Classical Cryptosystems

Read this section on classical cryptosystems. Pay attention to the substitution cipher, the Vigenere cipher, and the Enigma cipher. As you read, consider these study questions: Who was the Vigenere cipher named after, and who first cracked the Vigenere cipher? Who cracked the Enigma cipher, and what repeated phrase at the end of every message helped to break the cipher? What is perfect secrecy?

A great many cryptosystems have been devised and broken throughout the ages. Let us recount just some of these stories. In 1587, Mary the queen of Scots, and the heir to the throne of England, wanted to arrange the assassination of her cousin, queen Elisabeth I of England, so that she could ascend to the throne and finally escape the house arrest under which she had been for the last 18 years. As part of this complicated plot, she sent a coded letter to Sir Anthony Babington.


Figure 21.1: Snippet from encrypted communication between queen Mary and Sir Babington

Mary used what's known as a substitution cipher where each letter is transformed into a different obscure symbol (see Figure 21.1). At a first look, such a letter might seem rather inscrutable- a meaningless sequence of strange symbols. However, after some thought, one might recognize that these symbols repeat several times and moreover that different symbols repeat with different frequencies. Now it doesn't take a large leap of faith to assume that perhaps each symbol corresponds to a different letter and the more frequent symbols correspond to letters that occur in the alphabet with higher frequency. From this observation, there is a short gap to completely breaking the cipher, which was in fact done by queen Elisabeth's spies who used the decoded letters to learn of all the co-conspirators and to convict queen Mary of treason, a crime for which she was executed. Trusting in superficial security measures (such as using "inscrutable" symbols) is a trap that users of cryptography have been falling into again and again over the years. (As in many things, this is the subject of a great XKCD cartoon, see Figure 21.2.)


Figure 21.2: XKCD's take on the added security of using uncommon symbols

The Vigenère cipher is named after Blaise de Vigenère who described it in a book in 1586 (though it was invented earlier by Bellaso). The idea is to use a collection of substitution cyphers - if there are n n different ciphers then the first letter of the plaintext is encoded with the first cipher, the second with the second cipher, the n^{th} with the n^{th} cipher, and then the n+1^{st} letter is again encoded with the first cipher. The key is usually a word or a phrase of n letters, and the i^{th} substitution cipher is obtained by shifting each letter k_i positions in the alphabet. This "flattens" the frequencies and makes it much harder to do frequency analysis, which is why this cipher was considered "unbreakable" for 300+ years and got the nickname "le chiffre indéchiffrable" ("the unbreakable cipher"). Nevertheless, Charles Babbage cracked the Vigenère cipher in 1854 (though he did not publish it). In 1863 Friedrich Kasiski broke the cipher and published the result. The idea is that once you guess the length of the cipher, you can reduce the task to breaking a simple substitution cipher which can be done via frequency analysis (can you see why?). Confederate generals used Vigenère regularly during the civil war, and their messages were routinely cryptanalzed by Union officers.

Figure 21.3: Confederate Cipher Disk for implementing the Vigenère cipher


Figure 21.4: Confederate encryption of the message "Gen'l Pemberton: You can expect no help from this side of the river. Let Gen'l Johnston know, if possible, when you can attack the same point on the enemy's lines. Inform me also and I will endeavor to make a diversion. I have sent some caps. I subjoin a despatch from General Johnston."


The Enigma cipher was a mechanical cipher (looking like a typewriter, see Figure 21.5) where each letter typed would get mapped into a different letter depending on the (rather complicated) key and current state of the machine which had several rotors that rotated at different paces. An identically wired machine at the other end could be used to decrypt. Just as many ciphers in history, this has also been believed by the Germans to be "impossible to break" and even quite late in the war they refused to believe it was broken despite mounting evidence to that effect. (In fact, some German generals refused to believe it was broken even after the war.) Breaking Enigma was an heroic effort which was initiated by the Poles and then completed by the British at Bletchley Park, with Alan Turing (of the Turing machines) playing a key role. As part of this effort the Brits built arguably the world's first large scale mechanical computation devices (though they looked more similar to washing machines than to iPhones). They were also helped along the way by some quirks and errors of the German operators. For example, the fact that their messages ended with "Heil Hitler" turned out to be quite useful.


Figure 21.5: In the Enigma mechanical cipher the secret key would be the settings of the rotors and internal wires. As the operator types up their message, the encrypted version appeared in the display area above, and the internal state of the cipher was updated (and so typing the same letter twice would generally result in two different letters output). Decrypting follows the same process: if the sender and receiver are using the same key then typing the ciphertext would result in the plaintext appearing in the display.

Here is one entertaining anecdote: the Enigma machine would never map a letter to itself. In March 1941, Mavis Batey, a cryptanalyst at Bletchley Park received a very long message that she tried to decrypt. She then noticed a curious property– the message did  not contain the letter "L". She realized that the probability that no "L"'s appeared in the message is too small for this to happen by chance. Hence she surmised that the original message must have been composed only of L's. That is, it must have been the case that the operator, perhaps to test the machine, have simply sent out a message where he repeatedly pressed the letter "L". This observation helped her decode the next message, which helped inform of a planned Italian attack and secure a resounding British victory in what became known as "the Battle of Cape Matapan". Mavis also helped break another Enigma machine. Using the information she provided, the Brits were able to feed the Germans with the false information that the main allied invasion would take place in Pas de Calais rather than on Normandy.

In the words of General Eisenhower, the intelligence from Bletchley Park was of "priceless value". It made a huge difference for the Allied war effort, thereby shortening World War II and saving millions of lives.

Source: Boaz Barak,
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Last modified: Thursday, April 15, 2021, 2:57 PM