Cryptographic history can be viewed as a running battle between the code makers and the code breakers, and as Part I concluded, the code makers were winning. The polyalphabetic Vigenère cipher proved impregnable for 300 years. In the mid 19th century a British dentist and amateur crytographer, ignorant of cryptographic history, independently reinvented the cipher and issued a public challenge to break it. This annoyed Charles Babbage sufficiently to do so.

Babbage, an all-around great scientist who invented the “difference engine,” a forerunner of the modern computer, used to solve the ciphers in the newspapers’ “agony columns” for fun, which possibly inspired him to the wisest remark in the history of cryptography: “very few ciphers are worth the trouble of unravelling them.” To solve the Vigenère cipher he employed no arcane mathematics, just common sense. He reasoned that the Vigenère cipher is simply a series of monoalphabetic substitution ciphers, repeating every n letters, n being the length of the keyword. The first question is, how long is the keyword?

Babbage looked for repeating sequences in the ciphertext, reasoning that the distance between these sequences will be a multiple of the length of the keyword; i.e., that these sequences encipher the same plaintext. If, say, a four-letter sequence shows up twice in a Vigenère ciphertext, the probability that it represents two different plaintexts is vanishingly small. Babbage then counted the number of letters between the various repeated sequences, and solved for the common factors. Suppose you have a ciphertext with a four-letter sequence repeated 98 letters apart, and a five-letter sequence repeated 35 letters apart. The keyword will be seven letters long.

Once you find the length of the keyword, you’ve reduced the problem to solving seven separate monoalphabetic substitution ciphers. You resort to standard frequency analysis, and you’re done. Babbage essentially decomposed the problem, breaking it into two separately manageable chunks.

All of this time the code makers had not stood still. They developed more and more difficult polyalphabetic ciphers, culminating in Arthur Scherbius’ invention in 1918 of the notorious Enigma machine. Enigma was essentially a triple-shifting device; here’s a partial schematic:

Enigma schematic

The input device was a typewriter keyboard; the output device was a lampboard of the alphabet above it. Each of three rotors, or scramblers, acted as a monoalphabetic substitution cipher. When the operator typed a letter, it would pass through a first scrambler, which would shift it according to its setting, and then rotate one place. The second scrambler would shift it again, and rotate one place itself, after the first scrambler had made a complete rotation of 26 places. Same deal with the third scrambler. Finally the letter would be bounced off a reflector, pass back through the three rotors in reverse order, and the ciphertext — or plaintext, if you were decrypting — letter would light up on the lampboard. To compound the nastiness, the machine included a plugboard, which allowed arbitrary pairs of letters to be swapped before entering the three scramblers. The key consisted of the plugboard settings, the order of the three scramblers, and their initial settings.

Everyone knows that Enigma was broken by British cryptographers, principally Alan Turing, at Bletchley Park during the Second World War. Everyone is wrong. It was actually a Polish cryptographer, Marian Rejewski, who broke Enigma in 1932. The math is too complicated to go into here (Simon Singh provides a lucid description) but Rejewski found a very clever way to separate the effect of the plugboard from the effect of the scrambler, decomposing the problem, just as Babbage had before him. He also relied on cribs, an essential tool of the cryptographer. A crib is boilerplate plaintext that a cryptographer can expect to find somewhere in a message. Computer file headers, dates and times, and names are all excellent cribs. Rejewski’s crib was the fact that the Germans, when transmitting the daily key, would repeat it to deal with possible radio interference. This, and his genius, were enough for him to break Enigma.

This is not to slight the achievements of Alan Turing and his Bletchley colleagues. The Germans eventually stopped transmitting the key twice, depriving Rejewski of his crib. They increased the number of letter pairs swapped in the plugboard from six to ten. And they added two more scramblers, so there were 60 possible scrambler orders instead of only 6. By 1938 the Poles could no longer decipher Enigma messages, and the intelligence blackout was not lifted until Turing and the Bletchley Park cryptanalysts, again using decomposition techniques, broke the more complicated version in August 1940. (A good history of Enigma can be found here. You can try it yourself on this virtual Enigma machine.)

