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For instance say you encrypt text using the one time pad and you end up with some scrambled text that appears illegible.

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OK, so somebody suspects that your data has been encrypted.

(Or maybe they just know that it is; it's generally safest to assume that they do.) How would they go about breaking the encryption?

We don't really know what your dates might be about, so let's just make a random guess and say that they're people's birthdays. A suspicious person could examine your birthday data and see if it matches these expected patterns.

If it does not, they might suspect that it has been encrypted, or otherwise tampered with.

This is also easily detectable, although recovering the key may be more — possibly much more — difficult.) In fact, the methods to use for breaking your cipher are basically the same as one would use to break a simple Caesar cipher.

Both are simple additive monoalphabetic substitution ciphers; the only difference is that, in your case, the "alphabet" consists of months rather than of letters.

For this simple cipher, this will also immediately reveal the key.

(A more complex format-preserving cipher would typically yield a frequency distribution that looks a lot closer to uniform than normal data would.

Say you wanted to preserve the linkage to people and their birthdates.

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