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April 10, 2023

Employee-Conscious Email Security Solutions in the Workforce

Email threats commonly affect organizations. Read Darktrace's expert insights on how to safeguard your business by educating employees about email security.
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
Dan Fein
VP, Product
Written by
Carlos Gray
Senior Product Marketing Manager, Email
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10
Apr 2023

When considering email security, IT teams have historically had to choose between excluding employees entirely, or including them but giving them too much power and implementing unenforceable, trust-based policies that try to make up for it. 

However, just because email security should not rely on employees, this does not mean they should be excluded entirely. Employees are the ones interacting with emails daily, and their experiences and behaviors can provide valuable security insights and even influence productivity. 

AI technology supports employee engagement in this non-intrusive, nuanced way to not only maintain email security, but also enhance it. 

Finding a Balance of Employee Involvement in Security Strategies

Historically, security solutions offered ‘all or nothing’ approaches to employee engagement. On one hand, when employees are involved, they are unreliable. Employees cannot all be experts in security on top of their actual job responsibilities, and mistakes are bound to happen in fast-paced environments.  

Although there have been attempts to raise security awareness, they often have shortcomings, as training emails lack context and realism, leaving employees with poor understandings that often lead to reporting emails that are actually safe. Having users constantly triaging their inboxes and reporting safe emails wastes time that takes away from their own productivity as well as the productivity of the security team.

Other historic forms of employee involvement also put security at risk. For example, users could create blanket rules through feedback, which could lead to common problems like safe-listing every email that comes from the gmail.com domain. Other times, employees could choose for themselves to release emails without context or limitations, introducing major risks to the organization. While these types of actions include employees to participate in security, they do so at the cost of security. 

Even lower stakes employee involvement can prove ineffective. For example, excessive warnings when sending emails to external contacts can lead to banner fatigue. When employees see the same warning message or alert at the top of every message, it’s human nature that they soon become accustomed and ultimately immune to it.

On the other hand, when employees are fully excluded from security, an opportunity is missed to fine-tune security according to the actual users and to gain feedback on how well the email security solution is working. 

So, both options of historically conventional email security, to include or exclude employees, prove incapable of leveraging employees effectively. The best email security practice strikes a balance between these two extremes, allowing more nuanced interactions that maintain security without interrupting daily business operations. This can be achieved with AI that tailors the interactions specifically to each employee to add to security instead of detracting from it. 

Reducing False Reports While Improving Security Awareness Training 

Humans and AI-powered email security can simultaneously level up by working together. AI can inform employees and employees can inform AI in an employee-AI feedback loop.  

By understanding ‘normal’ behavior for every email user, AI can identify unusual, risky components of an email and take precise action based on the nature of the email to neutralize them, such as rewriting links, flattening attachments, and moving emails to junk. AI can go one step further and explain in non-technical language why it has taken a specific action, which educates users. In contrast to point-in-time simulated phishing email campaigns, this means AI can share its analysis in context and in real time at the moment a user is questioning an email. 

The employee-AI feedback loop educates employees so that they can serve as additional enrichment data. It determines the appropriate levels to inform and teach users, while not relying on them for threat detection

In the other direction, the AI learns from users’ activity in the inbox and gradually factors this into its decision-making. This is not a ‘one size fits all’ mechanism – one employee marking an email as safe will never result in blanket approval across the business – but over time, patterns can be observed and autonomous decision-making enhanced.  

Figure 1: The employee-AI feedback loop increases employee understanding without putting security at risk.

The employee-AI feedback loop draws out the maximum potential benefits of employee involvement in email security. Other email security solutions only consider the security team, enhancing its workflow but never considering the employees that report suspicious emails. Employees who try to do the right thing but blindly report emails never learn or improve and end up wasting their own time. By considering employees and improving security awareness training, the employee-AI feedback loop can level up users. They learn from the AI explanations how to identify malicious components, and so then report fewer emails but with greater accuracy. 

While AI programs have classically acted like black boxes, Darktrace trains its AI on the best data, the organization’s actual employees, and invites both the security team and employees to see the reasoning behind its conclusions. Over time, employees will trust themselves more as they better learn how to discern unsafe emails. 

Leveraging AI to Generate Productivity Gains

Uniquely, AI-powered email security can have effects outside of security-related areas. It can save time by managing non-productive email. As the AI constantly learns employee behavior in the inbox, it becomes extremely effective at detecting spam and graymail – emails that aren't necessarily malicious, but clutter inboxes and hamper productivity. It does this on a per-user basis, specific to how each employee treats spam, graymail, and newsletters. The AI learns to detect this clutter and eventually learns which to pull from the inbox, saving time for the employees. This highlights how security solutions can go even further than merely protecting the email environment with a light touch, to the point where AI can promote productivity gains by automating tasks like inbox sorting.

