I am working on a anti-ransomware project. It simply monitors the filesystem, and watches for files being created, and deleted. (also monitors for known ransomware file extensions.)

Basic Operation: If (File X in Directory Y is created), and soon-after (File Z in Directory Y is deleted.) Scan File X and try to determine if it is an encrypted file.

I am stuck because I have no idea how to determine if a file is encrypted or not. I have read through quite a few threads on SO, but I've still turned up empty.

My question is basically: What methods can be used to determine if a file is encrypted?

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    Legitimate files will have some sort of magic number in their header, and some structure overall. You can also look at the entropy of a file. An encrypted file should have an even distribution of all 255 possible bytes. Here's a link about determining encryption vs. compression. – RoraΖ May 6 '16 at 16:13
  • I found this in another thread on SO. "you can infer that its probably been encrypted with AES or some other 128bit block cipher by testing if the length of the data in bytes is a multiple of 16, suggesting a 128bit block cipher with padding on the last block" Is this method also a legitimate way to check for encryption? – Nobody May 6 '16 at 16:29
  • @RoraZ, throw that into an answer so I can upvote it! – Mike Ounsworth May 6 '16 at 16:30
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    Note that ransomware does not always encrypt the whole file, sometimes it just encrypts stuff after the file header, so the magic number will be intact, and the length of the file will not be a multiple of the block size. You really need to look at some samples of encrypted files from the ransomwares you're trying to protect against. – Mike Ounsworth May 6 '16 at 16:34
  • I have written out a java application, that utilizes Monte Carlo Pi, and Chi-square distribution to detect if a file is encrypted or not. They are pseudorandom tests that separates between encrypted files and compressed files as well. Encryption Detector – Kiat Han Mar 3 '17 at 20:19

You can use the file command if available in your environment (a standard part of BSD/OSX/Linux). For example, once encrypted content is available:

$ gpg --encrypt test-encrypted -r sample@sample.com

Enter the user ID.  End with an empty line: 
$ ls                       
test-encrypted      test-encrypted.gpg
$ mv test-encrypted.gpg testfile.txt

file can identify it as GPG Encrypted content:

$ file testfile.txt 
testfile.txt: GPG encrypted data

However, this only shows information based on the headers and trailers. A while back, someone wrote a Powershell script to find Cryptolocker files (link to PS script) which may or may not help you. The issue you will run into is: "HOW was this encrypted?" For example, if an attacker just creates a complex password for a "password protected zip" file, that isn't encryption per-se, so your script will be detected as a zip file, not an encrypted file.

Also noteworthy is, many of these ransomware files change on every iteration. E.g., locky appends a *.locky to each file, so while some may be easy to detect, imagine if all your files were renamed to random checksums. Now you cannot identify files: E.g.:

MD5 ("salesfile") = 64d11ab29c2d78b325d8a944119d1150.doc
MD5 ("payrollfile") = d9087b158cd38e844999456d17611f1c.doc
MD5 ("engineeringfile") = 14e8e9011a4d3343df39e35fc7f2cd29.doc
MD5 ("researchfile") = 26779202429523339305a90e6ec74146.doc
MD5 ("managementfile") = 419765bc586cdd1bf741afe771951bec.doc

Now you have a bigger issue. Which file is more mission critical to spend time "cracking/decrypting/etc." For the most part, the file command on Unix based systems, and or the Powershell script should give you a starting point. There is also YARA if you REALLY want to be technical about it. Create a YARA signature, and use that to search.

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    This is exactly why I can't wait for Bash on windows 10. It will be a godsend. Also thanks much, there is quite alot of useful information in your post, and in these links. – Nobody May 6 '16 at 16:41
  • @Nobody Note that file works as shown because PGP encrypted files will have a "marker" that it detect. Files created by ransom wear could may well not have this marker. – TripeHound Feb 1 at 8:41

You could run ent to see how much entropy a file has, a file with high entropy is likely either compressed or encrypted (or both). A problem is that JPEG, XLSX and ZIP are compressed, so actually compressed files are very common.

If you suspect that X is an encrypted version of file Z then you could check if they have similar sizes, plus small delta for encryption headers.


If you have a clean system, you can use PowerShell to generate hashes for the valid files (i.e., you may have valid encrypted, compressed, binary and regular files); and each sweep you generate new hashes and compare if any hash has changed.

Based on type, etc you can determine if this is normal behavior.

For instance, I look use PowerShell Get-Process in Windows to alert if there are changes to processes, etc.

Here is demonstration of idea that can be expanded on.

PS C:\windows\system32> ## Demonstration
#  Show how you can fingerprint a server and find out if any new 
#  processes are started since boot or last baseline
Get-Process * | Export-Clixml 'D:\Digital Forensics\__\baseline-local-GPROC-000.xml'
$gpbaseline000 = Import-Clixml 'D:\Digital Forensics\__\baseline-local-GPROC-000.xml'

Start-Process notepad.exe

Get-Process * | Export-Clixml 'D:\Digital Forensics\__\baseline-local-GPROC-001.xml'
$gpbaseline001 = Import-Clixml 'D:\Digital Forensics\__\baseline-local-GPROC-001.xml'

Compare-Object $gpbaseline000 $gpbaseline001 -Property processname

Sample PowerShell session within PowerShell ISE See image for sample output.

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