Choosing the most effective word-mangling rules to use when performing a dictionary-based password cracking attack can be a difficult task. In this paper we discuss a new method that generates password structures in highest probability order. We first automatically create a probabilistic context-free grammar based upon a training set of previously disclosed passwords. This grammar then allows us to generate word-mangling rules, and from them, password guesses to be used in password cracking. We will also show that this approach seems to provide a more effective way to crack passwords as compared to traditional methods by testing our tools and techniques on real password sets. In one series of experiments, training on a set of disclosed passwords, our approach was able to crack 28% to 129% more passwords than John the Ripper, a publicly available standard password cracking program.

In this paper we attempt to determine the effectiveness of using entropy, as defined in NIST SP800-63, as a measurement of the security provided by various password creation policies. This is accomplished by modeling the success rate of current password cracking techniques against real user passwords. These data sets were collected from several different websites, the largest one containing over 32 million passwords. This focus on actual attack methodologies and real user passwords quite possibly makes this one of the largest studies on password security to date. In addition we examine what these results mean for standard password creation policies, such as minimum password length, and character set requirements.

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