The strength of the Vigenère Cipher depends largely on the length of the keyword. If the keyword is just one letter, then it is nothing more than a simple shift cipher; if the keyword is the same length as the plain text, there will be little to no discernable pattern. However, Singh clearly demonstrates that even with a keyword as long as the text, breaking the Vigenère is doable by guessing common words like “the.”
Even though it is relatively straightforward to break even these more secure ciphers, doing so in practice is often much harder. Primarily, this is because of the amount of guessing and checking required and the creative insights necessary to realize the best way to break the code. During the process of deciphering the message, and essential step is guessing words either in the plain text or in the keyword, and if your guess is wrong, you have to backtrack until you are confident that all of your work is correct and start from there again. This makes the process of cryptanalysis tedious and time-consuming.
Once you know what method to use to break the cipher, deciphering the message is only a matter of time, but often, figuring out how to approach a complicated cipher takes even the smartest cryptanalysts years to figure out on their own. For example, breaking the simple Vigenère cipher was not difficult; once Charles Babbage figured out how to break it, the Vigenère went from being an unbreakable cipher to extremely insecure overnight. This demonstrates that breaking the cipher itself is often not the most difficult part; the hardest part of breaking complex ciphers is coming up with a foolproof method which exploits weaknesses in the cipher.