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December 15, 2023

How Darktrace Halted A DarkGate in MS Teams

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15
Dec 2023
Discover how Darktrace thwarted DarkGate malware in Microsoft Teams. Stay informed on the latest cybersecurity measures and protect your business.

Securing Microsoft Teams and SharePoint

Given the prevalence of the Microsoft Teams and Microsoft SharePoint platforms in the workplace in recent years, it is essential that organizations stay vigilant to the threat posed by applications vital to hybrid and remote work and prioritize the security and cyber hygiene of these services. For just as the use of these platforms has increased exponentially with the rise of remote and hybrid working, so too has the malicious use of them to deliver malware to unassuming users.

Researchers across the threat landscape have begun to observe these legitimate services being leveraged by malicious actors as an initial access method. Microsoft Teams can easily be exploited to send targeted phishing messages to individuals within an organization, while appearing legitimate and safe. Although the exact contents of these messages may vary, the messages frequently use social engineering techniques to lure users to click on a SharePoint link embedded into the message. Interacting with the malicious link will then download a payload [1].

Darktrace observed one such malicious attempt to use Microsoft Teams and SharePoint in September 2023, when a device was observed downloading DarkGate, a commercial trojan that is known to deploy other strains of malware, also referred to as a commodity loader [2], after clicking on SharePoint link. Fortunately for the customer, Darktrace’s suite of products was perfectly poised to identify the initial signs of suspicious activity and Darktrace RESPOND™ was able to immediately halt the advancement of the attack.

DarkGate Attack Overview

On September 8, 2023, Darktrace DETECT™ observed around 30 internal devices on a customer network making unusual SSL connections to an external SharePoint site which contained the name of a person, 'XXXXXXXX-my.sharepoint[.]com' (107.136[.]8, 13.107.138[.]8). The organization did not have any employees who went by this name and prior to this activity, no internal devices had been seen contacting the endpoint.

At first glance, this initial attack vector would have appeared subtle and seemingly trustworthy to users. Malicious actors likely sent various users a phishing message via Microsoft Teams that contained the spoofed SharePoint link to the personalized SharePoint link ''XXXXXXXX-my.sharepoint[.]com'.

Figure 1: Advanced Search query showing a sudden spike in connections to ''XXXXXXXX -my.sharepoint[.]com'.

Darktrace observed around 10 devices downloading approximately 1 MB of data during their connections to the Sharepoint endpoint. Darktrace DETECT observed some of the devices making subsequent HTTP GET requests to a range of anomalous URIs. The devices utilized multiple user-agents for these connections, including ‘curl’, a command line tool that allows individuals to request and transfer data from a specific URL. The connections were made to the IP 5.188.87[.]58, an endpoint that has been flagged as an indicator of compromise (IoC) for DarkGate malware by multiple open-source intelligence (OSINT) sources [3], commonly associated with HTTP GET requests:

  1. GET request over port 2351 with the User-Agent header 'Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5)' and the target URI '/bfyxraav' to 5.188.87[.]58
  2. GET request over port 2351 with the user-agent header 'curl' and the target URI '/' to 5.188.87[.]58
  3. GET request over port 2351 with the user-agent header 'curl/8.0.1' and the target URI '/msibfyxraav' to 5.188.87[.]58

The HTTP GET requests made with the user-agent header 'curl' and the target URI '/' to 5.188.87[.]58 were responded to with a filename called 'Autoit3.exe'. The other requests received script files with names ending in '.au3, such as 'xkwtvq.au3', 'otxynh.au3', and 'dcthbq.au3'. DarkGate malware has been known to make use of legitimate AutoIt files, and typically runs multiple AutoIt scripts (‘.au3’) [4].

Following these unusual file downloads, the devices proceeded to make hundreds of HTTP POST requests to the target URI '/' using the user-agent header 'Mozilla/4.0 (compatible; Synapse)' to 5.188.87[.]58. The contents of these requests, along with the contents of the responses, appear to be heavily obfuscated.

Figure 2: Example of obfuscated response, as shown in a packet capture downloaded from Darktrace.

While Microsoft’s Safe Attachments and Safe Links settings were unable to detect this camouflaged malicious activity, Darktrace DETECT observed the unusual over-the-network connectivity that occurred. While Darktrace DETECT identified multiple internal devices engaging in this anomalous behavior throughout the course of the compromise, the activity observed on one device in particular best showcases the overall kill chain of this attack.

The device in question was observed using two different user agents (curl/8.0.1 and Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5)) when connecting to the endpoint 5.188.87[.]58 and target URI ‘/bfyxraav’. Additionally, Darktrace DETECT recognized that it was unusual for this device to be making these HTTP connections via destination port 2351.

As a result, Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the suspicious activity and was able to connect the unusual external connections together, viewing them as one beaconing incident as opposed to isolated series of connections.

Figure 3: Cyber AI Analyst investigation summarizing the unusual repeated connections made to 5.188.87[.]58 via destination port 2351.

Darktrace then observed the device downloading the ‘Autoit3.exe’ file. Darktrace RESPOND took swift mitigative action by blocking similar connections to this endpoint, preventing the device from downloading any additional suspicious files.

Figure 4: Suspicious ‘Autoit3.exe’ downloaded by the source device from the malicious external endpoint.

