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Comparison of Entropy Calculation Methods for Ransomware Encrypted File Identification

Davies, Simon R.; Macfarlane, Richard; Buchanan, William J.



Ransomware is a malicious class of software that utilises encryption to implement an attack on system availability. The target’s data remains encrypted and is held captive by the attacker until a ransom demand is met. A common approach used by many crypto-ransomware detection techniques is to monitor file system activity and attempt to identify encrypted files being written to disk, often using a file’s entropy as an indicator of encryption. However, often in the description of these techniques, little or no discussion is made as to why a particular entropy calculation technique is selected or any justification given as to why one technique is selected over the alternatives. The Shannon method of entropy calculation is the most commonly-used technique when it comes to file encryption identification in crypto-ransomware detection techniques. Overall, correctly encrypted data should be indistinguishable from random data, so apart from the standard mathematical entropy calculations such as Chi-Square (χ2), Shannon Entropy and Serial Correlation, the test suites used to validate the output from pseudo-random number generators would also be suited to perform this analysis. The hypothesis being that there is a fundamental difference between different entropy methods and that the best methods may be used to better detect ransomware encrypted files. The paper compares the accuracy of 53 distinct tests in being able to differentiate between encrypted data and other file types. The testing is broken down into two phases, the first phase is used to identify potential candidate tests, and a second phase where these candidates are thoroughly evaluated. To ensure that the tests were sufficiently robust, the NapierOne dataset is used. This dataset contains thousands of examples of the most commonly used file types, as well as examples of files that have been encrypted by crypto-ransomware. During the second phase of testing, 11 candidate entropy calculation techniques were tested against more than 270,000 individual files—resulting in nearly three million separate calculations. The overall accuracy of each of the individual test’s ability to differentiate between files encrypted using crypto-ransomware and other file types is then evaluated and each test is compared using this metric in an attempt to identify the entropy method most suited for encrypted file identification. An investigation was also undertaken to determine if a hybrid approach, where the results of multiple tests are combined, to discover if an improvement in accuracy could be achieved.

Journal Article Type Article
Acceptance Date Oct 20, 2022
Online Publication Date Oct 21, 2022
Publication Date Oct 21, 2022
Deposit Date Oct 21, 2022
Publicly Available Date Oct 24, 2022
Publisher MDPI
Peer Reviewed Peer Reviewed
Volume 24
Issue 10
Article Number 1503
Keywords entropy; randomness; crypto-ransomware; mixed file dataset; PRNG
Public URL


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