Cyberwarfare: A deep dive into the latest Gamaredon Espionage Campaign

Pierluigi Paganini February 17, 2020

Security experts from Yoroy-Cybaze ZLab have conducted a detailed analysis of an implant used by the Gamaredon APT group in a recent campaign.


Gamaredon Group is a Cyber Espionage persistent operation attributed to Russians FSB (Federal Security Service) in a long-term military and geo-political confrontation against the Ukrainian government and more in general against the Ukrainian military power. 

Gamaredon has been active since 2014, and during this time, the modus operandi has remained almost the same. The most used malware implant is dubbed Pteranodon or Pterodo and consists of a multistage backdoor designed to collect sensitive information or maintaining access on compromised machines. It is distributed in a spear-phishing campaign with a weaponized office document that appears to be designed to lure military personnel. 

In recent months, Ukrainian CERT (CERT-UA) reported an intensification of Gamaredon Cyberattacks against military targets. The new wave dates back to the end of November 2019 and was first analyzed by Vitali Kremez. Starting from those findings, Cybaze-Yoroi ZLab team decided to deep dive into a technical analysis of the latest Pterodo implant.

Technical Analysis

The complex infection chain begins with a weaponized Office document named “f.doc”. In the following table the initial malware information is provided.

ThreatGamaredon Pteranodon weaponized document
Brief DescriptionDoc file weaponized with Exploit

Table 1. Information about initial dropper

The decoy document is written using the ukrainian language mixed to many special chars aimed to lure the target to click on it, and, once opened, it appears as in the following figure.

Figure 1. Overview of the document

The document leverages the common exploit aka CVE-2017-0199 and tries to download a second stage from “hxxp://win-apu.]ddns.]net/apu.]dot”.

Figure 2. URL used by document to download the second stage

Thanks to this  exploit (Remote Code Execution exploit) the user interaction is not required, in fact the “enable macro” button is not shown. The downloaded document has a “.dot” extension, used by Microsoft Office to save templates for different documents with similar formats. Basic Information on the “.dot” file are provided:

ThreatGamaredon Pteranodon loader dot file
Brief DescriptionDot file enabling the infection of the Gamaredon Pteranodon

Table 2. Information about second stage

If we decide to open the document, we see that the document is empty, but it requires the enabling of the macro.

Figure 3. Overview of the second stage document

The body of the macro can be logically divided into two distinct parts: 

  • The first one is the setting of the registry key “HKEY_CURRENT_USER\Software\Microsoft\Office\” & Application.Version & _”\Word\Security\” and the declaration of some other variables, such as the dropurl “get-icons.]”;
  • The second one is the setting of the persistence mechanism through the writing of the vbs code in the Startup folder with name “templates.vbs”. This vbs is properly the macro executed by the macro engine of word
Figure 4. Code of the “template.vbs” stored in the Startup folder

The evidence of the written file in the Startup folder:

Figure 5. Evidence of the “template.vbs” file in the Startup folder

Analyzing the content of “templates.vbs” it is possible to notice that it define a variable containing a URL like “hxxp://get-icons.]ddns.]net/ADMIN-PC_E42CAF54//autoindex.]php” obtained from “hxp://get-icons.]ddns.]net/” & NlnQCJG & “_” & uRDEJCn & “//autoindex.]php”, where “NlnQCJG” is the name that identifies the computer on the network and “uRDEJCn” is the serial number of drive in hexadecimal encoding. From this URL it tries to download another stage then storing it into “C:\Users\admin\AppData\Roaming\” path with random name. At the end, “templates.vbs” script will force the machine to reboot. 

Figure 6. Function used to force machine reboot

The dropped sample is an SFX archive, like the tradition of Gamaredon implants.

ThreatGamaredon Pteranodon implant SFX archive
Brief DescriptionSFX Archive First Stage 

Table 3. Information about first SFX archive

By simply opening the SFX archive, it is possible to notice two different files that are shown below and named respectively “8957.cmd” and “28847”. 

Figure 7. Content of the Gamaredon Pteranodon  SFX archive

When executed, the SFX archive will be extracted and the “8957.cmd” will be run. The batch script looks like the following screen:

Figure 8. Bat script source code (with junk instructions)

It contains several junk instructions with the attemption to make the analysis harder. Cleaning the script we obtain:

Figure 9. Batch script source code (cleaned)

At this point, the batch script renames the “28847” file in “28847.exe”, opens it using “pfljk,fkbcerbgblfhs” as password and the file contained inside the “28847.exe” file will be renamed in “WuaucltIC.exe”. Finally, it will be run using “-post.php” as argument.

