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
George Kim
SOC Analyst
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23
Oct 2022
Two of the most popular ways threat actors send malicious emails is through the use of spoofing and impersonation tactics. While spoofed emails are sent on behalf of a trusted domain and obscure the true source of the sender, impersonation emails come from a fake domain, but one that may be visually confused for an authentic one. In order to identify impersonation tactics in a suspicious email, we should first ask why an attacker might utilize an impersonation approach over spoofing.
In contrast to domain spoofing, which lacks validation and can be readily detected by email security gateway softwares, impersonation with a lookalike domain allows attackers to send emails with full SPF and DKIM validation, making them appear legitimate to many security gateways. This blog will explore impersonation tactics and how Darktrace/Email protects against them.
There are two distinct ways to leverage impersonation tactics:
1. Impersonating the domain
2. Impersonating a real user from that domain
Domain impersonation is often implemented with the use of ‘confusable characters’. This involves misspelling through the use of character substitutions which make the domain look as visually similar to the original as possible (eg. m rn, o 0, l I). Threat actors can then also impersonate a real user by adding the the personal field of that user’s email to the new, malicious domain. Comparing impersonation emails with legitimate emails highlights how similar these malicious email addresses are to the real thing (Figure 1).
Figure 1- Email log that highlights the impersonated emails from “Mike Lewis” from the domain “smartercornmerce[.]net”. Along with the impersonated domain, the attackers attempt to impersonate the known user, “Mike Lewis” as well. The use of both distinct types of impersonation categorize the email as what Darktrace/Email refers to as a Double Impersonation email.
Figure 2- Email Summary details of one of the malicious double impersonation emails that was sent by the impersonated sender, “Mike Lewis” from “smartercornmerce[.]net”, that highlights the various anomaly indicators that Darktrace/Email detected, as well the various tags and actions it applied.
Darktrace/Email uses AI which analyses impersonation emails by comparing the ‘From’ header domains of emails against known external domains and generates a percentage score for how likely the domain is to be an imitation of the known domain (Figure 3).
Figure 3- Darktrace compares the external sender, “mike.lewis@smartercornmerce[.]net”, with similar external names and domains that have been observed in different inbound emails on the network.
Impersonation emails are also detected via spoof score metrics such as Domain External Spoof Score and Domain Internal Spoof Score (Figure 4).
Figure 4- Darktrace AI analyzed the malicious double impersonation email from Figure 2 and generated a high Domain External Spoof Score (100) and Spoof Score External (94)
Double Impersonation emails such as the one highlighted in Figure 2 are utilized by threat actors to gain the trust of the recipient and convince them to access malicious payloads such as phishing links and attachments. For example, the malicious double impersonation email from Figure 2 contained a suspicious hidden link to a Wordpress site which could have redirected the user to a phishing endpoint and tricked them into divulging sensitive information (Figure 5). The endpoint itself appears to lead unsuspecting recipients to a false share link posing as a payment-themed Excel file.
Figure 5- Details of the Wordpress link embedded in the suspicious email, which was hidden beneath display text to convince a user to click it without knowledge of where it would lead. The domain has a 100% rarity according to Darktrace AI.
Figure 6- Wordpress webpage that highlights another link for the user to click in order to be redirected to the invoice statement in a Microsoft Excel document.
Various indicators highlighted the webpage as suspicious and potentially malicious. Firstly, the use of ‘SmarterCORNmerce’ in the link to the webpage was at odds with the use of SmarterCOMMERCE throughout the page itself. The link also showed the invoice statement to be an Microsoft Excel file, despite the email suggesting it was a PDF document. Further investigation revealed the link to be associated with a Fleek hosting service and CDN (Figure 7), and that it redirected users to a fake Microsoft page.
Figure 7 - Source code from the Wordpress webpage shows that the fake Microsoft link redirects users to a Fleek hosted page. This page may contain additional javascript content to download malware onto the user’s device.
As well as the domain spoof score metrics highlighted in Figure 4, Darktrace/Email analyses the suspicious payloads embedded in emails and generates scores to indicate the likelihood that a payload may be a phishing attempt.
Figure 8- Additional metrics for the double impersonation email that highlight the high phishing inducement score (96) for the email.
As the DETECT functionality of Darktrace/Email generates high scores metrics such as Domain External Spoof Score and Phishing Inducement, the RESPOND function will fire complementary models which then trigger relevant actions on the various payloads embedded in these emails and even the delivery of the emails themselves. As the impersonation email highlighted in Figure 2 impersonated not only the trusted domain but the known and trusted sender, Darktrace AI triggers the Double Impersonation model. Additional spoofing models such as ‘Basic Known Entity Similarities + Suspicious Content’ and ‘External Domain Similarities + Maximum Similarity’ were also triggered, indicating the high possibility that the suspicious email is a domain and user impersonation email sent by a malicious attacker.
Figure 9- The Email console highlights the different models the email triggered, including the Basic Known Entity Similarities + Suspicious Content and External Domain Similarities + Maximum Similarity model breaches and the various models that triggered significant actions in response to the potentially malicious impersonation email.
When Darktrace/Email detects a malicious double impersonation email, it responds by triggering a Hold action, preventing the email from appearing in the recipient’s inbox. Darktrace/Email’s RESPOND functionality could also take action against the suspicious link payloads embedded in the email with a Double Lock Link action. This will prevent users from attempting to click on malicious phishing links. Such actions highlight how Darktrace/Email excels in using AI to detect and take action against potentially malicious impersonation emails that may be prevalent in any user’s inbox.
Though impersonation is becoming increasingly targeted and efficient, Darktrace/Email has both detection and response capabilities that can ensure customers have secure coverage for their email environments.
Thanks to Ben Atkins for his contributions to this blog.
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.
Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision
Darktrace and Microsoft have joined forces to enhance email security through a new integration, unifying threat response and quarantine capabilities. This collaboration strengthens defenses and streamlines visibility for security teams, reflecting a shared vision for proactive cyber protection.
Why attack-centric approaches to email security can’t cope with modern threats
Despite evolving email threats, many organizations still rely on SEGs or outdated, attack-focused methods. These approaches can’t counter advanced, AI-driven attacks. The solution? Business-centric email security that understands users and inbox behavior, not just threats.
Evaluating Email Security: How to Select the Best Solution for Your Organization
In today’s saturated market for email security, it can be difficult to cut through the noise of AI hype and vendor claims. CISOs should be using a structured evaluation framework to support informed, objective comparisons of different vendors – to allow them to make the best decision for their organization.
Patch and Persist: Darktrace’s Detection of Blind Eagle (APT-C-36)
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.
Figure 1: Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
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].
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.
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.
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
Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision
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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