Early attempts to thwart frequency analysis attacks on ciphers involved using *homophonic substitutions*, ie. some letters map to more than one ciphertext symbol. The earliest known example of this, from 1401, is shown below: [![Homophonic substitution][1]][1] [[Source]][2] One variant is the *nomenclator*, where codewords are used to substitute many common words and names. The example below was used by Mary Queen of Scots in 1586. [![Mary Queen of Scots Cipher][3]][3] [[Source]][4] According to Wikipedia, > By the late eighteenth century, when the system was beginning to die > out, some nomenclators had 50,000 symbols. What is the best way to go about cracking those kinds of ciphers as the number of symbols used increases? [1]: https://i.sstatic.net/OXUek.png [2]: http://www.quadibloc.com/crypto/pp010301.htmhttp://www.quadibloc.com/crypto/pp010301.htm [3]: https://i.sstatic.net/oEHCp.gif [4]: http://www.simonsingh.net/The_Black_Chamber/maryqueenofscots.html