I from a crypto history book I read in high school: in WWI, German intercepts of Russian transmissions have the Russians illusions of German tactical genius. Somehow, Germans would often be in position to confound the Russians. The reason for this: Russian code clerks were badly trained. Sometimes there would be a couple of attempts to send a message followed by a plain-text transmission by the frustrated code clerk.…
There was one story of an Afrika corp operator who sent HIT - LER as the 2 'secret' triplets every day for the entire North Africa campaign. Then disastrously he was captured!
It's an interesting question as to whether at least the best (4-wheel naval) system could be cracked without operator error or deliberate plain text seeding.
The only flaw of the enigma is that a letter cannot be encrypted to itself - I have heard different accounts of if this was enough to always make it crackable.