would be fair to say that the Russian invasion has succeeded in capturing eastern Ukraine. Part of successful military operations is keeping your objectives within your capabilities, after all.
-For completenesses’ sake I’ll also add Luhansk, Donetsk, and Simferopol, because they’re cities which were in Russian hands even before the invasion, so if Ukraine ends up in control of them, we can safely say the blitzkrieg has failed because a Ukrainian counterattack has succeeded beyond the most outlandish of expectations. Honestly, this is so unlikely that I’m pretty sure it’s mostly just my game designer instincts treating this like a scoreboard, where the system should be prepared to handle a very successful Ukrainian counterattack no matter how unlikely that seems.

It’s also important to note that, while it is important to keep fog of war in mind (nobody’s figures concerning casualties, material captured/destroyed, etc. etc. should be trusted), fog of war has never been able to obscure where the front lines are and will not be able to do so for the foreseeable future. Anyone claiming that we can’t even know for sure whether these cities have been captured is either getting lost in the reeds of what exactly it means to “capture” a city or else is repeating cautions about fog of war that they’ve heard from other, smarter people, which they have misinterpreted to mean “we literally can’t know anything about how the war is going.” The reason why I’m emphasizing who controls what cities is because that is very visible even through fog of war. With modern communication technologies, we should expect to know when a city has changed hands within 24 hours (and indeed, when Kherson fell, we know about it pretty much immediately).

So what about dates?

EDIT: It recently occurred to me that I should look at Japanese invasions during WW2 as well, since they also rapidly conquered a bunch of territory in a modern war. I’ve added those in to the list of dates below. I don’t want to make a new post about it, since this isn’t supposed to be a political blog, so instead I’m just slipping in a stealth update.

Dates

The Japanese invasion of Thailand lasted all of one day and Ukraine successfully outlasted it as of February 26th. Thailand signed a treaty long before all of their territory had been taken, which also applies to French Indochina and Yugoslavia further down.

The Japanese invasion of Guam lasted 3 days. Ukraine successfully outlasted it as of February 28th. Guam, along with the Netherlands, Belgium, Wake Island, Hong Kong, and Singapore, further down, are all very small countries, which makes them very easy to blitz because there is less territory to take before you’re done.

The Japanese invasion of French Indochina lasted 4 days. Ukraine successfully outlasted it as of March 1st.

The German blitzkrieg of the Netherlands and the Japanese invasion of Singapore both lasted 7 days. Ukraine successfully outlasted them as of March 4th.

The German blitzkrieg of Yugoslavia lasted 12 days. Ukraine successfully outlasted it on March 9th (the date of writing). It’s worth noting that a major reason why this particular blitz went so quickly is because Yugoslavia signed an armistice.

Initial Russian expectations for the invasion of Ukraine were that it would take 15 days, which is how long the Japanese invasion of Wake Island took. Ukraine will have successfully outlasted it on March 12th. As can be seen from the rest of the dates on this list, this would have been a ludicrously fast blitz for a nation the size of Ukraine.

The Japanese invasion of Hong Kong lasted 17 days. Ukraine will have successfully outlasted them on March 14th. Hong Kong is a single city, so the apples-to-apples comparison here is Kyiv, specifically, not all of Ukraine. The same applies to Baghdad further down.

The German blitzkrieg of Belgium lasted 18 days. Ukraine will have successfully outlasted it on March 15th.

The American invasion of Iraq captured Baghdad after 21 days. Ukraine will have successfully outlasted it on March 18th. It’s worth noting that Baghdad was over 300 miles from the initial frontlines of the invasion and did not fall under attack until about two weeks in, whereas Kyiv is less than 100 miles from the Belarussian border and fell under attack within the first day or two. Measured from time since the start of the battle, Kyiv-against-Russia outlasted Baghdad-against-America on March 3rd.

The German blitzkrieg of mainland Greece (but not Crete) lasted 25 days. Ukraine will have successfully outlasted it on March 22nd.

The German blitzkrieg of Poland lasted 35 days. Ukraine will have successfully outlasted it on April 1st (yes, really). From this point, we start getting into standard blitzkrieg length, where Ukrainian resistance will be starting to outlast what a reasonable person might have expected from a world-class military attacking a sizable but much weaker neighbor.

The American invasion of Iraq up to the official cessation of “major combat operations” lasted 43 days. Ukraine will have outlasted it on April 8th.

The German blitzkrieg of France and the low countries (including Belgium and the Netherlands) lasted 46 days. Ukraine will have outlasted it on April 11th.

The complete German blitzkrieg of the Balkans, including Yugoslavia, mainland Greece, and Crete, lasted 57 days. Ukraine will have outlasted it on April 23rd.

The German blitzkrieg of Norway lasted 62 days. Ukraine will have outlasted it on April 28th. Norway held out against German blitzkrieg longer than any nation except Britain and Russia, where the blitzkrieg failed entirely. The remaining dates on the list discuss invasions either of extremely defensible nations (which Ukraine is very much not), amphibious invasions, or invasions which not only failed to capture the target country quickly, but failed completely. If Ukrainian resistance lasts this long (and it’s not clearly on its last legs when it gets here), then it will be reasonable to say that Ukraine is actually more likely to win than lose even in the conventional stage of the war (although even then, 50.1% odds of victory is very different from an inevitability).

