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4

This sounds like a classic codebook or nomenclator. Even if we assume a perfect random oracle that generates a completely random codeword for each word of English text, I agree with otus that frequency attacks and N-grams would likely be able to decode the most-frequently-used words. Also, a known-plaintext attack (or worse, a chosen-plaintext attack) would ...


5

The feasibility depends a lot on the length of the corpus. The more statistics, the better guesses an attacker would be able to make. He'll try to use statistical attacks to fit the frequency curve of the tokens to the frequency curve of English words. This will allow him to guess the preimages of more frequent words with high confidence, but will he be ...


2

Provided the text was long enough and used an simple codebook substitution cipher, absolutely. English has common bigrams and trigrams as well as words that are typically positioned in certain places in sentences, like The. Also, if punctuation was tokenized in the codebook, it would be incredibly easy to guess or identify . and ,, because those will be ...



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