Just one millisecond later, Darktrace observed the device making suspicious HTTP GET requests to URIs including ‘/msibfyxraav’. Darktrace recognized that the device had carried out several suspicious actions within a relatively short period of time, breaching multiple DETECT models, indicating that it may have been compromised. As a result, RESPOND took action against the offending device by preventing it from communicating externally [blocking all outbound connections] for a period of one hour, allowing the customer’s security team precious time to address the issue.

It should be noted that, at this point, had the customer subscribed to Darktrace’s Proactive Threat Notification (PTN) service, the Darktrace Security Operations Center (SOC) would have investigated these incidents in greater detail, and likely would have sent a notification directly to the customer to inform them of the suspicious activity.

Additionally, AI Analyst collated various distinct events and suggested that these stages were linked as part of an attack. This type of augmented understanding of events calculated at machine speed is extremely valuable since it likely would have taken a human analyst hours to link all the facets of the incident together.  

Figure 5: AI Analyst investigation showcasing the use of the ‘curl’ user agent to connect to the target URI ‘/msibfyxraav’.
Figure 6: Darktrace RESPOND moved to mitigate any following connections by blocking all outgoing traffic for 1 hour.

Following this, an automated investigation was launched by Microsoft Defender for Endpoint. Darktrace is designed to coordinate with multiple third-party security tools, allowing for information on ongoing incidents to be seamlessly exchanged between Darktrace and other security tools. In this instance, Microsoft Defender identified a ‘low severity’ incident on the device, this automatically triggered a corresponding alert within DETECT, presented on the Darktrace Threat Visuallizer.

The described activity occurred within milliseconds. At each step of the attack, Darktrace RESPOND took action either by enforcing expected patterns of life [normality] on the affected device, blocking connections to suspicious endpoints for a specified amount of time, and/or blocking all outgoing traffic from the device. All the relevant activity was detected and promptly stopped for this device, and other compromised devices, thus containing the compromise and providing the security team invaluable remediation time.

Figure 7: Overview of the compromise activity, all of which took place within a matter of miliseconds.

Darktrace identified similar activity on other devices in this customer’s network, as well as across Darktrace’s fleet around the same time in early September.

On a different customer environment, Darktrace DETECT observed more than 25 ‘.au3’ files being downloaded; this activity can be seen in Figure 9.

Figure 8: High volume of file downloads following GET request and 'curl' commands.

Figure 9 provides more details of this activity, including the source and destination IP addresses (5.188.87[.]58), the destination port, the HTTP method used and the MIME/content-type of the file

Figure 9: Additional information of the anomalous connections.

A compromised server in another customer deployment was seen establishing unusual connections to the external IP address 80.66.88[.]145 – an endpoint that has been associated with DarkGate by OSINT sources [5]. This activity was identified by Darktrace/DETECT as a new connection for the device via an unusual destination port, 2840. As the device in question was a critical server, Darktrace DETECT treated it with suspicion and generated an ‘Anomalous External Activity from Critical Network Device’ model breach.  

Figure 10: Model breach and model breach event log for suspicious connections to additional endpoint.

Conclusion

While Microsoft Teams and SharePoint are extremely prominent tools that are essential to the business operations of many organizations, they can also be used to compromise via living off the land, even at initial intrusion. Any Microsoft Teams user within a corporate setting could be targeted by a malicious actor, as such SharePoint links from unknown senders should always be treated with caution and should not automatically be considered as secure or legitimate, even when operating within legitimate Microsoft infrastructure.

Malicious actors can leverage these commonly used platforms as a means to carry out their cyber-attacks, therefore organizations must take appropriate measures to protect and secure their digital environments. As demonstrated here, threat actors can attempt to deploy malware, like DarkGate, by targeting users with spoofed Microsoft Teams messages. By masking malicious links as legitimate SharePoint links, these attempts can easily convince targets and bypass traditional security tools and even Microsoft’s own Safe Links and Safe Attachments security capabilities.

When the chain of events of an attack escalates within milliseconds, organizations must rely on AI-driven tools that can quickly identify and automatically respond to suspicious events without latency. As such, the value of Darktrace DETECT and Darktrace RESPOND cannot be overstated. Given the efficacy and efficiency of Darktrace’s detection and autonomous response capabilities, a more severe network compromise in the form of the DarkGate commodity loader was ultimately averted.

Credit to Natalia Sánchez Rocafort, Cyber Security Analyst, Zoe Tilsiter.

