Abstract  Differential cryptanalysis was introduced as an approach to analyze the security of DES-like cryptosystems. The first example of a DES-like cryptosystem was Lucifer, the direct predecessor of DES, which is still believed by many people to be much more secure than DES, since it has 128 key bits, and since no attacks against (the full variant of) Lucifer were ever reported in the cryptographic literature. In this paper we introduce a new extension of differential cryptanalysis, devised to extend the class of vulnerable cryptosystems. This new extension suggests key-dependent characteristics, calledconditional characteristics, selected to increase the characteristics' probabilities for keys in subsets of the key space. The application of conditional characteristics to Lucifer shows that more than half of the keys of Lucifer are insecure, and the attack requires about 2³⁶ complexity and chosen plaintexts to find these keys. The same extension can also be used to attack a new variant of DES, called RDES, which was designed to be immune against differential cryptanalysis. These new attacks flash new light on the design of DES, and show that the transition of Lucifer to DES strengthened the later cryptosystem.