While reading up on the cryptology profession, I noted some particularly facepalm-worthy things that made me laugh hard at the sheer fail, and since I've always considered history to be a rich mine of comedy, here are some of my favorite moments of utter fail in the cryptological arena of human history.
Battle of Tannenburg - World War I was a pretty dumb war because everyone in it was fighting for some really narrow-minded objectives that clashed hard with reality, with the Russians having a reason that amounted to an alliance with France they should have ignored and a hurt ego they wanted to assauge, but they fought anyway and we got the USSR in replacement of the Tsars.
In cryptology, they screwed up this major battle hard because they were lazy and sent messages in cleartext even though it was no secret the Germans were not ashamed to read other people's mail and this entire battle was an utter failure on their part because the Germans knew exactly what they were doing and where.
The loss didn't knock them out of the war, but it was their most embarrassing defeat and set the tone for their eventual and permanent quitting of WWI.
The "Petit Chiffre" - Napolean was considered a brilliant general, but oddly, he was one of the few people in his entire armed forces who knew squat about communications security, and he used a nomenclature style cipher called the "Petit Chiffre" or "little cipher". It had crap security (nomenclatures typically were easy to crack), but it was genius compared to how most of his sub-commanders were apparent morons who didn't like to bother with such things.
It served his Grand Armee poorly while he tried to invade Russia and played a huge role in his humiliating defeat, mostly because his commanders were paste eaters who couldn't read ciphers very well and were often too stupid and lazy to bother.
The Great Cipher - Ironically, while another French example of crypto fail, the cipher itself, invented by Antonie Rossignol, was a good one. It was one of the few nomenclature style ciphers that held up so well it was pretty effective at concealing French missives to the point it had to be cracked by hand in the late 1800's by Etienne Bazeries over the course of three years so the French could read most of the enciphered material it had once covered.
The fail comes from the fact Rossignol was the only guy (and his family) who knew how it worked. Most nomenclature ciphers were a mix of a cipher alphabet that was a substitution of different letters for a standard set of letters and a bunch of code terms, usually listed in sequence.
Rossignol wisely changed up the cipher alphabet to a syllabary style cipher (which confused most analysis of ciphers for centuries) and listed code terms out of alphabetical order with various different names in place of obvious terms to further baffle people.
While it was very effective, once Rossignol and his heirs died, it fell out of use and the instructions died with them, leaving most French archives in cipher from Louis XIV to 1811 utter gibberish no one could read. Apparently, while secure, Rossignol's instructions on how to use it were never properly recorded for future generations and the French had to wait until Bazeries worked backward over three years in the 1890's to figure out how it worked once more.
Enigma - Also known as the cipher machine that lost WWII for the Nazis. The reason this was utter failure is due to a bunch of technical details that had doomed it since not long after it's creation.
Enigma was a rotor-based, electromechanical enciphering machine, and it had been used for commercial purposes before the Nazis snapped it up as their chief enciphering machines for military purposes. While they thought it was secure, it had several weaknesses that made it's security a laughable joke.
1. While it went through several improvements, the underlying basic mechanical principles of the machine dated back to the 1920s and the Commerical and military-specific models all shared these factors in common.
2. Rotors were much faster than humans at encipherment, but their principles could still be followed mathematically by any reasonably competent arithmetician with a decent knowledge of how the mechanical aspects of the Enigma used math to randomize the security keys.
3. Before the Nazis took it off the market, various other nations forked their own version based off the open-source blueprints of the commercial versions and had a good idea how it worked on a basic level, and when they realized a lot of German missives used Enigma, this gave them a good starting place for uncovering it's cipher shields.
As a result of these factors, the British with Polish help made a frail joke of Enigma and were consistently reading the Germans mail through most of the war.
Zimmerman Telegram - During World War I, the brainlets behind the German war machine very stupidly signed off on a plan that would draw the United States into a conflict it had tried to remain officially neutral on because they wanted to practice unrestricted submarine warfare and couldn't unless they risked US intervention.
So the German ambassador who was guilty of trying to egg Mexico into a war with the US was authorized to try convincing Mexico to go to war with the US to keep the US distracted while the Germans sunk everything they could shoot in the Atlantic, with or without Americans aboard just so they could have naval superiority.
The plan had three big flaws.
1. Mexico was wise enough to realize this was utter idiocy. The last time they fought the US, they got demolished, and when the US withdrew it's forces from Mexico (where they had been pursuing a guy named Pancho Villa who they and the current Mexican leadership wanted with his head on a pike) shortly prior because the US help was wearing out it's welcome, they had no reason to start anything with the US and told the Germans to shove it.
2. The Germans pretended to openly consider the US a potential neutral party for possible peace negotiations up until this little plot came out, and they destroyed any and all good-faith the US had assumed of them when Arthur Zimmerman admitted he was the author of the decrypted telegram that the British intercepted that had him spell out his scheme for getting Mexico onboard with the German war effort.
3. The Germans practiced stupid cipher security. They sent the Zimmerman telegram via two separate channels, one in a rather hard to crack cipher, one that was older and had security flaws, and the British found the weaker of the two, compared it to the other one, and managed to piece together the unencrypted version based on their notes on both ciphers. Because of this laziness, the British provided the US with an intelligence bombshell and President Woodrow Wilson had a perfect causus belli for declaring war on Germany.
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