The fact that the “28847.exe” file can be opened makes us understand that  the “28847” file is another SFX file. Some static information about SFX are:

ThreatGamaredon Pteranodon implant SFX archive
Brief DescriptionSFX Archive Second Stage

Table 4. Information about the second SFX archive

Exploring it, it is possible to see several files inside of it,  as well as the 6323 file. The following figure shows a complete list.

Figure 10. Content of the second SFX archive

In this case, the SFX archive contains 8 files: five of them are legit DLLs used by the “6323” executable to interoperate with the OLE format defined and used by Microsoft Office. The “ExcelMyMacros.txt” and “wordMacros.txt” files contain further macro script, described next. So, static analysis on the “6323” file shown as its nature: it is written using Microsoft Visual Studio .NET, therefore easily to reverse. Before reversing the executable, it is possible to clean it allowing the size reduction and the junk instruction reduction inside the code. The below image shows the information about the sample before and after the cleaning. 

Figure 11. Static information about .NET sample before and after the cleaning

The source code looks as follows. 

Figure 12. Part of .NET sample source code

The first check performed is on the arguments: if the arguments length is equal to zero, the malware terminates the execution. After that, the malware checks if the existence of the files “ExcelMyMacros.txt” and “wordMacros.txt” in the same path where it is executed: if true then it reads their contents otherwise it will exit. 

Figure 13. Function used by .NET sample to check the presence of the “WordMacros.txt” and the “ExcelMyMacros.txt” files”

Part of the content of the variable “xVGlMEP”:

Figure 14.Piece of the “WordMacros.txt” code

There is a thin difference between the two files. 

Figure 15. Difference between “WordMacros.txt” and  “ExcelMyMacros.txt” files”

As visible in the previous figure, the only difference between the files are in the variable, registry key and path used by Word rather than by Excel. Finally the macros are executed using the Office engine like in the following figure. 

Figure 16. Winword with malicious macro

So let’s start to dissect the macros. For a better comprehension we will be considering only one macro and in the specific case we will analyze “wordMacros.txt”  ones. First of all the macro will set the registry key “HKEY_CURRENT_USER\Software\Microsoft\Office\” & Application.Version & _”\Word\Security\” and then will set up two scheduled tasks that will start respectively every 12 and 15 minutes: the first one will run a “IndexOffice.vbs” in the path “%APPDATA%\Microsoft\Office\” and the second one will run “IndexOffice.exe” in the same path. 

Figure 17. Registry keys and Scheduled tasks set by malware

Finally, the malware will write the “IndexOffice.txt” file in the  “%APPDATA%\Microsoft\Office\” path. The following figure shows what has been previously described:

Figure 18. Part of “IndexOffice.txt” file

The script will check the presence of the  “IndexOffice.exe” artifact: if true then it will delete it and it will download a new file/script from “hxxp://masseffect.]space/<PC_Name>_<Hex_Drive_SN>/post.]php”. 

Figure 19. Domain “masseffect.]space” declaration and use of the Encode function

The malware tries to save the C2 response and encoding it using Encode function. This function accepts three parameters: the input file, the output file and the arrKey; arrKey is calculated thanks to  GetKey function that accepts as input the Hexadecimal value of the Driver SN installed on the machine and returns the key as results. Part of Encode function and complete code of GetKey function are shown below.

Figure 20. Encode function 
Figure 21. Function GetKey

Visiting the web page relative to C2, it shows a “Forbidden message” so this means that the domain is still active but refuses incoming requests.

Figure 22. Browser view of the URL “masseffect.]space” 


Gamaredon cyberwarfare operations against Ukraine are still active. This technical analysis reveals that the modus operandi of the Group has remained almost identical over the years. 

The massive use of weaponized Office documents, Office template injection, sfx archives, wmi and some VBA macro stages that dynamically changes,  make the Pterodon attack chain very malleable and adaptive. However, the introduction of a .Net component is a novelty compared to previous Pterodon samples.

Further technical details, including Indicators of Compromise and Yare rules, are reported in the analysis published by the experts at the Cybaz-Yoroi ZLAB
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Pierluigi Paganini

(SecurityAffairs – hacking, Gamaredon)

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