Attack Trends: VIP Impersonation in the Business Hierarchy
22
Feb 2024
VIP Impersonation occurs when a cyber-threat actor impersonates a prominent employee to obtain sensitive data. Learn all about VIP impersonation here.
What is VIP impersonation?
VIP impersonation involves a threat actor impersonating a trusted, prominent figure at an organization in an attempt to solicit sensitive information from an employee.
VIP impersonation is a high-priority issue for security teams, but it can be difficult to assess the exact risks, and whether those are more critical than other types of compromise. Looking across a range of Darktrace/Email™ customer deployments, this blog explores the patterns of individuals targeted for impersonation and evaluates if these target priorities correspond with security teams' focus on protecting attack pathways to critical assets.
How do security teams stop VIP Impersonation?
Protecting VIP entities within an organization has long been a traditional focus for security teams. The assumption is that VIPs, due to their prominence, possess the greatest access to critical assets, making them prime targets for cyber threats.
Email remains the predominant vector for attacks, with over 90% of breaches originating from malicious emails. However, the dynamics of email-based attacks are shifting, as the widespread use of generative AI is lowering the barrier to entry by allowing adversaries to create hyper-realistic emails with minimal errors.
Given these developments, it's worth asking the question – which entities (VIP/non-VIP) are most targeted by threat actors via email? And, more importantly – which entities (VIP/non-VIP) are more valuable if they are successfully compromised?
There are two types of VIPs:
1. When referring to emails and phishing, VIPs are the users in an organization who are well known publicly.
2. When referring to attack paths, VIPs are users in an organization that are known publicly and have access to highly privileged assets.
Not every prominent user has access to critical assets, and not every user that has access to critical assets is prominent.
Darktrace analysis of VIP impersonation
We analyzed patterns of attack pathways and phishing attempts across 20 customer deployments from a large, randomized pool encompassing a diverse range of organizations.
Understanding Attack Pathways
Our observations revealed that 57% of low-difficulty attack paths originated from VIP entities, while 43% of observed low-difficulty attack paths towards critical assets or entities began through non-VIP users. This means that targeting VIPs is not the only way attackers can reach critical assets, and that non-VIP users must be considered as well.
While the sample size prevents us from establishing statistical significance across all customers, the randomized selection lends credence to the generalizability of these findings to other environments.
Phishing Attempts
On average, 1.35% of total emails sent to these customers exhibited significantly malicious properties associated with phishing or some form of impersonation. Strikingly, nearly half of these malicious emails (49.6%) were directed towards VIPs, while the rest were sent to non-VIPs. This near-equal split is worth noting, as attack paths show that non-VIPs also serve as potential entry points for targeting critical assets.
Figure 1: A phishing email actioned by Darktrace, sent to multiple VIP and non-VIP entities
For example, a recent phishing campaign targeted multiple customers across deployments, with five out of 13 emails specifically aimed at VIP users. Darktrace/Email actioned the malicious emails by double locking the links, holding the messages, and stripping the attachments.
Given that non-VIP users receive nearly half of the phishing or impersonation emails, it underscores the critical importance for security teams to recognize their blind spots in protecting critical assets. Overlooking the potential threat originating from non-VIP entities could lead to severe consequences. For instance, if a non-VIP user falls victim to a phishing attack or gets compromised, their credentials could be exploited to move laterally within the organization, potentially reaching critical assets.
This highlights the necessity for a sophisticated security tool that can identify targeted users, without the need for extensive customization and regardless of VIP status. By deploying a solution capable of promptly responding to email threats – including solicitation, phishing attempts, and impersonation – regardless of the status of the targeted user, security teams can significantly enhance their defense postures.
Darktrace vs Traditional Email Detection Methods
Traditional rules and signatures-based detection mechanisms fall short in identifying the evolving threats we’ve observed, due to their reliance on knowledge of past attacks to categorize emails.