Appendices

Darktrace DETECT Model Detections

  • [Model Breach: Device / Initial Breach Chain Compromise 100% –– Breach URI: /#modelbreach/114039 ] (Enhanced Monitoring)·      [Model Breach: Device / Initial Breach Chain Compromise 100% –– Breach URI: /#modelbreach/114124 ] (Enhanced Monitoring)
  • [Model Breach: Device / New User Agent and New IP 62% –– Breach URI: /#modelbreach/114030 ]
  • [Model Breach: Anomalous Connection / Application Protocol on Uncommon Port 46% –– Breach URI: /#modelbreach/114031 ]
  • [Model Breach: Anomalous Connection / New User Agent to IP Without Hostname 62% –– Breach URI: /#modelbreach/114032 ]
  • [Model Breach: Device / New User Agent 32% –– Breach URI: /#modelbreach/114035 ]
  • [Model Breach: Device / Three Or More New User Agents 31% –– Breach URI: /#modelbreach/114036 ]
  • [Model Breach: Anomalous Server Activity / Anomalous External Activity from Critical Network Device 62% –– Breach URI: /#modelbreach/612173 ]
  • [Model Breach: Anomalous File / EXE from Rare External Location 61% –– Breach URI: /#modelbreach/114037 ]
  • [Model Breach: Anomalous Connection / Multiple Connections to New External TCP Port 61% –– Breach URI: /#modelbreach/114042 ]
  • [Model Breach: Security Integration / Integration Ransomware Detected 100% –– Breach URI: /#modelbreach/114049 ]
  • [Model Breach: Compromise / Beaconing Activity To External Rare 62% –– Breach URI: /#modelbreach/114059 ]
  • [Model Breach: Compromise / HTTP Beaconing to New Endpoint 30% –– Breach URI: /#modelbreach/114067 ]
  • [Model Breach: Security Integration / C2 Activity and Integration Detection 100% –– Breach URI: /#modelbreach/114069 ]
  • [Model Breach: Anomalous File / EXE from Rare External Location 55% –– Breach URI: /#modelbreach/114077 ]
  • [Model Breach: Compromise / High Volume of Connections with Beacon Score 66% –– Breach URI: /#modelbreach/114260 ]
  • [Model Breach: Security Integration / Low Severity Integration Detection 59% –– Breach URI: /#modelbreach/114293 ]
  • [Model Breach: Security Integration / Low Severity Integration Detection 33% –– Breach URI: /#modelbreach/114462 ]
  • [Model Breach: Security Integration / Integration Ransomware Detected 100% –– Breach URI: /#modelbreach/114109 ]·      [Model Breach: Device / Three Or More New User Agents 31% –– Breach URI: /#modelbreach/114118 ]·      [Model Breach: Anomalous Connection / Application Protocol on Uncommon Port 46% –– Breach URI: /#modelbreach/114113 ] ·      [Model Breach: Anomalous Connection / New User Agent to IP Without Hostname 62% –– Breach URI: /#modelbreach/114114 ]·      [Model Breach: Device / New User Agent 32% –– Breach URI: /#modelbreach/114117 ]·      [Model Breach: Anomalous File / EXE from Rare External Location 61% –– Breach URI: /#modelbreach/114122 ]·      [Model Breach: Security Integration / Low Severity Integration Detection 54% –– Breach URI: /#modelbreach/114310 ]
  • [Model Breach: Security Integration / Integration Ransomware Detected 65% –– Breach URI: /#modelbreach/114662 ]Darktrace/Respond Model Breaches
  • [Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 61% –– Breach URI: /#modelbreach/114033 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena File then New Outbound Block 100% –– Breach URI: /#modelbreach/114038 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block 100% –– Breach URI: /#modelbreach/114040 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block 87% –– Breach URI: /#modelbreach/114041 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach 87% –– Breach URI: /#modelbreach/114043 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 100% –– Breach URI: /#modelbreach/114052 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Security Integration and Network Activity Block 87% –– Breach URI: /#modelbreach/114070 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 87% –– Breach URI: /#modelbreach/114071 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena Suspicious Activity Block 87% –– Breach URI: /#modelbreach/114072 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 53% –– Breach URI: /#modelbreach/114079 ]
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 64% –– Breach URI: /#modelbreach/114539 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 66% –– Breach URI: /#modelbreach/114667 ]
  • [Model Breach: Antigena / Network::External Threat::Antigena Suspicious Activity Block 79% –– Breach URI: /#modelbreach/114684 ]·      
  • [Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 100% –– Breach URI: /#modelbreach/114110 ]·      
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block 87% –– Breach URI: /#modelbreach/114111 ]·      
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach 87% –– Breach URI: /#modelbreach/114115 ]·      
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 87% –– Breach URI: /#modelbreach/114116 ]·      
  • [Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 61% –– Breach URI: /#modelbreach/114121 ]·      
  • [Model Breach: Antigena / Network::External Threat::Antigena File then New Outbound Block 100% –– Breach URI: /#modelbreach/114123 ]·      
  • [Model Breach: Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block 100% –– Breach URI: /#modelbreach/114125 ]

List of IoCs

IoC - Type - Description + Confidence

5.188.87[.]58 - IP address - C2 endpoint

80.66.88[.]145 - IP address - C2 endpoint

/bfyxraav - URI - Possible C2 endpoint URI

/msibfyxraav - URI - Possible C2 endpoint URI

Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5) - User agent - Probable user agent leveraged

curl - User agent - Probable user agent leveraged

curl/8.0.1 - User agent - Probable user agent leveraged

Mozilla/4.0 (compatible; Synapse) - User agent - Probable user agent leveraged

Autoit3.exe - Filename - Exe file

CvUYLoTv.au3    

eDVeqcCe.au3

FeLlcFRS.au3

FTEZlGhe.au3

HOrzcEWV.au3

rKlArXHH.au3

SjadeWUz.au3

ZgOLxJQy.au3

zSrxhagw.au3

ALOXitYE.au3

DKRcfZfV.au3

gQZVKzek.au3

JZrvmJXK.au3

kLECCtMw.au3

LEXCjXKl.au3

luqWdAzF.au3

mUBNrGpv.au3

OoCdHeJT.au3

PcEJXfIl.au3

ssElzrDV.au3

TcBwRRnp.au3

TFvAUIgu.au3

xkwtvq.au3

otxynh.au3

dcthbq.au3 - Filenames - Possible exe files delivered in response to curl/8.0.1 GET requests with Target URI '/msibfyxraav

f3a0a85fe2ea4a00b3710ef4833b07a5d766702b263fda88101e0cb804d8c699 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

afa3feea5964846cd436b978faa7d31938e666288ffaa75d6ba75bfe6c12bf61 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

