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Aside from the Soviet failure to see the German invasion in the east and Pearl Harbor in the Pacific - the latter I don't want to get into because I don't want the conversation to devolve into Roosevelt conspiracy theories - what was worse, Montgomery's failure to note the deployment of Panzer divisions around Arnhem or the failure to detect the German's Ardennes offensive, or something that I've missed all together?
The pending Operation Barbarossa was detected, the problem there wasn't absence of awareness, it was Stalin's refusal to accept the reality.
Some that might qualify.
1) The German failure to detect that their Enigma coding process had been compromised early in the war.
2) The Japanese failure to detect that their diplomatic and later military codes had been compromised even before the war. More than a year after the Midway victory which had been made possible by reading the Japanese codes, the same trick was used to set up the assassination of Admiral Yamamoto.
3) 100% of the spies sent to England by Germany starting in the fall of 1940 were identified by M15 and either placed in detention or turned into double agents on behalf of Great Britain. Abwehr was 0 for however many agents they sent.
The Japanese failure to detect that their diplomatic and later military codes had been compromised even before the war. More than a year after the Midway victory which had been made possible by reading the Japanese codes, the same trick was used to set up the assassination of Admiral Yamamoto.
A meaningless quibble, really, but it was a little less than a year later (June 4, 1942 to April 18, 1943).
My vote for one of the biggest "oops!" was the French relying on the Maginot line to keep out the Germans, as well as how the Germans faked them out to think they would invade from the north, in a full frontal assault over open ground, because of Maginot.
The Battle of the Bulge comes to mind immediately.
The failure of MacArthur to react/prepare in the Phillipines immediately after the attack on Pearl Hiarbor.
The continuing downplaying, for a couple years maybe, of the actual competence of Japanese aviators and the actual capabilities of some of their aircraft (all Japanese had poor eyesight and the planes were made of bamboo and rice paper).
This. Britain surrendering Singapore despite having a superior numbers, and a defensible position.
What would that defensive position have been, a coastal city with their backs to the ocean and opposing army approaching on two sides and zero hope of resupply. Makes Bataan seem like a walk in the park.
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