Secure Email Gateway (SEG) or Integrated Cloud Email Security (ICES) tools categorize emails based on previous or known attacks, operating on a known-good or known-bad model. Even if tools use AI to automate this process, the approach is still fundamentally looking to the past and therefore vulnerable to unknown and zero-day threats.
Darktrace uses AI to understand each unique organization and how its email environment interoperates with each user and device on the network. Consequently, it is able to identify the subtle deviations from normal behavior that qualify as suspicious. This approach goes beyond simplistic categorizations, considering factors such as the sender’s history and recipient’s exposure score.
This nuanced analysis enables Darktrace to differentiate between genuine communications and malicious impersonation attempts. It automatically understands who is a VIP, without the need for manual input, and will action more strongly on incoming malicious emails based on a user’s status.
Email does determine who is a VIP, without a need of manual input, and will action more strongly on incoming malicious emails.
Darktrace/Email also feeds into Darktrace’s preventative security tools, giving the interconnected AI engines further context for assessing the high-value targets and pathways to vital internal systems and assets that start via the inbox.
Leveraging AI for Enhanced Protection Across the Enterprise
The efficacy of AI-driven security solutions lies in their ability to make informed decisions and recommendations based on real-time business data. By leveraging this data, AI driven solutions can identify exploitable attack pathways and an organizations most critical assets. Darktrace uniquely uses several forms of AI to equip security teams with the insights needed to make informed decisions about which pathways to secure, reducing human bias around the importance of protecting VIPs.
With the emergence of tools like AutoGPT, identifying potential targets for phishing attacks has become increasingly simplified. However, the real challenge lies in gaining a comprehensive understanding of all possible and low-difficulty attack paths leading to critical assets and identities within the organization.
At the same time, organizations need email tools that can leverage the understanding of users to prevent email threats from succeeding in the first instance. For every email and user, Darktrace/Email takes into consideration changes in behavior from the sender, recipient, content, and language, and many other factors.
Integrating Darktrace/Email with Darktrace’s attack path modeling capabilities enables comprehensive threat contextualization and facilitates a deeper understanding of attack pathways. This holistic approach ensures that all potential vulnerabilities, irrespective of the user's status, are addressed, strengthening the overall security posture.
Conclusion
Contrary to conventional wisdom, our analysis suggests that the distinction between VIPs and non-VIPs in terms of susceptibility to impersonation and low-difficulty attack paths is not as pronounced as presumed. Therefore, security teams must adopt a proactive stance in safeguarding all pathways, rather than solely focusing on VIPs.
Attack path modeling enhances Darktrace/Email's capabilities by providing crucial metrics on potential impact, damage, exposure, and weakness, enabling more targeted and effective threat mitigation strategies. For example, stronger email actions can be enforced for users who are known to have a high potential impact in case of compromise.
In an era where cyber threats continue to evolve in complexity, an adaptive and non-siloed approach to securing inboxes, high-priority individuals, and critical assets is indispensable.
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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.
Author
Kendra Gonzalez Duran
Director, Field CISO
Kendra Gonzalez Duran is Director, Field CISO at Darktrace, a leading AI company for cyber defense. At Darktrace, Kendra works with leading organizations in a range of industries to deploy and operationalize cutting edge technologies. During Kendra’s tenure at Darktrace, the company has grown to over 4500 customers and has been the recipient of numerous achievements, including The Golden Bridge Awards – Company of the year and Fortress Cybersecurity Award for Antigena Email. Kendra holds a Bachelor’s degree from University of California, Berkeley and is based in Darktrace’s Los Angeles office.
Darktrace's Detection of State-Linked ShadowPad Malware
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.
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.
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.
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.
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
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.
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.
Figure 6: Screenshotof 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.
Figure 7: Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]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
Figure 9: Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.
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
Survey findings: AI Cyber Threats are a Reality, the People are Acting Now
Artificial intelligence is changing the cybersecurity field as fast as any other, both on the offensive and defensive side. We surveyed over 1,500 cybersecurity professionals from around the world to uncover their attitudes, understanding, and priorities when it comes to AI cybersecurity in 2025. Our full report, unearthing some telling trends, is out now.
