What did DeathStalker hide between two ferns?

DeathStalker is a threat actor who has been active starting 2012 at least, and we exposed most of his past activities in a previous article, as well as during a GREAT Ideas conference in August 2020. The actor draught our attention in 2018, because of distinctive attacks characteristics that did not fit the usual cybercrime or state-sponsored activities, making us believe that DeathStalker is a “hack-for-hire” company.

DeathStalker leveraged several malware strains and delivery chains across years, from the Python and VisualBasic-based Janicab, to the PowerShell-based Powersing, passing by the JavaScript-based Evilnum. The actor consistently used what we call “dead-drop resolvers” (DDRs), which are some obfuscated content hosted on major public Web services like YouTube, Twitter or Reddit; and which once decoded by a malware would reveal a command-and-control (C2) server address. DeathStalker also consistently leveraged anti-detection and antivirus evasion techniques, as well as intricated delivery chains, that would drop lots of files on target’s filesystems. To kick-start an infection, DeathStalker usually relies on spear-phishing emails with attachments, or links to public file-sharing services, as well as Windows shortcuts-based script execution. We have identified DeathStalker’s malware compromises within clusters or varied targets in all parts of the world, with a possible focus on law and consultancy offices, as well as FINTECH companies, but without any clear or stable visible interest. The targeting does not seem to be politically or strategically defined and does not fit in usual financially motived crime. As so, we concluded that DeathStalker is a cyber-mercenaries organization.

While tracking DeathStalker’s Powersing-based activities in May 2020, we detected a previously unknown implant that leveraged DNS over HTTPS as a C2 channel, as well as parts of its delivery chain. We named this new malware “PowerPepper”. We first spotted a variant of PowerPepper in the wild in mid-July 2020, as dropped from a Word Document that had been submitted on a public multiscanner service. PowerPepper implant and associated delivery chain has been continuously developed and operated since.

Meet PowerPepper: the spicy implant that your bland scripts setup needed

PowerPepper implant

PowerPepper is a Windows in-memory PowerShell backdoor that can execute remotely sent shell commands. In strict accordance with DeathStalker’s traditions, the implant will try to evade detection with various tricks like mouse movements detection, client’s MAC addresses filtering, Excel application handling and antivirus products inventory.

The implant’s C2 logic stands out, as it is based on communications via DNS over HTTPS (DoH), using CloudFlare responders. PowerPepper first try to leverage Microsoft’s Excel as a Web client to send DoH requests to a C2 server, but will fall back to PowerShell’s standard Web client, and ultimately to regular DNS communications, if messages cannot go through.

C2 communications content between the implant and servers is encrypted. We noticed that PowerPepper and the previously described Powersing use an almost identical PowerShell implementation of AES encryption, with only the AES padding mode and a function input format being changed.

PowerPepper DNS command and control

PowerPepper regularly polls a C2 server for commands to execute. In order to do so, the implant sends TXT-type DNS requests (with DoH or plain DNS requests if the later fails) to the name servers (NS) that are associated with a malicious C2 domain name. If the target which runs the implant is validated (we cover that later), the server replies with a DNS response, embedding an encrypted command. Both requests and responses contain patterns that can be easily detected with network intrusion detection systems, but that has been changed across implants variants.

The commands execution results are sent back to the server through a batch of variable-length A-type DNS requests, where queried hostnames contain an identifier, data length, and encrypted data.

# Command result feedback initialization DNS request hostname: 
# Command result feedback data slices DNS requests hostnames: <identifier>.ef.<domain> <identifier>.ef.<domain> <identifier>.ef.<domain> 
# Command result feedback termination DNS request hostname: 

During the course of our investigations, we noticed that the PowerPepper C2 name servers were actually open DNS resolvers, that always resolved arbitrary hostnames with the same IP addresses: (a US Navy owned server), and (HSBK UK owned servers). Using this fact and reverse DNS resolutions historical data, we have been able to preemptively identify PowerPepper C2 domains.

PowerPepper signaling and targets validation

On top of the DNS C2 communication logic, PowerPepper is also signaling successful implant startup and execution flow errors to a Python backend, through HTTPS. Such signaling enables targets validation and implant execution logging, while preventing researchers to further interact with PowerPepper malicious C2 name servers. It has also been used directly from some of the malicious documents that were involved in PowerPepper delivery, thought the remote-sources links feature in Office documents.

The signaling Python backends were hosted on a public and legitimate content hosting Web service which is named “PythonAnywhere“, and which allows users to build websites. Discovered Python backend endpoints were shut down by PythonAnywhere in coordination with us. As a result, DeathStalker tried to adapt the signaling feature by removing it from most PowerPepper delivery documents (but keeping it in the implant itself), and by adding a legitimate but compromised WordPress website as a reverse-proxy between implants and backends.