63aeac3b007436fa8b7ea25298362330423b80a4cb9269fd2c3e6ab1b1289208 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

ab6704e836a51555ec32d1ff009a79692fa2d11205f9b4962121bda88ba55486 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

References

1. https://www.truesec.com/hub/blog/darkgate-loader-delivered-via-teams

2. https://feedit.cz/wp-content/uploads/2023/03/YiR2022_onepager_ransomware_loaders.pdf

3. https://www.virustotal.com/gui/ip-address/5.188.87[.]58

4. https://www.forescout.com/resources/darkgate-loader-malspam-campaign/

5. https://otx.alienvault.com/indicator/ip/80.66.88[.]145

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
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Natalia Sánchez Rocafort
Cyber Security Analyst
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March 18, 2025

Survey findings: How is AI Impacting the SOC?

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There’s no question that AI is already impacting the SOC – augmenting, assisting, and filling the gaps left by staff and skills shortages. We surveyed over 1,500 cybersecurity professionals from around the world to uncover their attitudes to AI cybersecurity in 2025. Our findings revealed striking trends in how AI is changing the way security leaders think about hiring and SOC transformation. Download the full report for the big picture, available now.

Download the full report to explore these findings in depth

The AI-human conundrum

Let’s start with some context. As the cybersecurity sector has rapidly evolved to integrate AI into all elements of cyber defense, the pace of technological advancement is outstripping the development of necessary skills. Given the ongoing challenges in security operations, such as employee burnout, high turnover rates, and talent shortages, recruiting personnel to bridge these skills gaps remains an immense challenge in today’s landscape.

But here, our main findings on this topic seem to contradict each other.

There’s no question over the impact of AI-powered threats – nearly three-quarters (74%) agree that AI-powered threats now pose a significant challenge for their organization.  

When we look at how security leaders are defending against AI-powered threats, over 3 out of 5 (62%) see insufficient personnel to manage tools and alerts as the biggest barrier.  

Yet at the same time, increasing cyber security staff is at the bottom of the priority list for survey participants, with only 11% planning to increase cybersecurity staff in 2025 – less than in 2024. What 64% of stakeholders are committed to, however, is adding new AI-powered tools onto their existing security stacks.

The conclusion? Due to pressures around hiring, defensive AI is becoming integral to the SOC as a means of augmenting understaffed teams.

How is AI plugging skills shortages in the SOC?

As explored in our recent white paper, the CISO’s Guide to Navigating the Cybersecurity Skills Shortage, 71% of organizations report unfilled cybersecurity positions, leading to the estimation that less than 10% of alerts are thoroughly vetted. In this scenario, AI has become an essential multiplier to relieve the burden on security teams.

95% of respondents agree that AI-powered solutions can significantly improve the speed and efficiency of their defenses. But how?

The area security leaders expect defensive AI to have the biggest impact is on improving threat detection, followed by autonomous response to threats and identifying exploitable vulnerabilities.

Interestingly, the areas that participants ranked less highly (reducing alert fatigue and running phishing simulation), are the tasks that AI already does well and can therefore be used already to relieve the burden of manual, repetitive work on the SOC.

Different perspectives from different sides of the SOC

CISOs and SecOps teams aren’t necessarily aligned on the AI defense question – while CISOs tend to see it as a strategic game-changer, SecOps teams on the front lines may be more sceptical, wary of its real-world reliability and integration into workflows.  

From the data, we see that while less than a quarter of execs doubt that AI-powered solutions will block and automatically respond to AI threats, about half of SecOps aren’t convinced. And only 17% of CISOs lack confidence in the ability of their teams to implement and use AI-powered solutions, whereas over 40% those in the team doubt their own ability to do so.

This gap feeds into the enthusiasm that executives share about adding AI-driven tools into the stack, while day-to-day users of the tools are more interested in improving security awareness training and improving cybersecurity tool integration.

Levels of AI understanding in the SOC

AI is only as powerful as the people who use it, and levels of AI expertise in the SOC can make or break its real-world impact. If security leaders want to unlock AI’s full potential, they must bridge the knowledge gap—ensuring teams understand not just the different types of AI, but where it can be applied for maximum value.

Only 42% of security professionals are confident that they fully understand all the types of AI in their organization’s security stack.

This data varies between job roles – executives report higher levels of understanding (60% say they know exactly which types of AI are being used) than participants in other roles. Despite having a working knowledge of using the tools day-to-day, SecOps practitioners were more likely to report having a “reasonable understanding” of the types of AI in use in their organization (42%).  

Whether this reflects a general confidence in executives rather than technical proficiency it’s hard to say, but it speaks to the importance of AI-human collaboration – introducing AI tools for cybersecurity to plug the gaps in human teams will only be effective if security professionals are supported with the correct education and training.  

