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The Data Encryption Standard (DES) defines an indexed set of permutations acting on the message space ℳ ={0,1}. If this set of permutations were closed under functional composition, then the two most popular proposals for strengthening DES through multiple encryption would be equivalent to single encryption. Moreover, DES would be vulnerable to a known-plaintext attack that runs in 2 steps on the average. It is unknown in the open literature whether or not DES has this weakness.Two statistical tests are presented for determining if an indexed set of permutations acting on a finite message space forms a group under functional composition. The first test is a “meet-in-the-middle” algorithm which uses  time and space, where  is the size of the key space. The second test, a novel cycling algorithm, uses the same amount of time but only a small constant amount of space. Each test yields a known-plaintext attack against any finite, deterministic cryptosystem that generates a small group.The cycling closure test takes a pseudorandom walk in the message space until a cycle is detected. For each step of the pseudorandom walk, the previous ciphertext is encrypted under a key chosen by a pseudorandom function of the previous ciphertext. Results of the test are asymmetrical: long cycles are overwhelming evidence that the set of permutations is not a group; short cycles are strong evidence that the set of permutations has a structure different from that expected from a set of randomly chosen permutations.Using a combination of software and special-purpose hardware, the cycling closure test was applied to DES. Experiments show, with overwhelming confidence, that DES is not a group. Additional tests confirm that DES is free of certain other gross algebraic weaknesses. But one experiment discovered fixed points of the so-called “weak-key” transformations, thereby revealing a previously unpublished additional weakness of the weak keys.

Is the Data Encryption Standard a group? (Results of cycling experiments on DES)