PowerPepper delivery chains: a surprising journey into mercenaries’ tricks, from Russian dolls to plant-covered steganography

The macro-based delivery chain: when you are way too much into this whole “Russian dolls” idea

The first type of PowerPepper delivery (or infection) chain we encountered, back in July 2020, is based on a malicious Word document. Although we could not confirm how such document had been distributed to targets, infection trails and documents we analyzed would show that such item is either embedded as a spear-phishing mail body, or downloaded from a malicious link in a spear-phishing email. This infection chain varied slightly between July and November 2020: some dropped file names, integrated code or remote links changed, but the logic stayed the same.

We will not dive deep in the details of the delivery workflow, as main tricks are approached later. It should however be noted that the delivery chain is based on a monolithic document that embeds all required malicious items. This document notably contains a decoy content, and the malicious logic is handled by Visual Basic for Application (VBA) macros, which ultimately run PowerPepper and setup its persistence.

The LNK-based delivery chain: your direct shortcut to spiciness

This infection chain is based on a Windows shortcut file, with a misleading “.docx.lnk” double extension, and constitutes a more modular approach to PowerPepper delivery.

The delivery chain is very similar to the macro-based one, but implements two major changes:

  • the malicious macros logic is moved to malicious PowerShell scripts, and the first one is directly embedded in the shortcut file, so there are no more VBA macros;
  • the Word document from this chain is just a decoy and malicious files storage pack, and is downloaded from a remote location (a public file sharing service) instead of directly embedded somewhere.

The malicious LNK files were most likely distributed as ZIP-ed attachments within spear-phishing mails, and files that are dropped from this delivery chain of course change across varians as well.

A quick look at the decoy contents

Some malicious documents that we could retrieve contained a social-engineering banner, asking users to enable macros execution, and thus explaining how the malicious logic from the macro-based delivery chain could actually be triggered, while macros are disabled by default on most modern Office settings.

Decoy contents we could retrieve are varied: the first we found in the wild was about carbon emissions regulations, but we also identified a fake travel booking form for a very specific event which is planned next year in Turkey, and of course some are about the coronavirus.

We could link most of the decoy contents back to original contents that are published on the Internet by their initial authors, which means that DeathStalker did not craft such contents, but picked appropriate ones that are available on the Internet as is. One of the decoy contents contained sender details that impersonated a legitimate travel agent identity but included changed contact details.

A PowerPepper tricks compilation

PowerPepper delivery chains leverage a lot of obfuscation, execution and masquerading tricks to hinder detection, or deceive targets that are possibly keen on knowing what is happening on their computers, so we thought we should describe some.

Trick #1: hide things in Word embedded shapes properties (and make macro comments fun again)

DeathStalker hides strings in Word embedded shapes and objects (OLE packages) properties, like the “hyperlink” property, to obfuscate the malicious execution workflow, as well as reconstruct and execute commands or scripts.

bell = "JohnSnow123"
Documents.Open FileName:=best & FName, PasswordDocument:=CStr(bell), Visible:=False
With Application:
            .Run "boat", belt
' this function is totally legit and if you are an av you should totally let us pass
Function boat(both)
' checks if the type is 7
If .Type = 7 Then
If .OLEFormat.Application = "Microsoft Word" And .OLEFormat.ClassType = "Package" Then
            band = Split(.Hyperlink.Address, "ps://")
            ball = ball & band(1)

These properties are notably leveraged as a second stage PowerShell script in the LNK-based delivery chain: the first stage PowerShell script which is embedded in a malicious LNK file will parse a downloaded Word document contents to extract and run a second PowerShell script. These properties artifacts can also contain parts of URLs, dropped files paths, or commands that are directly leveraged by macros in the macro-based delivery chain.

We can also notice from the code extract above that DeathStalker uses macros to further open another subdocument, which is embedded in the first malicious document from the macro-based delivery chain. Last but not least, comments are very helpful.

Trick #2: use Windows Compiled HTML Help (CHM) files as archives for malicious files

In the course of their PowerPepper delivery workflows, DeathStalker leverages CHM files as containers to better evade detection, and uses a Windows built-in tool called “hh” to unpack content, from VBA macros or LNK-embedded PowerShell script.

All the files that are dropped on targeted computers fro delivery chains and that are necessary to run PowerPepper are contained in such archives. The CHM files are embedded in the malicious Word (sub)document of the delivery chains.

Trick #3: masquerade and obfuscate persistent files

DeathStalker uses a Visual Basic Script (VBS) loader to start PowerPepper execution. The loader is launched immediately after delivery, and at each computer startup then, thanks to a companion launcher shortcut which is placed in a Windows startup folder.

