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February 22, 2024

Attack Trends: VIP Impersonation in the Business Hierarchy

VIP Impersonation occurs when a cyber-threat actor impersonates a prominent employee to obtain sensitive data. Learn all about VIP impersonation here.
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.
Written by
Kendra Gonzalez Duran
Principal Analyst
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22
Feb 2024

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.  

Darktrace/Email UI
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.  

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.
Written by
Kendra Gonzalez Duran
Principal Analyst

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June 27, 2025

Patch and Persist: Darktrace’s Detection of Blind Eagle (APT-C-36)

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What is Blind Eagle?

Since 2018, APT-C-36, also known as Blind Eagle, has been observed performing cyber-attacks targeting various sectors across multiple countries in Latin America, with a particular focus on Colombian organizations.

Blind Eagle characteristically targets government institutions, financial organizations, and critical infrastructure [1][2].

Attacks carried out by Blind Eagle actors typically start with a phishing email and the group have been observed utilizing various Remote Access Trojans (RAT) variants, which often have in-built methods for hiding command-and-control (C2) traffic from detection [3].

What we know about Blind Eagle from a recent campaign

Since November 2024, Blind Eagle actors have been conducting an ongoing campaign targeting Colombian organizations [1].

In this campaign, threat actors have been observed using phishing emails to deliver malicious URL links to targeted recipients, similar to the way threat actors have previously been observed exploiting CVE-2024-43451, a vulnerability in Microsoft Windows that allows the disclosure of a user’s NTLMv2 password hash upon minimal interaction with a malicious file [4].

Despite Microsoft patching this vulnerability in November 2024 [1][4], Blind Eagle actors have continued to exploit the minimal interaction mechanism, though no longer with the intent of harvesting NTLMv2 password hashes. Instead, phishing emails are sent to targets containing a malicious URL which, when clicked, initiates the download of a malicious file. This file is then triggered by minimal user interaction.

Clicking on the file triggers a WebDAV request, with a connection being made over HTTP port 80 using the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19044’. WebDAV is a transmission protocol which allows files or complete directories to be made available through the internet, and to be transmitted to devices [5]. The next stage payload is then downloaded via another WebDAV request and malware is executed on the target device.

Attackers are notified when a recipient downloads the malicious files they send, providing an insight into potential targets [1].

Darktrace’s coverage of Blind Eagle

In late February 2025, Darktrace observed activity assessed with medium confidence to be  associated with Blind Eagle on the network of a customer in Colombia.

Within a period of just five hours, Darktrace / NETWORK detected a device being redirected through a rare external location, downloading multiple executable files, and ultimately exfiltrating data from the customer’s environment.

Since the customer did not have Darktrace’s Autonomous Response capability enabled on their network, no actions were taken to contain the compromise, allowing it to escalate until the customer’s security team responded to the alerts provided by Darktrace.

Darktrace observed a device on the customer’s network being directed over HTTP to a rare external IP, namely 62[.]60[.]226[.]112, which had never previously been seen in this customer’s environment and was geolocated in Germany. Multiple open-source intelligence (OSINT) providers have since linked this endpoint with phishing and malware campaigns [9].

The device then proceeded to download the executable file hxxp://62[.]60[.]226[.]112/file/3601_2042.exe.

Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
Figure 1: Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
Darktrace’s detection of the affected device downloading an executable file from the suspicious endpoint.
Figure 2: Darktrace’s detection of the affected device downloading an executable file from the suspicious endpoint.

The device was then observed making unusual connections to the rare endpoint 21ene.ip-ddns[.]com and performing unusual external data activity.

This dynamic DNS endpoint allows a device to access an endpoint using a domain name in place of a changing IP address. Dynamic DNS services ensure the DNS record of a domain name is automatically updated when the IP address changes. As such, malicious actors can use these services and endpoints to dynamically establish connections to C2 infrastructure [6].

Further investigation into this dynamic endpoint using OSINT revealed multiple associations with previous likely Blind Eagle compromises, as well as Remcos malware, a RAT commonly deployed via phishing campaigns [7][8][10].

Darktrace’s detection of the affected device connecting to the suspicious dynamic DNS endpoint, 21ene.ip-ddns[.]com.
Figure 3: Darktrace’s detection of the affected device connecting to the suspicious dynamic DNS endpoint, 21ene.ip-ddns[.]com.