Download the full report to explore these findings in depth

The full report for Darktrace’s State of AI Cybersecurity is out now. Download the paper to dig deeper into these trends, and see how results differ by industry, region, organization size, and job title.  

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March 18, 2025

Darktrace's Detection of State-Linked ShadowPad Malware

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An integral part of cybersecurity is anomaly detection, which involves identifying unusual patterns or behaviors in network traffic that could indicate malicious activity, such as a cyber-based intrusion. However, attribution remains one of the ever present challenges in cybersecurity. Attribution involves the process of accurately identifying and tracing the source to a specific threat actor(s).

Given the complexity of digital networks and the sophistication of attackers who often use proxies or other methods to disguise their origin, pinpointing the exact source of a cyberattack is an arduous task. Threat actors can use proxy servers, botnets, sophisticated techniques, false flags, etc. Darktrace’s strategy is rooted in the belief that identifying behavioral anomalies is crucial for identifying both known and novel threat actor campaigns.

The ShadowPad cluster

Between July 2024 and November 2024, Darktrace observed a cluster of activity threads sharing notable similarities. The threads began with a malicious actor using compromised user credentials to log in to the target organization's Check Point Remote Access virtual private network (VPN) from an attacker-controlled, remote device named 'DESKTOP-O82ILGG'.  In one case, the IP from which the initial login was carried out was observed to be the ExpressVPN IP address, 194.5.83[.]25. After logging in, the actor gained access to service account credentials, likely via exploitation of an information disclosure vulnerability affecting Check Point Security Gateway devices. Recent reporting suggests this could represent exploitation of CVE-2024-24919 [27,28]. The actor then used these compromised service account credentials to move laterally over RDP and SMB, with files related to the modular backdoor, ShadowPad, being delivered to the  ‘C:\PerfLogs\’ directory of targeted internal systems. ShadowPad was seen communicating with its command-and-control (C2) infrastructure, 158.247.199[.]185 (dscriy.chtq[.]net), via both HTTPS traffic and DNS tunneling, with subdomains of the domain ‘cybaq.chtq[.]net’ being used in the compromised devices’ TXT DNS queries.

Darktrace’s Advanced Search data showing the VPN-connected device initiating RDP connections to a domain controller (DC). The device subsequently distributes likely ShadowPad-related payloads and makes DRSGetNCChanges requests to a second DC.
Figure 1: Darktrace’s Advanced Search data showing the VPN-connected device initiating RDP connections to a domain controller (DC). The device subsequently distributes likely ShadowPad-related payloads and makes DRSGetNCChanges requests to a second DC.
Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.
Figure 2: Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.

Darktrace observed these ShadowPad activity threads within the networks of European-based customers in the manufacturing and financial sectors.  One of these intrusions was followed a few months later by likely state-sponsored espionage activity, as detailed in the investigation of the year in Darktrace’s Annual Threat Report 2024.

Related ShadowPad activity

Additional cases of ShadowPad were observed across Darktrace’s customer base in 2024. In some cases, common C2 infrastructure with the cluster discussed above was observed, with dscriy.chtq[.]net and cybaq.chtq[.]net both involved; however, no other common features were identified. These ShadowPad infections were observed between April and November 2024, with customers across multiple regions and sectors affected.  Darktrace’s observations align with multiple other public reports that fit the timeframe of this campaign.

Darktrace has also observed other cases of ShadowPad without common infrastructure since September 2024, suggesting the use of this tool by additional threat actors.

The data theft thread

One of the Darktrace customers impacted by the ShadowPad cluster highlighted above was a European manufacturer. A distinct thread of activity occurred within this organization’s network several months after the ShadowPad intrusion, in October 2024.

The thread involved the internal distribution of highly masqueraded executable files via Sever Message Block (SMB) and WMI (Windows Management Instrumentation), the targeted collection of sensitive information from an internal server, and the exfiltration of collected information to a web of likely compromised sites. This observed thread of activity, therefore, consisted of three phrases: lateral movement, collection, and exfiltration.

The lateral movement phase began when an internal user device used an administrative credential to distribute files named ‘ProgramData\Oracle\java.log’ and 'ProgramData\Oracle\duxwfnfo' to the c$ share on another internal system.  

Darktrace model alert highlighting an SMB write of a file named ‘ProgramData\Oracle\java.log’ to the c$ share on another device.
Figure 3: Darktrace model alert highlighting an SMB write of a file named ‘ProgramData\Oracle\java.log’ to the c$ share on another device.

Over the next few days, Darktrace detected several other internal systems using administrative credentials to upload files with the following names to the c$ share on internal systems:

ProgramData\Adobe\ARM\webservices.dll

ProgramData\Adobe\ARM\wksprt.exe

ProgramData\Oracle\Java\wksprt.exe

ProgramData\Oracle\Java\webservices.dll

ProgramData\Microsoft\DRM\wksprt.exe

ProgramData\Microsoft\DRM\webservices.dll

ProgramData\Abletech\Client\webservices.dll

ProgramData\Abletech\Client\client.exe

ProgramData\Adobe\ARM\rzrmxrwfvp

ProgramData\3Dconnexion\3DxWare\3DxWare.exe

ProgramData\3Dconnexion\3DxWare\webservices.dll

ProgramData\IDMComp\UltraCompare\updater.exe

ProgramData\IDMComp\UltraCompare\webservices.dll

ProgramData\IDMComp\UltraCompare\imtrqjsaqmm

Cyber AI Analyst highlighting an SMB write of a file named ‘ProgramData\Adobe\ARM\webservices.dll’ to the c$ share on an internal system.
Figure 4: Cyber AI Analyst highlighting an SMB write of a file named ‘ProgramData\Adobe\ARM\webservices.dll’ to the c$ share on an internal system.