The Japanese invasion of Malaya lasted 69 days (yes, really). Ukraine will have outlasted it on May 5th. Many of these Japanese invasions last longer than the European invasions the Nazis conducted, yet still ended in victory for Japan. It is worth noting, however, that these were naval invasions with very long supply lines being compared to land invasions against nations on Germany’s doorstep (and the two nations Germany attempted to blitz from across the sea, Norway and the UK, both held out longer than the land invasions – in the UK’s case, they won entirely).

The American invasion of Afghanistan lasted 71 days. Ukraine will have outlasted it on May 7th. It’s worth noting that Afghanistan is a particularly hard country to invade because of its terrain, and Ukraine is very much the opposite. Additionally, a very rapid invasion of Afghanistan was a political necessity that meant America had relatively little time to prepare the invasion (less than a month!), whereas Putin had time to build up his invasion forces before attacking Ukraine (which makes his invasion more comparable to the American invasion of Iraq than Afghanistan).

The Japanese invasion of the Dutch East Indies lasted 91 days. Ukraine will have outlasted it on May 26th.

The Japanese invasion of Borneo lasted 106 days. Ukraine will have outlasted it on June 11th. It’s worth noting that the line between the conventional war in Borneo and a guerilla war (conducted by Allied soldiers, but still) is pretty blurry and it’s hard to say when exactly the invasion had ended. I’m giving it the full 106 days, but you could make arguments that the invasion was much faster and it was the occupation that took 106 days (total) to quash resistance.

As the British count it, the Battle of Britain – Germany’s failed blitzkrieg of the UK – lasted 112 days. Ukraine will have outlasted it on June 17th. The British count the Battle of Britain as the period of most intense bombing. For purposes of how long the attempted blitzkrieg of the UK was, this is probably a better answer than the German one (given below). After this point, while Germany and Britain were still at war, the blitzkrieg can be safely said to have failed.

The Japanese invasion of Burma lasted 125 days. Ukraine will have outlasted it on June 30th.

The Japanese invasion of Philippines lasted 151 days. Ukraine will have outlasted it on July 26th.

The Japanese invasion of Manchuria lasted 162 days. Ukraine will have outlasted it on August 6th. This is an outlier compared to the other invasions on this list, as it was successful, non-amphibious, the target did not have exceptionally defensible terrain, and the invasion took over five months. Regardless of general trends, wars do not come with time limits. Ukraine does not automatically win when the calendar ticks over to May or June or whenever.

Operation Barbarossa – Germany’s failed blitzkrieg of Russia – lasted 167 days. Ukraine will have outlasted it on August 11th. This will be particularly significant because while Operation Barbarossa failed to capture the entire Soviet Union, it successfully went from one end of Ukraine to the other.

As the Germans count it, the Battle of Britain – Germany’s failed blitzkrieg of the UK – lasted 308 days. Ukraine will have outlasted it on December 30th. The Germans count the Battle of Britain starting from more or less the same date as the British, but extend it until bomber units were withdrawn in mid-May to be repositioned east in preparation for Operation Barbarossa. This makes sense from a general historical perspective, but is a bad way of measuring how long the attempted blitzkrieg of the UK lasted. If Ukraine finally capitulates in December, we’ll hardly be calling it a lightning campaign.

The entire German invasion of Russia, from the beginning of Operation Barbarossa until the Nazis were pushed out of Soviet territory completely, is hard to quantify. The Soviet eviction of Nazi invaders bled directly into their counterattack into Eastern Europe and ultimately the German homeland. Picking a somewhat arbitrary date of August 30th, 1944, the entire invasion of Russia lasted 1154 days. Ukraine will have outlasted it on April 24th, 2025.

The Japanese invasion of the Solomon Islands ultimately failed. It lasted 1306 days. Ukraine will have outlasted it on September 22, of 2025. I add this one in because the invasion of the Solomons is an example of a conventional campaign targeting a medium-size country in which the invasion never succeeded and (unlike the invasion of the Soviet Union) there is a clear boundary when the invaders were defeated in that country that did not require the invaders’ homeland to be conquered. It’s not a perfect analogy, but given the paucity of data for conventional wars fought with even somewhat modern technology, it’s not a terrible yardstick for how long a war can drag on.

Conclusion

Given an invasion starting February 24th, we would expect Ukraine to last until sometime in April. If Ukraine falls in March, that would still represent a relatively quick invasion even by the standards of blitzkrieg, despite also being slower than the insane timetable Russian generals gave their soldiers. If Ukraine falls in April, that’s about what we’d expect from a world-class military invading a sizable but much weaker neighbor. If Ukraine makes it to May, Putin has good reason to be nervous that the invasion might fail completely. Most attempted blitzkriegs that lasted that long were either amphibious invasions or ended in total failure. If Ukrainian resistance lasts until August, Putin’s attempt at a rapid conquest has failed by definition, even if he continues pouring blood and treasure into a long war.

I’ve been very confident that Putin will fail to achieve his war goals within the next few days, as his original timetable called for. The war is just clearly not moving that fast. The future gets harder to predict very fast as we move weeks or especially months ahead. I have no idea how likely any of the outcomes I’ve described in this post are. My goal here isn’t to make claims about how the conflict is going to go, but to hopefully help people see the forest for the trees. Everyone’s been so taken aback that Ukraine stands a chance and now many people are overcorrecting and act as though it’s Putin whose defeat is inevitable, but as of right now the advantage in manpower and material has given the invaders the upper hand despite a few blunders in the opening attack.