Factual error: The Germans in the castle are using Bell 47 helicopters which, apart from being manufactured by the enemy, did not even appear until after the war.
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The idea of helicopters was not necessarily new in WW2, but effective designs were not made until after the war; there is evidence from some literary sources (one of them being a book named "German Secret Weapons of WW2" or something like that) that the Germans did indeed conduct experiments and designs on this vehicle type. See more...
Where Eagles Dare (1968) - 3 major mistakes
starring Clint Eastwood, Richard Burton (add more)
Factual error: In the courtyard of the castle there is an anti-aircraft gun. You could probably not find a worse place for a gun like that even if you tried (except maybe if you put it inside, in a windowless room). In the position it is placed it can only fire at targets directly ABOVE the castle. What you want to do is fire at targets BEFORE they reach the castle. It would be better if they placed it on the roof, or even near the village below.
Continuity: When Smith is driving the bus, there are at one point several bullet holes in the bus' windscreen and in the next shot they have vanished.
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