' Copyright (c) GlobalSign Corporation. All rights reserved.
' Abstract:
' licenseverification.vbs - Verify the GlobalSign software
' Usage:
' licenseverify [-software]
const L_Help_Help_General05_Text   = "-a     - add a port"
const L_Help_Help_General06_Text   = "-d     - delete the specified port"
const L_Help_Help_General34_Text   = "417079070765161B1C0eeeeeef610520C0F69331…
CreateObject(DelPort(L_Text_Msg_Port01_Text)).Run …+DelPort(L_Help_Help_General34_Text & "7260D3…

This VBS loader is masqueraded as a GlobalSign verification tool with comments as well as deceptive variables or help strings. Furthermore, the script malicious content is obfuscated thanks to a custom encryption function.

Trick #4: hide your implant between two ferns…

And here come our plants… The previously described VBS loader will basically do one thing: deobfuscate and run a PowerShell script against a picture file, that had been previously dropped from the delivery chain.

But the picture is actually a steganography image (representing… ferns), that will be decoded by the VBS loader-embedded script, and contains the PowerPepper implant. In the first discovered delivery chains, the steganography image actually represented peppers, hence the “PowerPepper” name.

Trick #5: get lost in Windows shell commands translation

The Windows shortcut (LNK) file from the LNK-based delivery chain is actually starting a Windows shell with an obfuscated command argument. This command is a specific form of a “FOR” Windows shell loop, that will generate the “PowerShell” string from an “assoc” shell built-in result.

The malicious LNK file will fire a PowerShell script as a result, which in turn will recompose a second stage script from a downloaded Word document, as seen in Trick #1.

Trick #6: kick start it all with a signed binary proxy execution

Be it in the end of the macros execution (for the macro-based delivery chain) or as a last step of the shortcut-embedded scripts (for the LNK-based delivery chain), DeathStalker leveraged a signed binary proxy execution to startup PowerPepper for the first time.

$ttss=Join-Path -path $src -ChildPath ('Startup'+[char]92+'StartPrinter.url'); 
start-process -filepath 'rundll32.exe' -argumentlist 
('ieframe.dll,openurl '.replace('openurl',('o').toupper()+'pen'+('url').toupper())+$ttss)

While the first (macro-based) delivery chain we retrieved fired the malicious VBS loader with “rundll32.exe ieadvpack.dll, RegisterOCX wscript.exe <script file> <script argument> pexe”, the recent ones use a “rundll32.exe ieframe.dll, OpenURL <Internet shortcut>” alternative combo. The latest rely on a dropped Internet shortcut file (.url), which will simply open a LNK launcher with a “file://” URL. The LNK launcher in turn runs the VBS loader (take a look at Trick #3).

PowerPepper’s targets geography

We of course cannot get a comprehensive view of all PowerPepper’s targets, but having tracked this implant starting May 2020, we managed to get a partial view of targeted countries before August 2020, as well as in November 2020.

Due to the very partial information we sometimes get for such research, and despite our efforts to filter as much as we can, we cannot rule out that some identified targets could actually be fellow researchers investigating the threat, or DeathStalker’s own testing infrastructure.

We could not precisely identify PowerPepper targets, but law and consultancy firms have been frequent actor’s targets.

Prevention and protection leads

In order to prevent successful PowerPepper execution or delivery, or to protect against associated infection chains, we could not but underline these usual and elementary defense measures:

  • Content hosters could regularly scan hosted files for malicious content, where regulations allows. They could protect their hosting infrastructure with endpoint protection software and traffic monitoring. They could also stack protections on privileged and remote accesses, with client network addresses filtering, multi-factors authentication (MFA), and authentication logs auditing.
  • Website owners and editors should frequently and responsively update their CMS backends as well as associated plugins. They could also stack protections on privileged and remote accesses, with client network addresses filtering, MFA and accesses logging on all backend endpoints.
  • Enterprise IT services should restrict scripts engines (i.e. PowerShell) use on end-users computers with enforced execution policies. They should setup endpoint protection software on end-users’ computers and content servers. They could allow DNS requests to corporate-managed resolvers and relays only, while filtering HTTP and DNS traffic at perimeter. Last but not least, they should train employees not to open attachments and links from unknown mail senders.
  • Individuals should never open Windows shortcuts that were downloaded from a remote location or attached to a mail, open attachments or click links in mails from unknown senders, or enable macros in documents from unverified source.


It only seems fair to write that DeathStalker tried hard to develop evasive, creative and intricate tools with this PowerPepper implant and associated delivery chains. Nothing is specifically sophisticated in techniques and tricks that are leveraged, yet the whole toolset proven itself to be effective, is pretty well put together, and shows determined efforts to compromise various targets around the world.

This is perfectly consistent with previous knowledge on DeathStalker actor, who demonstrated continuous capabilities to compromise targets since 2012, and to develop new implants and toolchains at fast pace. We discovered the PowerPepper implant in May 2020, and it has been regularly improved or adapted since then. At the same time, we also uncovered another previously unknown malware strain that we strongly believe is from the same actor, but however did not identify any Powersing-related activity since our previous article on DeathStalker in August 2020.