Shortly after this, Darktrace observed the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19045’, indicating usage of the aforementioned transmission protocol WebDAV. The device was subsequently observed connected to an endpoint associated with Github and downloading data, suggesting that the device was retrieving a malicious tool or payload. The device then began to communicate to the malicious endpoint diciembrenotasenclub[.]longmusic[.]com over the new TCP port 1512 [11].

Around this time, the device was also observed uploading data to the endpoints 21ene.ip-ddns[.]com and diciembrenotasenclub[.]longmusic[.]com, with transfers of 60 MiB and 5.6 MiB observed respectively.

Figure 4: UI graph showing external data transfer activity.

This chain of activity triggered an Enhanced Monitoring model alert in Darktrace / NETWORK. These high-priority model alerts are designed to trigger in response to higher fidelity indicators of compromise (IoCs), suggesting that a device is performing activity consistent with a compromise.

 Darktrace’s detection of initial attack chain activity.
Figure 5: Darktrace’s detection of initial attack chain activity.

A second Enhanced Monitoring model was also triggered by this device following the download of the aforementioned executable file (hxxp://62[.]60[.]226[.]112/file/3601_2042.exe) and the observed increase in C2 activity.

Following this activity, Darktrace continued to observe the device beaconing to the 21ene.ip-ddns[.]com endpoint.

Darktrace’s Cyber AI Analyst was able to correlate each of the individual detections involved in this compromise, identifying them as part of a broader incident that encompassed C2 connectivity, suspicious downloads, and external data transfers.

Cyber AI Analyst’s investigation into the activity observed on the affected device.
Figure 6: Cyber AI Analyst’s investigation into the activity observed on the affected device.
Figure 7: Cyber AI Analyst’s detection of the affected device’s broader connectivity throughout the course of the attack.

As the affected customer did not have Darktrace’s Autonomous Response configured at the time, the attack was able to progress unabated. Had Darktrace been properly enabled, it would have been able to take a number of actions to halt the escalation of the attack.

For example, the unusual beaconing connections and the download of an unexpected file from an uncommon location would have been shut down by blocking the device from making external connections to the relevant destinations.

Conclusion

The persistence of Blind Eagle and ability to adapt its tactics, even after patches were released, and the speed at which the group were able to continue using pre-established TTPs highlights that timely vulnerability management and patch application, while essential, is not a standalone defense.

Organizations must adopt security solutions that use anomaly-based detection to identify emerging and adapting threats by recognizing deviations in user or device behavior that may indicate malicious activity. Complementing this with an autonomous decision maker that can identify, connect, and contain compromise-like activity is crucial for safeguarding organizational networks against constantly evolving and sophisticated threat actors.

Credit to Charlotte Thompson (Senior Cyber Analyst), Eugene Chua (Principal Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Appendices

IoCs

IoC – Type - Confidence
Microsoft-WebDAV-MiniRedir/10.0.19045 – User Agent

62[.]60[.]226[.]112 – IP – Medium Confidence

hxxp://62[.]60[.]226[.]112/file/3601_2042.exe – Payload Download – Medium Confidence

21ene.ip-ddns[.]com – Dynamic DNS Endpoint – Medium Confidence

diciembrenotasenclub[.]longmusic[.]com  - Hostname – Medium Confidence

Darktrace’s model alert coverage

Anomalous File / Suspicious HTTP Redirect
Anomalous File / EXE from Rare External Location
Anomalous File / Multiple EXE from Rare External Location
Anomalous Server Activity / Outgoing from Server
Unusual Activity / Unusual External Data to New Endpoint
Device / Anomalous Github Download
Anomalous Connection / Multiple Connections to New External TCP Port
Device / Initial Attack Chain Activity
Anomalous Server Activity / Rare External from Server
Compromise / Suspicious File and C2
Compromise / Fast Beaconing to DGA
Compromise / Large Number of Suspicious Failed Connections
Device / Large Number of Model Alert

Mitre Attack Mapping:

Tactic – Technique – Technique Name

Initial Access - T1189 – Drive-by Compromise
Initial Access - T1190 – Exploit Public-Facing Application
Initial Access ICS - T0862 – Supply Chain Compromise
Initial Access ICS - T0865 – Spearphishing Attachment
Initial Access ICS - T0817 - Drive-by Compromise
Resource Development - T1588.001 – Malware
Lateral Movement ICS - T0843 – Program Download
Command and Control - T1105 - Ingress Tool Transfer
Command and Control - T1095 – Non-Application Layer Protocol
Command and Control - T1571 – Non-Standard Port
Command and Control - T1568.002 – Domain Generation Algorithms
Command and Control ICS - T0869 – Standard Application Layer Protocol
Evasion ICS - T0849 – Masquerading
Exfiltration - T1041 – Exfiltration Over C2 Channel
Exfiltration - T1567.002 – Exfiltration to Cloud Storage