With the advent of computers in the 1950s and 1960s encryption techniques began to be freed of hardware limitations. The Enigma machine was bulky and complex, but an Enigma program is trivial, and increasingly complex algorithms were tried. The best of them was called Lucifer, developed by Horst Feistel for IBM. Lucifer relies, like Enigma, on a combination of transposition and substitution. (In the end, as in the beginning, are transposition and substitution.) But it’s orders of magnitude more complex. Lucifer, like most modern cryptographic algorithms, is a block cipher: it translates messages into binary digits, breaks them into blocks of 64, and encrypts them one at a time, using a series of 16 “rounds.” Simon Singh compares the process to kneading dough.

The U.S. government adopted Lucifer in 1976 as its official encryption standard, prosaically renaming it DES (Data Encryption Standard). It remained the standard algorithm until three years ago, when it was replaced by Rijndael (pronounced, approximately, Rhine-doll). DES is still theoretically unassailable. Its weakness lies not with the algorithm itself but the fact that the key, 56 bits, is too short; computers are now barely fast enough to check all the possibilities. Many experts suspect that the National Security Agency insisted on a 56-bit key because it didn’t want to endorse an algorithm it couldn’t break itself. (Update: My father, who was there, denies this story, and provides an authoritative account in the comments.)

OK, now we have an unbreakable algorithm. We can pack our bags and go home, right? Not so fast. There remains the problem of key distribution. If you and I want to encrypt our messages, we still need to share a secret, the encryption key. We can meet to agree on it, or I can send it to you by FedEx or carrier pigeon, but even with only two parties involved the logistical difficulties are considerable.

Cryptographers had always assumed that ciphers required a shared secret. Two Stanford researchers, Martin Hellman and Whitfield Diffie, asked themselves why this should be so. Diffie and Hellman wanted to know if it was possible for two strangers, with no previous agreements, to encrypt securely to each other.

Remarkably enough, they discovered, after a few years of dead ends, a way to do this simple enough to demonstrate on the back of a bar napkin. Suppose Alice and Bob — in the literature it’s always Alice and Bob — want to agree on a secret, which they will use as a key to encrypt subsequent messages. First Alice and Bob agree on two numbers, an exponent base, Y, and a modulus, P. We’ll choose small numbers, Y=5 and P=7, to keep it simple. They exchange these numbers openly. Next Alice and Bob each choose a secret number, call it X. Say Alice chooses 4 and Bob chooses 2. They keep these to themselves. Now they each calculate the following:

YX (mod P)

In other words, raise Y to the exponent X, divide the result by P, and take the remainder, which we’ll call Z. Alice’s result is 54 (mod 7) = 625 (mod 7) = 2, she sends to Bob. Bob’s result is 52 (mod 7) = 25 (mod 7) = 4, which he sends to Alice. Now Alice and Bob both take each other’s result and plug it into the following formula:

ZX (mod P)

For Bob, this is 22 (mod 7) = 4. For Alice, this is 44 (mod 7) = 256 (mod 7) = 4. Alice and Bob have ended up with the same number! This number is the encryption key. Of course in real life Alice and Bob would use extremely large numbers for P, Y, and X, and they would end up with an extremely large number for a key. But the amazing part is that it is impossible to deduce the key from the information that Alice and Bob exchange. Starting from zero, they now have a shared secret, and can encrypt to their heart’s content. For my money this is the greatest breakthrough in the history of cryptography.

There is one crucial limitation to Diffie-Hellman key exchange: it requires both parties to be present. It works for synchronous but not asynchronous communication. Unfortunately, the most common form of electronic communication, email, is asynchronous. Diffie set himself this problem. Until now all cryptographic systems had relied on a single key, and decryption was simply the reverse of encryption. Diffie wondered, again, why this must be. Suppose you had separate keys for encryption and decryption, and that it was impossible to deduce one key from the other. Then the encryption key could be public — in fact, you would want it to be widely publicized. Then if Alice wants to send Bob an encrypted message, she looks up Bob’s public key in a directory, encrypts the message, and sends it to Bob. Bob receives the message later and decrypts it, using his private key, at his leisure. Diffie had stumbled on the concept of public-key cryptography.

