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Ransomware has been a growing threat to end-users in the past few years. In response, there is also a burgeoning market for anti-ransomware defense products, as well as research prototypes that explore more advanced, behavioral analyses. Intuitively, ransomware should be amenable to identification through behavioral analysis, since ransomware recursively walks a user’s files and encrypts them, overwriting or deleting the plaintext. This paper contributes a study of the effectiveness of these behavior-based ransomware defenses, from both commercial products and academic proposals. We drive the study with a dead simple ransomware, augmented with a number of both straightforward and new evasion techniques. Surprisingly, our results indicate that most commercial products are strikingly ineffective. Ten out of 15 commercial products could not detect our simple ransomware without any evasive techniques; most of the rest were evaded and able to ransom user data with some combination of simple techniques. Only one tool appears to correctly identify our ransomware, but suffers from staggering false positives, including flagging Windows Explorer, Firefox, and Notepad as ransomware during routine operation. Our paper identifies a number of techniques to manipulate entropy to match the original file. The paper further shows that partial encryption, of as little as 3–5% of a file’s data is sufficient to ransom most file formats. Finally, we show that a combination of these techniques can render an aggregate malice score that is well below that of a Linux kernel compile. In summary, these results indicate that it is highly likely that ransomware will be able to adapt its behavior to fit within the range of expected benign behaviors, avoiding detection even by future generations of behavioral ransomware detectors.