The threat actor appears to have abused the Microsoft RPC (MS-RPC) service, WMI, to execute distributed payloads, as evidenced by the ExecMethod requests to the IWbemServices RPC interface which immediately followed devices’ SMB uploads.  

Cyber AI Analyst data highlighting a thread of activity starting with an SMB data upload followed by ExecMethod requests.
Figure 5: Cyber AI Analyst data highlighting a thread of activity starting with an SMB data upload followed by ExecMethod requests.

Several of the devices involved in these lateral movement activities, both on the source and destination side, were subsequently seen using administrative credentials to download tens of GBs of sensitive data over SMB from a specially selected server.  The data gathering stage of the threat sequence indicates that the threat actor had a comprehensive understanding of the organization’s system architecture and had precise objectives for the information they sought to extract.

Immediately after collecting data from the targeted server, devices went on to exfiltrate stolen data to multiple sites. Several other likely compromised sites appear to have been used as general C2 infrastructure for this intrusion activity. The sites used by the threat actor for C2 and data exfiltration purport to be sites for companies offering a variety of service, ranging from consultancy to web design.

Screenshot of one of the likely compromised sites used in the intrusion. 
Figure 6: Screenshot of one of the likely compromised sites used in the intrusion.

At least 16 sites were identified as being likely data exfiltration or C2 sites used by this threat actor in their operation against this organization. The fact that the actor had such a wide web of compromised sites at their disposal suggests that they were well-resourced and highly prepared.  

Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.
Figure 7: Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.
Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com    
Figure 8: Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com  

Cyber AI Analyst spotlight

Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.
Figure 9: Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.  
Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.
Figure 10: Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.

As shown in the above figures, Cyber AI Analyst’s ability to thread together the different steps of these attack chains are worth highlighting.

In the ShadowPad attack chains, Cyber AI Analyst was able to identify SMB writes from the VPN subnet to the DC, and the C2 connections from the DC. It was also able to weave together this activity into a single thread representing the attacker’s progression.

Similarly, in the data exfiltration attack chain, Cyber AI Analyst identified and connected multiple types of lateral movement over SMB and WMI and external C2 communication to various external endpoints, linking them in a single, connected incident.

These Cyber AI Analyst actions enabled a quicker understanding of the threat actor sequence of events and, in some cases, faster containment.

Attribution puzzle

Publicly shared research into ShadowPad indicates that it is predominantly used as a backdoor in People’s Republic of China (PRC)-sponsored espionage operations [5][6][7][8][9][10]. Most publicly reported intrusions involving ShadowPad  are attributed to the China-based threat actor, APT41 [11][12]. Furthermore, Google Threat Intelligence Group (GTIG) recently shared their assessment that ShadowPad usage is restricted to clusters associated with APT41 [13]. Interestingly, however, there have also been public reports of ShadowPad usage in unattributed intrusions [5].

The data theft activity that later occurred in the same Darktrace customer network as one of these ShadowPad compromises appeared to be the targeted collection and exfiltration of sensitive data. Such an objective indicates the activity may have been part of a state-sponsored operation. The tactics, techniques, and procedures (TTPs), artifacts, and C2 infrastructure observed in the data theft thread appear to resemble activity seen in previous Democratic People’s Republic of Korea (DPRK)-linked intrusion activities [15] [16] [17] [18] [19].

The distribution of payloads to the following directory locations appears to be a relatively common behavior in DPRK-sponsored intrusions.

Observed examples:

C:\ProgramData\Oracle\Java\  

C:\ProgramData\Adobe\ARM\  

C:\ProgramData\Microsoft\DRM\  

C:\ProgramData\Abletech\Client\  

C:\ProgramData\IDMComp\UltraCompare\  

C:\ProgramData\3Dconnexion\3DxWare\

Additionally, the likely compromised websites observed in the data theft thread, along with some of the target URI patterns seen in the C2 communications to these sites, resemble those seen in previously reported DPRK-linked intrusion activities.

No clear evidence was found to link the ShadowPad compromise to the subsequent data theft activity that was observed on the network of the manufacturing customer. It should be noted, however, that no clear signs of initial access were found for the data theft thread – this could suggest the ShadowPad intrusion itself represents the initial point of entry that ultimately led to data exfiltration.

Motivation-wise, it seems plausible for the data theft thread to have been part of a DPRK-sponsored operation. DPRK is known to pursue targets that could potentially fulfil its national security goals and had been publicly reported as being active in months prior to this intrusion [21]. Furthermore, the timing of the data theft aligns with the ratification of the mutual defense treaty between DPRK and Russia and the subsequent accused activities [20].

Darktrace assesses with medium confidence that a nation-state, likely DPRK, was responsible, based on our investigation, the threat actor applied resources, patience, obfuscation, and evasiveness combined with external reporting, collaboration with the cyber community, assessing the attacker’s motivation and world geopolitical timeline, and undisclosed intelligence.