References

1)    https://research.checkpoint.com/2025/blind-eagle-and-justice-for-all/

2)    https://assets.kpmg.com/content/dam/kpmgsites/in/pdf/2025/04/kpmg-ctip-blind-eagle-01-apr-2025.pdf.coredownload.inline.pdf

3)    https://www.checkpoint.com/cyber-hub/threat-prevention/what-is-remote-access-trojan/#:~:text=They%20might%20be%20attached%20to,remote%20access%20or%20system%20administration

4)    https://msrc.microsoft.com/update-guide/vulnerability/CVE-2024-43451

5)    https://www.ionos.co.uk/digitalguide/server/know-how/webdav/

6)    https://vercara.digicert.com/resources/dynamic-dns-resolution-as-an-obfuscation-technique

7)    https://threatfox.abuse.ch/ioc/1437795

8)    https://www.checkpoint.com/cyber-hub/threat-prevention/what-is-malware/remcos-malware/

9)    https://www.virustotal.com/gui/url/b3189db6ddc578005cb6986f86e9680e7f71fe69f87f9498fa77ed7b1285e268

10) https://www.virustotal.com/gui/domain/21ene.ip-ddns.com

11) https://www.virustotal.com/gui/domain/diciembrenotasenclub.longmusic.com/community

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About the author
Charlotte Thompson
Cyber Analyst

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June 18, 2025

Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision

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In today’s threat landscape, email remains the most targeted vector for cyberattacks. Organizations require not only multi-layered defenses but also advanced, integrated systems that work collaboratively to proactively mitigate threats before they cause damage

That’s why we’re proud to announce a new integration between Darktrace / EMAIL and Microsoft Defender for Office 365, delivering a Unified Quarantine experience that empowers security teams with seamless visibility, control, and response across both platforms.

This announcement builds on a strong and growing collaboration. In 2024, Darktrace was honored as Microsoft UK Partner of the Year and recognized as a Security Trailblazer at the annual Microsoft Security 20/20 Awards, a testament to our shared commitment to innovation and customer-centric security.

A Shared Mission: Stopping Threats at Machine Speed

This integration is more than a technical milestone,as it’s a reflection of a shared mission: to protect organizations from both known and unknown threats, with efficiency, accuracy, and transparency.

  • Microsoft Defender for Office 365 delivers a comprehensive security framework that safeguards Microsoft 365 email and collaboration workloads leveraging advanced AI, global threat intelligence and information on known attack infrastructure.
  • Darktrace / EMAIL complements this with Self-Learning AI that understands the unique communication patterns within each organization, detecting subtle anomalies that evade traditional detection methods.

Together, we’re delivering multi-layered, adaptive protection that’s greater than the sum of its parts.

“Our integration with Microsoft gives security teams the tools they need to act faster and more precisely to detect and respond to threats,” said Jill Popelka, CEO of Darktrace. “Together, we’re strengthening defenses where it matters most to our customers: at the inbox.”

Unified Quarantine: One View, Total Clarity

The new Unified Quarantine experience gives customers a single pane of glass to view and manage email threatsregardless of which product took action. This means:

  • Faster investigations with consolidated visibility
  • Clear attribution of actions and outcomes across both platforms
  • Streamlined workflows for security teams managing complex environments

“This integration is a testament to the power of combining Microsoft’s global threat intelligence with Darktrace’s unique ability to understand the ‘self’ of an organization,” said Jack Stockdale, CTO of Darktrace. “Together, we’re delivering a new standard in proactive, adaptive email security.”

A New Era of Collaborative Cyber Defense

This collaboration represents a broader shift in cybersecurity: from siloed tools to integrated ecosystems. As attackers become more sophisticated, defenders must move faster, smarter, and in unison.

Through this integration, Darktrace and Microsoft establish a new standard for collaboration between native and third-party security solutions, enhancing not only threat detection but also comprehensive understanding and proactive measures against threats.

We’re excited to bring this innovation to our customers and continue building a future where AI and human expertise collaborate to secure the enterprise.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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