But only the concept: he still needed an implementation. This was finally supplied in 1977 by two MIT computer scientists, Ron Rivest and Adi Shamir, and a mathematician, Leonard Adleman. RSA is remarkably simple, only slightly more complicated than Diffie-Hellman key exchange, and although other public-key algorithms have since been discovered, RSA is still the principal one in use. Rivest, Shamir, and Adleman founded a company on its strength, RSA Security, and have grown very rich. (It was revealed, many years later, that three British cryptanalysts, James Ellis, Clifford Cocks, and Malcolm Williamson, working for the British government, had independently discovered key exchange and public-key cryptography years before Diffie, Hellman, and Rivest and company, but the government refused to release their findings. Don’t work for the government if you want to be rich and famous.)

RSA relies for its secrecy on the difficulty of factoring very large numbers. Most mathematicians believe that factorization is what they call, with their usual flair for terminology, a “hard” problem, meaning that it can’t be solved significantly faster than by trying all the possibilities. If they’re right, RSA will never be broken, and the history of cryptography is effectively at an end. The code makers have won, this time for good.


The Code Book by Simon Singh is an excellent, very readable overview of the history of encryption, including a cipher contest, consisting of 10 encrypted messages, ranging from the simple to the insanely difficult, with a prize of $15,000 to the first person to solve them all. Too late: a Swedish team already won.

The Codebreakers by David Kahn is the definitive history, ending at the mid-1960s, right before Diffie-Hellman and RSA. At 1100 pages, it requires considerable ambition. Whit Diffie, while he was dreaming up Diffie-Hellman key exchange and public-key cryptography, carried a copy around with him for years, which must have been awkward, since the book is nearly as tall as he is.

Applied Cryptography by Bruce Schneier. Comprehensive descriptions and source code for all major modern algorithms.

Aaron Haspel | Posted March 29, 2003 @ 12:46 PM | Code

12 Responses to “Cryptography: A Brief History, Part II”

  1. 1 1. Aaron's father

    A few quibbles about the DES.

    LUCIFER is an earlier algorithm that was developed into what became the DES. The development team was Walt Tuchman, Carl Meyer and Mike Matyas. When the NSA called for submission of algorithms in (I believe) 1973 they received many unsatisfactory submissions, but nothing from IBM. The same was true of a second call, but then Nicholas Katzenbach, formerly LBJs Attorney General and then IBMs General Counsel, insisted that Tuchman and company submit their latest method. The method was evaluated by Dennis Branstad of the (then called) National Bureau of Standards. It was officially published in 1977, and I believe it was adopted earlier that same year, not in 1976.

    A 64-bit key was pushing the limit that could implemented on a single chip at the time, and IBM standards required that eight bits by used as check bits. Hence the 56 bit key. Worries about key length could easily be relieved by double or triple encoding, using two or three 56-bit keys, but at the cost of a considerable slowdown.

    Branstad asked the NSA, among others, for an evaluation, and received a favorable one. The NSA did NOT insist on a 56-bit key, it did not change the algorithm (another popular myth is that the NSA buried a trap door in the algorithm) and it would not have computers that could break the DES by brute force until twenty-five years later. (Tuchman remarked that a brute force attack would require a computer that used all the energy of Niagara Falls to run it, and would have to be placed under the falls to cool it.)

    At the time, I taught Data Security and Privacy at IBMs System Research Institute, and Tuchman, Meyer and Branstad all lectured in my course. I knew them quite well, and I believe the account that I have repeated (I hope accurately) above.

  2. 2 2. Aaron Haspel

    Thanks Dad. I added a note in the piece referencing these remarks. You’re perfectly correct about triple-DES, which remains unbroken, by brute force or any other method, to this day.

  3. 3 3. Felicity McCarthy

    Well, I have and have read the Singh. I do not have, and have not read Kahn’s "The Codebreakers". Curses. I had to go buy it. Gee, thanks Aaron. Thanks for the link, for making it so very, very easy to buy…

  4. 4 4. Aaron Armitage

    I have a question about the ability to break DES by brute force: why not just use a relatively simple cipher and then use regular DES? If someone tried all possible keys, the results for all of them would look like gibberish. Even with all that brute computing force he just used on DES, there are pretty much infinite possibilities he’d have to try, from Ceasar ciphers and the rail-fence to Enigma (and any variations on it you could invent) to newly invented ciphers, and all that on each result he got from using brute force on DES.

