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This can be broken. The exact nature of the attack will depend what modulus you use for the Hill cipher: are you working modulo a prime number, or working modulo 26? Working modulo a prime $p$ A simple attack, with no fancy mathematics needed. One simple attack is to start by requesting the encryption of the 26 messages AAAA, BBBB, CCCC, DDDD, ..., ZZZZ. ...



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