Conclusion

When state-linked cyber activity occurs within an organization’s environment, previously unseen C2 infrastructure and advanced evasion techniques will likely be used. State-linked cyber actors, through their resources and patience, are able to bypass most detection methods, leaving anomaly-based methods as a last line of defense.

Two threads of activity were observed within Darktrace’s customer base over the last year: The first operation involved the abuse of Check Point VPN credentials to log in remotely to organizations’ networks, followed by the distribution of ShadowPad to an internal domain controller. The second operation involved highly targeted data exfiltration from the network of one of the customers impacted by the previously mentioned ShadowPad activity.

Despite definitive attribution remaining unresolved, both the ShadowPad and data exfiltration activities were detected by Darktrace’s Self-Learning AI, with Cyber AI Analyst playing a significant role in identifying and piecing together the various steps of the intrusion activities.  

Credit to Sam Lister (R&D Detection Analyst), Emma Foulger (Principal Cyber Analyst), Nathaniel Jones (VP), and the Darktrace Threat Research team.

Appendices

Darktrace / NETWORK model alerts

User / New Admin Credentials on Client

Anomalous Connection / Unusual Admin SMB Session

Compliance / SMB Drive Write  

Device / Anomalous SMB Followed By Multiple Model Breaches

Anomalous File / Internal / Unusual SMB Script Write

User / New Admin Credentials on Client  

Anomalous Connection / Unusual Admin SMB Session

Compliance / SMB Drive Write

Device / Anomalous SMB Followed By Multiple Model Breaches

Anomalous File / Internal / Unusual SMB Script Write

Device / New or Uncommon WMI Activity

Unusual Activity / Internal Data Transfer

Anomalous Connection / Download and Upload

Anomalous Server Activity / Rare External from Server

Compromise / Beacon to Young Endpoint

Compromise / Agent Beacon (Short Period)

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Connection / POST to PHP on New External Host

Compromise / Sustained SSL or HTTP Increase

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Device / Multiple C2 Model Alerts

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Download and Upload

Unusual Activity / Unusual External Data Transfer

Anomalous Connection / Low and Slow Exfiltration

Anomalous Connection / Uncommon 1 GiB Outbound  

MITRE ATT&CK mapping

(Technique name – Tactic ID)

ShadowPad malware threads

Initial Access - Valid Accounts: Domain Accounts (T1078.002)

Initial Access - External Remote Services (T1133)

Privilege Escalation - Exploitation for Privilege Escalation (T1068)

Privilege Escalation - Valid Accounts: Default Accounts (T1078.001)

Defense Evasion - Masquerading: Match Legitimate Name or Location (T1036.005)

Lateral Movement - Remote Services: Remote Desktop Protocol (T1021.001)

Lateral Movement - Remote Services: SMB/Windows Admin Shares (T1021.002)

Command and Control - Proxy: Internal Proxy (T1090.001)

Command and Control - Application Layer Protocol: Web Protocols (T1071.001)

Command and Control - Encrypted Channel: Asymmetric Cryptography (T1573.002)

Command and Control - Application Layer Protocol: DNS (T1071.004)

Data theft thread

Resource Development - Compromise Infrastructure: Domains (T1584.001)

Privilege Escalation - Valid Accounts: Default Accounts (T1078.001)

Privilege Escalation - Valid Accounts: Domain Accounts (T1078.002)

Execution - Windows Management Instrumentation (T1047)

Defense Evasion - Masquerading: Match Legitimate Name or Location (T1036.005)

Defense Evasion - Obfuscated Files or Information (T1027)

Lateral Movement - Remote Services: SMB/Windows Admin Shares (T1021.002)

Collection - Data from Network Shared Drive (T1039)

Command and Control - Application Layer Protocol: Web Protocols (T1071.001)

Command and Control - Encrypted Channel: Asymmetric Cryptography (T1573.002)

Command and Control - Proxy: External Proxy (T1090.002)

Exfiltration - Exfiltration Over C2 Channel (T1041)

Exfiltration - Data Transfer Size Limits (T1030)

List of indicators of compromise (IoCs)

IP addresses and/or domain names (Mid-high confidence):

ShadowPad thread

- dscriy.chtq[.]net • 158.247.199[.]185 (endpoint of C2 comms)

- cybaq.chtq[.]net (domain name used for DNS tunneling)  

Data theft thread

- yasuconsulting[.]com (45.158.12[.]7)

- hobivan[.]net (94.73.151[.]72)

- mediostresbarbas.com[.]ar (75.102.23[.]3)

- mnmathleague[.]org (185.148.129[.]24)

- goldenborek[.]com (94.138.200[.]40)

- tunemmuhendislik[.]com (94.199.206[.]45)

- anvil.org[.]ph (67.209.121[.]137)

- partnerls[.]pl (5.187.53[.]50)

- angoramedikal[.]com (89.19.29[.]128)

- awork-designs[.]dk (78.46.20[.]225)

- digitweco[.]com (38.54.95[.]190)

- duepunti-studio[.]it (89.46.106[.]61)

- scgestor.com[.]br (108.181.92[.]71)

- lacapannadelsilenzio[.]it (86.107.36[.]15)

- lovetamagotchith[.]com (203.170.190[.]137)

