In Singh's The Code Book, the story of Mary Queen of Scots illustrates the dangers of having a false sense of security. There are countless examples throughout history, but perhaps the most well-known example of a false sense of security is George Washington's crossing of the Delaware to attack the British on that fabled December night in 1776. The British had wrongfully believed that Washington's men were incapacitated and unable to attack, and as such they let down their guard. As we all know, Washington and his men pounced at this opportunity and were able to turn the tide in the American Revolution. If the British had not become so complacent and careless in their actions then the very country we live in probably does not exist today.
In this same sense, Mary and her fellow conspirators "let down their guard" by explicitly detailing plans of attack, names of conspirators, and other incriminating information in their letters. In saying that "The cipher of Mary Queen of Scots clearly demonstrates that a weak encryption can be worse than no encryption at all" (Singh 41), Singh is telling us that if someone believes they are using a strong encryption system, even if it is easy to crack, then they will be apt to send important information via the encryption system. However, if one knows that an encryption system is insecure, then they will be much more likely to restrict the information in the letters. In Mary's case, she fell victim to believing that her encryption system was much stronger than it was, and as a result once Thomas Phellipes easily deciphered the letters, she was sentenced to death. If Mary's group of conspirators had known their code could be easily broken, perhaps they would have been able to successfully take back the throne.
While this would seem to suggest to others using cryptography that they should not send any incriminating information via enciphered text, at the same time there might not be a better option. One has to wonder what better alternatives Mary and her co-conspirators had, even if they had known that their code could be broken. The letters were all being intercepted anyways, so in reality the plan could never have succeeded. However, Mary did teach anyone contemplating the use of encryption at least one thing:
A False Sense of Security + Treason = Death