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When compared to signature-based Intrusion Detection Systems (IDS), anomaly detectors present the potential advantage of detecting previously unseen attacks, which makes them an attractive solution against zero-day exploits and other attacks for which a signature is unavailable. Most anomaly detectors rely on machine learning algorithms to derive a model of normality that is later used to detect suspicious events. Such algorithms, however, are generally susceptible to evasion by means of carefully constructed attacks that are not recognized as anomalous. Different strategies to thwart evasion have been proposed over the last years, including the use of randomization to make somewhat uncertain how each packet will be processed. In this paper we analyze the strength of the randomization strategy suggested for Anagram, a well-known anomaly detector based on n-gram models. We show that an adversary who can interact with the system for a short period of time with inputs of his choosing will be able to recover the secret mask used to process packets. We describe and discuss an efficient algorithm to do this and report our experiences with a prototype implementation. Furthermore, we show that the specific form of randomization suggested for Anagram is a double-edged sword, as knowledge of the mask makes evasion easier than in the non-randomized case. We finally discuss a simple countermeasure to prevent our attacks.