- lieta[.]it (78.46.146[.]147)

File names (Mid-high confidence):

ShadowPad thread:

- perflogs\1.txt

- perflogs\AppLaunch.exe

- perflogs\F4A3E8BE.tmp

- perflogs\mscoree.dll

Data theft thread

- ProgramData\Oracle\java.log

- ProgramData\Oracle\duxwfnfo

- ProgramData\Adobe\ARM\webservices.dll

- ProgramData\Adobe\ARM\wksprt.exe

- ProgramData\Oracle\Java\wksprt.exe

- ProgramData\Oracle\Java\webservices.dll

- ProgramData\Microsoft\DRM\wksprt.exe

- ProgramData\Microsoft\DRM\webservices.dll

- ProgramData\Abletech\Client\webservices.dll

- ProgramData\Abletech\Client\client.exe

- ProgramData\Adobe\ARM\rzrmxrwfvp

- ProgramData\3Dconnexion\3DxWare\3DxWare.exe

- ProgramData\3Dconnexion\3DxWare\webservices.dll

- ProgramData\IDMComp\UltraCompare\updater.exe

- ProgramData\IDMComp\UltraCompare\webservices.dll

- ProgramData\IDMComp\UltraCompare\imtrqjsaqmm

- temp\HousecallLauncher64.exe

Attacker-controlled device hostname (Mid-high confidence)

- DESKTOP-O82ILGG

References  

[1] https://www.kaspersky.com/about/press-releases/shadowpad-how-attackers-hide-backdoor-in-software-used-by-hundreds-of-large-companies-around-the-world  

[2] https://media.kasperskycontenthub.com/wp-content/uploads/sites/43/2017/08/07172148/ShadowPad_technical_description_PDF.pdf

[3] https://blog.avast.com/new-investigations-in-ccleaner-incident-point-to-a-possible-third-stage-that-had-keylogger-capacities

[4] https://securelist.com/operation-shadowhammer-a-high-profile-supply-chain-attack/90380/

[5] https://assets.sentinelone.com/c/Shadowpad?x=P42eqA

[6] https://www.cyfirma.com/research/the-origins-of-apt-41-and-shadowpad-lineage/

[7] https://www.csoonline.com/article/572061/shadowpad-has-become-the-rat-of-choice-for-several-state-sponsored-chinese-apts.html

[8] https://global.ptsecurity.com/analytics/pt-esc-threat-intelligence/shadowpad-new-activity-from-the-winnti-group

[9] https://cymulate.com/threats/shadowpad-privately-sold-malware-espionage-tool/

[10] https://www.secureworks.com/research/shadowpad-malware-analysis

[11] https://blog.talosintelligence.com/chinese-hacking-group-apt41-compromised-taiwanese-government-affiliated-research-institute-with-shadowpad-and-cobaltstrike-2/

[12] https://hackerseye.net/all-blog-items/tails-from-the-shadow-apt-41-injecting-shadowpad-with-sideloading/

[13] https://cloud.google.com/blog/topics/threat-intelligence/scatterbrain-unmasking-poisonplug-obfuscator

[14] https://www.domaintools.com/wp-content/uploads/conceptualizing-a-continuum-of-cyber-threat-attribution.pdf

[15] https://www.nccgroup.com/es/research-blog/north-korea-s-lazarus-their-initial-access-trade-craft-using-social-media-and-social-engineering/  

[16] https://www.microsoft.com/en-us/security/blog/2021/01/28/zinc-attacks-against-security-researchers/

[17] https://www.microsoft.com/en-us/security/blog/2022/09/29/zinc-weaponizing-open-source-software/  

[18] https://www.welivesecurity.com/en/eset-research/lazarus-luring-employees-trojanized-coding-challenges-case-spanish-aerospace-company/  

[19] https://blogs.jpcert.or.jp/en/2021/01/Lazarus_malware2.html  

[20] https://usun.usmission.gov/joint-statement-on-the-unlawful-arms-transfer-by-the-democratic-peoples-republic-of-korea-to-russia/

[21] https://media.defense.gov/2024/Jul/25/2003510137/-1/-1/1/Joint-CSA-North-Korea-Cyber-Espionage-Advance-Military-Nuclear-Programs.PDF  

[22] https://kyivindependent.com/first-north-korean-troops-deployed-to-front-line-in-kursk-oblast-ukraines-military-intelligence-says/

[23] https://www.microsoft.com/en-us/security/blog/2024/12/04/frequent-freeloader-part-i-secret-blizzard-compromising-storm-0156-infrastructure-for-espionage/  

[24] https://www.microsoft.com/en-us/security/blog/2024/12/11/frequent-freeloader-part-ii-russian-actor-secret-blizzard-using-tools-of-other-groups-to-attack-ukraine/  

[25] https://www.sentinelone.com/labs/chamelgang-attacking-critical-infrastructure-with-ransomware/    

[26] https://thehackernews.com/2022/06/state-backed-hackers-using-ransomware.html/  

[27] https://blog.checkpoint.com/security/check-point-research-explains-shadow-pad-nailaolocker-and-its-protection/

[28] https://www.orangecyberdefense.com/global/blog/cert-news/meet-nailaolocker-a-ransomware-distributed-in-europe-by-shadowpad-and-plugx-backdoors

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About the author
Sam Lister
SOC Analyst
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