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I saw a statement that the probability of finding a key $k'$ to simulate 3 keys $k_1$, $k_2$, $k_3$ is neglectable: $\mathrm{Enc}(k_3,\mathrm{Enc}(k_2,\mathrm{Enc}(k_1,x))) = \mathrm{Enc}(k′,x)$

When not considering MITM attack, the probability of brute forcing triple DES is $1/2^{168}$. According to the statement, does that mean the probability of finding $k'$ is also $1/2^{168}$ so it is negligible? Do I understand it correctly?

pXN
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No. In the triple encryption case, we expect that the chance of such a key existing at all is about $2^{56}/64!\approx 2^{-240}$ (assuming a 64-bit block size and 56-bit single key space). There's no particular structure that should make is treat the $2^{168}$ permutations corresponding to the different possible possible choices of 3 keys as anything other than a random permutation, likewise for the $2^{56}$ permutations corresponding to a single encryption.

(ETA: Poncho points out that there is some structure for four known DES keys for which encryption and decryption are the same. In the case, where $k_2$ is such a key and either $k_1$ or $k_2$ is also, then the triple encryption is equivalent to a single key encryption. This happens with probability roughly $2^{-109}$. There are also six pairs of semi-weak keys where encryption without one is the same as decryption with another, again if $k_2$ belongs to one of these pairs and either $k_1$ or $k_2$ then there is single key equivlance. This has additional probability roughly $2^{-107.4}$)

However, triple DES is not threefold encryption but rather DES-encryption with one key $k_1$, DES-decryption with another key $k_2$ and DES-encryption with a third key $k_3$. In the case $k_1=k_2$ this structure is equivalent to single DES-encryption with $k_3$ and in the case $k_2=k_3$ it is equivalent to single DES-encryption with $k_1$. If $k_1,k_2,k_3$ are chosen independently, uniformly at random the chance of one of these two occurrences is about $2^{-55}$, and as before we expect other triples to correspond to single keys with probability $2^{56}/64!$.

If there is an equivalent single key, we expect to be able to find it with $2^{56}$ work and one or two matched plain and cipher pairs. We do this just be exhausting the single key space. The chance of a false positive on one matched pair is about $2^{-8}$ and on two matched pairs is about $2^{-72}$.

Daniel S
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