  5. 5 5. Aaron Haspel

    Good question, Aaron. There are two answers. First, by doing this you no longer rely only on the secrecy of the key; you rely partly on the secrecy of the algorithm. This is "security by obscurity," and it violates Kerckhoff’s first principle.

    Second, although you could adhere to Kerckhoff by adding, say, a simple monoalphabetic substitution cipher to 56-bit DES, those can be broken so quickly that it wouldn’t add a great deal of security. Since modern computers can encrypt and decrypt DES instantaneously, you may as well take advantage of the available processing power by adding bits to the key via triple-DES, and that’s what cryptographers did.

  6. 6 6. Aaron Armitage

    I’m probably just going to show how little I know, but I’ll jump anyway — couldn’t someone steal the key, too? I know the key changes, but couldn’t you make small changes to the algorithm and communicate these the same way you do the changes in the key? Wouldn’t that make the exact algorithm you use part of the key, the way the Enigma key included the settings for the rotors?

  7. 7 7. Aaron Haspel

    Perhaps the best way to understand Kerckhoff’s principle is to consider a computer program to encrypt and decrypt. If you change the key, you change the input to the program; the program itself (the algorithm) remains the same. But if you change the algorithm, then you have to change the source code, and redistribute the new code. And you still have to keep the new algorithm secret. Once it leaks out, as it always does, same thing all over again. So which would you rather change, the key or the algorithm?

  8. 8 8. Aaron Armitage

    I suppose what I’m getting at is like instructions to use one program rather than another (when both are already sitting on the computer), but for that to be practical you need a predefined set of prgrams, which set would have to be freaking huge to get any benefit, which leads back to the second point in your reply to my first post — it’s easier just to add bits to the key.

  9. 9 9. David Gillies

    One of the more intriguing possibilities with DES is that the designers came up with the idea of linear cryptanalysis and optimised the S-boxes to thwart it, long before linear cryptanalysis was discussed in the open literature. Certainly when one looks at the detailed design of the S- boxes, there’s something very interesting going on there.

    It also might be a good idea to point out that naive double encryption does not increase security; triple encryption is needed to double the effective key length.

    There’s an additional wrinkle with multiple encryption, as well. It has been shown that DES is not a group i.e. \exists K_1, K_2 such that \not\exists K_3 for which E_(K_3)(P) = E_(K_2)(E_(K_1)(P))

    In other words, there is a pair of keys such that encryption by one, followed by the other, yields a ciphertext that cannot by reached by single encryption with any key from the keyspace. This is a necessary but not sufficient condition to make a cipher maximally secure under multiple encryption (needless to say a cipher that is a group is no more secure under multiple encryption than single encryption). A more rigorous condition is
    \forall K_1, K_2 \not\exists K_3. I did a bit of work (thus far unpublished) on this. We termed a cipher like this to be a 2-nongroup.

  10. 10 10. Bill Kaplan

    Where does steganography fit in all this?

  11. 11 11. Aaron Haspel

    David: Thanks for the interesting remarks on the technical details of DES, which were beyond the scope of the article. I don’t know if its inventors anticipated linear cryptanalysis, but it’s certainly possible. And you’re right that I should have pointed out that triple, not double encryption is required to double the effective key length.

    Bill: Steganography is a sideline in cryptographic history. Its technical weakness, of course, is that it relies on algorithm secrecy, and it hasn’t seen military use since the microdot, in WWI. Steganography’s great advantage is that it hides the fact that you’re encrypting at all, useful if, say, you live under a dictatorship.

  12. 12 12. Alan Bruzzi

    I was wondering where my reading level program would fit into cryptography. It takes a sentence out of a book, and computes its reading age. For example, John 3:16, spoken by Jesus Christ, would give a reading age of 33, because that’s when He died. Also, my program computes the age of the Virgin Mary, when she got married, to be 14. It’s an incredible program, but I just can’t figure out where it would be classifed under cryptography, because it converts a whole ASCII sentence into a single value, which would be the person’s age.
    Please help…


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