New answers tagged chosen-ciphertext-attack
I unfortunately don't have enough reputation to comment, forgive the answer that is a link to another answer. Your question is explained well in this answer: http://crypto.stackexchange.com/a/12706/17884
There are several algorithms available which can attack a playfair cipher. Hill climbing might be one option. Basically it starts with a random key (assuming it's the best one) and decrypts the cipher. The resulting clear text is scored using a fitness function. Then small changes are applied to the key and if the resulting clear text of the modified key ...
It's not elegant, but the brute force method is to write a program that creates a table of 25x25 digraphs (assuming i=j), yielding 625 rows. I'd also add a column that lists the relative frequency of each digraph (given enough ciphertext you can use that to identify frequent substitutions, as you already have done). You start off with 625! possible ...
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