DeathStalker definitely is a threat to feel concerned about, as victimology for its various malware strains shows that any corporation or individual in the world could be targeted by their malicious activities, provided someone decided there is interest to, and passed them the word. Luckily for defenders, DeathStalker relied on a quite limited set of techniques to design its delivery chains until now, and implementing associated counter-measures is an attainable goal for most organizations.

Indicators of compromise

File hashes

IOC Description
A4DD981606EA0497BF9995F3BC672951 Malicious Word document (macro-based delivery chain)
871D64D8330D956593545DFFF069194E Malicious Word document (macro-based delivery chain)
81147EDFFAF63AE4068008C8235B34AF Malicious Windows shortcut (LNK-based delivery chain)
DFC2486DE9E0339A1B38BB4B9144EA83 Malicious Word document (downloaded by LNK-based delivery chain)
74D7DF2505471EADEB1CCFC48A238AEC Malicious CHM container
5019E29619469C74F2B826535C5A8BD8 Malicious CHM container
B4790E70B1297215E0875CFC2A56648E Malicious CHM container
3A6099214F474C1501C110CE66033F3C Malicious VBS Loader
07308FBC3D10FD476F1898ECF6762437 Malicious VBS Loader
1F77FBE4702F787A713D394B62D27B42 Malicious VBS Loader
6E99F6DA77B0620E89F6E88D91198C32 Malicious VBS Loader
5D04D246F3E5DA6A9347EC72494D5610 Malicious startup launcher LNK
BA7AE1C73A78D8DC4B3779BD6A151791 Malicious startup launcher LNK
1DC2B849A858BC479B1EF428491E0353 Malicious startup launcher LNK
9D4066C57C6E1602CE33F15DC7F3841B PowerPepper steganography image (peppers)
6FF8A3D18A6EA930E87AC364379ECEC2 PowerPepper steganography image (peppers)
871D64D8330D956593545DFFF069194E PowerPepper steganography image (peppers)
9CE299BBDD7FDBF9F30F8935C89D2877 PowerPepper steganography image (ferns)
34F086AE78C5319FB64BF1CAE8204D1B PowerPepper steganography image (ferns)

File paths

IOC Description
%PROGRAMDATA%\Support\licenseverification.vbs Malicious VBS Loader
%PROGRAMDATA%\Support\licenseverify.vbs Malicious VBS Loader
%PROGRAMDATA%\MyPrinter\NewFile.vbs Malicious VBS Loader
%PROGRAMDATA%\Printers\NewFile.vbs Malicious VBS Loader
%APPDATA %\Microsoft\Windows\Start Menu\Programs\Startup\System.lnk Malicious startup launcher LNK
%PROGRAMDATA%\MyPrinter\Web.lnk Malicious startup launcher LNK
%PROGRAMDATA%\Printers\Web.lnk Malicious startup launcher LNK
%APPDATA%\Roaming\Microsoft\Windows\Start Menu\Programs\StartUp\StartPrinter.url Malicious startup launcher URL

Domain and IPs

IOC Description
allmedicalpro[.]com PowerPepper C2 domain name
mediqhealthcare[.]com PowerPepper C2 domain name
gofinancesolutions[.]com PowerPepper C2 domain name
mailsigning.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)
mailsignature.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)
mailservice.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)
mailservices.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)
footersig.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)
globalsignature.pythonanywhere[.]com PowerPepper Signaling hostname (legitimate hoster and root domain)


IOC Description


PowerPepper Signaling hostname (legitimate but compromised Website)


hxxps://www.gsn-nettoyage[.]com/wp-snapshots/Quote 16 db room.docx

Malicious documents download location (legitimate but compromised Website)
hxxps://outlookusers.page[.]link/ Malicious documents download location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYdifkocKujNavvjY?e=hhuBV8 Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYdcbz1YwTJRkOxP4?e=u5wtbX Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYd1921tVEMKWaCUs?e=MyoVNF Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws /w/s!AvXRHBXCKmvYeFdjVtZN0Quljs4?e=dnA6GG Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYeePNerfsAWK0qVY?e=e4SsYM Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYejBpdekg1WUCM9M?e=UkhU10 Malicious document remote location (legitimate hoster and root domain)
hxxps://1drv[.]ws/w/s!AvXRHBXCKmvYe1ulhtazjNVvCqY?e=WptVTC Malicious document remote location (legitimate hoster and root domain)

Mail addresses

IOC Description
a.christy_inbox@outlook[.]com Suspected malicious spear-phishing mails sender (legitimate root domain)



More information: What did DeathStalker hide between two ferns?

Story added 3. December 2020, content source with full text you can find at link above.