Nearly 74% of participants say AI-powered threats are a major challenge for their organization and 90% expect these threats to have a significant impact over the next one to two years, a slight increase from last year. These statistics highlight that AI is not just an emerging risk but a present and evolving one.
As attackers harness AI to automate and scale their operations, security teams must adapt just as quickly. Organizations that fail to prioritize AI-specific security measures risk falling behind, making proactive defense strategies more critical than ever.
Some of the most pressing AI-driven cyber threats include:
AI-powered social engineering: Attackers are leveraging AI to craft highly personalized and convincing phishing emails, making them harder to detect and more likely to bypass traditional defenses.
More advanced attacks at speed and scale: AI lowers the barrier for less skilled threat actors, allowing them to launch sophisticated attacks with minimal effort.
Attacks targeting AI systems: Cybercriminals are increasingly going after AI itself, compromising machine learning models, tampering with training data, and exploiting vulnerabilities in AI-driven applications and APIs.
Safe and secure use of AI
AI is having an effect on the cyber-threat landscape, but it also is starting to impact every aspect of a business – from marketing to HR to operations. The accessibility of AI tools for employees improves workflows, but also poses risks like data privacy violations, shadow AI, and violation of industry regulations.
How are security practitioners accommodating for this uptick in AI use across business?
Among survey participants 45% of security practitioners say they had already established a policy on the safe and secure use of AI and around 50% are in discussions to do so.
While almost all participants acknowledge that this is a topic that needs to be addressed, the gap between discussion and execution could underscore a need for greater insight, stronger leadership commitment, and adaptable security frameworks to keep pace with AI advancements in the workplace. The most popular actions taken are:
Implemented security controls to prevent unwanted exposure of corporate data when using AI technology (67%)
Implemented security controls to protect against other threats/risks associated with using AI technology (62%)
This year specifically, we see further action being taken with the implementation of security controls, training, and oversight.
For a more detailed breakdown that includes results based on industry and organizational size, download the full report here.
AI threats are rising, but security teams still face major challenges
78% of CISOs say AI-powered cyber-threats are already having a significant impact on their organization, a 5% increase from last year.
While cyber professionals feel more prepared for AI powered threats than they did 12 months ago, 45% still say their organization is not adequately prepared—down from 60% last year.
Despite this optimism, key challenges remain, including:
A shortage of personnel to manage tools and alerts
Gaps in knowledge and skills related to AI-driven countermeasures
Confidence in traditional security tools vs. new AI based tools
This year, 73% of survey participants expressed confidence in their security team’s proficiency in using AI within their tool stack, marking an increase from the previous year.
However, only 50% of participants have confidence in traditional cybersecurity tools to detect and block AI-powered threats. In contrast, 75% of participants are confident in AI-powered security solutions for detecting and blocking such threats and attacks.
As leading organizations continue to implement and optimize their use of AI, they are incorporating it into an increasing number of workflows. This growing familiarity with AI is likely to boost the confidence levels of practitioners even further.
The data indicates a clear trend towards greater reliance on AI-powered security solutions over traditional tools. As organizations become more adept at integrating AI into their operations, their confidence in these advanced technologies grows.
This shift underscores the importance of staying current with AI advancements and ensuring that security teams are well-trained in utilizing these tools effectively. The increasing confidence in AI-driven solutions reflects their potential to enhance cybersecurity measures and better protect against sophisticated threats.
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.
![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.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dbda2020b168dc1d83c2_Screenshot%202025-03-12%20at%2012.07.41%E2%80%AFPM.png)
![Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dd09fe9cf54a67c48f13_Screenshot%202025-03-12%20at%2012.14.04%E2%80%AFPM.png)
![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](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dd45f3743ebe06d81d89_Screenshot%202025-03-12%20at%2012.14.46%E2%80%AFPM.png)
