WI: Finland won the Winter War?

Finland did win the Winter War, it got pretty much the best result realistically possible when it had to fight the USSR alone. To get an even better result, you would need to avoid the war altogether.
 
What if, somehow, the winter war was even worse for the Russians? What if Finland was able to win the Winter War?
Not really possible given the size and power difference between the two. OTL Finland was stretched pretty much to the limit from my understanding just holding out for as long as it did. Stalin isn’t going to take a black eye, shrug, and go ”Ok, guess you got me, time to go home”. Accepting a Finnish win is just too big of a prestige hit.
 
The Finns might have been able to win in March with a better supply of artillery and ammunition. Considering the numerical disparity, this may have been one of the most important considerations. If Stalin isn't satisfied with the results of the March offensive, the Soviets really can't do anything until June, after France has fallen. I don't know if that would make a difference for Stalin, but a longer war could have important impacts on Finland's diplomatic situation, like an Anglo-French intervention in spring.
 
The Finns might have been able to win in March with a better supply of artillery and ammunition. Considering the numerical disparity, this may have been one of the most important considerations. If Stalin isn't satisfied with the results of the March offensive, the Soviets really can't do anything until June, after France has fallen. I don't know if that would make a difference for Stalin, but a longer war could have important impacts on Finland's diplomatic situation, like an Anglo-French intervention in spring.
The available Finnish trained manpower was running low - at the beginning of the war the
Finns had deployed 130 000 men to the Isthmus, 40 000 North of Laatokka, and couple of thousand in total to the rest of the border streching from Ilomantsi to Petsamo.

By the end of the war the Finnish frontline strength at the Isthmus was 50 000 - 20 000(!).
The manpower that enabled Finnish army to mobilize c. 500 000 citizens out of a population of 3,7 million by 1944 was mostly there.

But in spring 1940 they lacked weapons and, most importantly, training.
 
Not really possible without a German victory of some sort on the Eastern Front. To Finland's credit I think they got the best possible result considering the odds and the circumstances. Simply existing and continuing to exist is a win, just ask the Soviets at the time.
 
There's an old timeline that's sporadically updated these days that's about if Finland had done it's best to prepare for a war with Russia after independence.
https://www.alternatehistory.com/forum/threads/what-if-finland-had-been-prepared-for-the-winter-war.185434/
You can check it out. It's a good read, even if it's a lot of text.
While CanKiwi's timeline has been well researched, in my opinion it still suffers from couple of problems.
First, as you mentioned, the update schedule is sporadic at best.
Second, while there's plenty of well-researched background, the main timeline has not reached the actual war apart from few snippets.
And third, it really is something of a Finland-wank. I mean the timeline sees Finland possessing an air force over a thousand aircraft before the war, deployment of veritable Wunderwaffen like infrared equipment, guided bombs and body armor to name a few. Looking at the equipment, the timeline wanks the FDF to the 1950's, if not the 1960s. This combined with the building of a military-industrial complex thats able to supply to greatly boosted Finnish forces for the Winter War (which lasts more than nine months) to fight the Soviet Union. As for manpower reserves, I don't even know...
Judging by the table of contents that has been presented, the Finland does a deus ex machina by effectively wrecking the Soviet Navy and merchant marine early in the war, destroying much of the Soviet air force and aircraft industry and the Finnish Army holds off the Red Army indefinitely with one of the major battles occuring in the area of Tali-Ihantala because of course it does, with the war ending with Finnish Air Force strike on Kremlin killing Stalin and allowing other people to take charge and seek peace with Finland.
 
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