Evaluating computing systems and classifying them by the security properties they provide is not new [13, 14]. Other researchers [8, 9] have pointed out the difficulty of evaluating security and the apparent binary nature of security given discoveries of system vulnerability. Here, I compare the role of security evaluations with that of cryptographic security parameters, and relate the difficulty of arriving at security metrics with the Monty Hall Problem. Additionally, I argue that trying to represent the security of a system by either a single numeric value or constructing some digraph using which systems are compared is a Quixotic affair: security needs are application dependent, and no single total or partial ordering can provide all the information needed. I give example scenarios that demonstrate the need for multi-faceted security rating systems.