Preventing Email Mishaps: How to Deal with Human Error

Improved user understanding and decision making cannot stop natural human error. Employees are bound to make mistakes and can easily send emails to the wrong people, especially when Outlook auto-fills the wrong recipient. This can have effects ranging anywhere from embarrassing to critical, with major implications on compliance, customer trust, confidential intellectual property, and data loss. 

However, AI can help reduce instances of accidentally sending emails to the wrong people. When a user goes to send an email in Outlook, the AI will analyze the recipients. It considers the contextual relationship between the sender and recipients, the relationships the recipients have with each other, how similar each recipient’s name and history is to other known contacts, and the names of attached files.  

If the AI determines that the email is outside of a user’s typical behavior, it may alert the user. Security teams can customize what the AI does next: it can block the email, block the email but allow the user to override it, or do nothing but invite the user to think twice. Since the AI analyzes each email, these alerts are more effective than consistent, blanket alerts warning about external recipients, which often go ignored. With this targeted approach, the AI prevents data leakage and reduces cyber risk. 

Since the AI is always on and continuously learning, it can adapt autonomously to employee changes. If the role of an employee evolves, the AI will learn the new normal, including common behaviors, recipients, attached file names, and more. This allows the AI to continue effectively flagging potential instances of human error, without needing manual rule changes or disrupting the employee’s workflow. 

Email Security Informed by Employee Experience

As the practical users of email, employees should be considered when designing email security. This employee-conscious lens to security can strengthen defenses, improve productivity, and prevent data loss.  

In these ways, email security can benefit both employees and security teams. Employees can become another layer of defense with improved security awareness training that cuts down on false reports of safe emails. This insight into employee email behavior can also enhance employee productivity by learning and sorting graymail. Finally, viewing security in relation to employees can help security teams deploy tools that reduce data loss by flagging misdirected emails. With these capabilities, Darktrace/Email™ enables security teams to optimize the balance of employee involvement in email security.

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
Dan Fein
VP, Product
Written by
Carlos Gray
Senior Product Marketing Manager, Email

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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 19, 2025

Customer Case Study: Leading Petrochemical Manufacturer

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Headquartered in Saudi Arabia, this industry leading petrochemical manufacturer serves customers in more than 80 countries across diverse markets throughout Europe, Africa, Latin America, the Middle East, China, and Southeast Asia.

Cyber resiliency critical to growth strategy

This leading petrochemical manufacturer’s vision is to be one of the major global players in the production and marketing of designated petrochemicals and downstream products. The company aims to significantly increase its capacity to up to a million metric tons within the next few years.

With cyber-attacks on critical infrastructure increasing 30% globally last year, cyber resiliency is essential to supporting the company’s strategic business goals of:

  • Maximizing production through efficient asset utilization
  • Maximizing sales by conducting 90% of its business outside Saudi Arabia
  • Optimizing resources and processes by integrating with UN Global Compact principles for sustainability and efficiency
  • Growing its business portfolio by engaging in joint ventures to diversify production and add value to the economy

However, the industry leader faced several challenges in its drive to fortify its cybersecurity defenses.

Visibility gaps delay response time

The company’s existing security setup provided limited visibility to the in-house security team, hindering its ability to detect anomalous network and user activity in real time. This resulted in delayed responses to potential incidents, making proactive issue resolution difficult and any remediation in the event of a successful attack costly and time-consuming.

Manual detection drains resources

Without automated detection and response capabilities, the organization’s security team had to manually monitor for suspicious activity – a time-consuming and inefficient approach that strained resources and left the organization vulnerable. This made it difficult for the team to stay current with training or acquire new skills and certifications, which are core to the ethos of both the company’s owners and the team itself.

Cyber-attacks on critical infrastructure increasing

The petrochemical manufacturer is part of a broader ecosystem of companies, making the protection of its supply chain – both upstream and downstream – critical. With several manufacturing entities and multiple locations, the customer’s internal structure is complex and challenging to secure. As cyber-attacks on critical infrastructure escalate, it needed a more comprehensive approach to safeguard its business and the wider ecosystem.

Keeping and growing skills and focus in-house

To strengthen its cybersecurity strategy, the company considered two options:

  1. Make a significant initial and ongoing investment in a Security Operations Center (SOC), which would involve skills development outside the company and substantial management overhead.
  2. Use a combination of new, automated tools and an outsourced Managed Detection and Response (MDR) service to reduce the burden on internal security specialists and allow the company to invest in upskilling its staff so they can focus on more strategic tasks.

Faced with this choice between entirely outsourcing security and augmenting the security team with new capabilities, the customer chose the second option, selecting Darktrace to automate the company’s monitoring, detection, and response. Today, the petrochemical manufacturer is using:

Extending the SOC with 24/7 expert support

To alleviate the burden on its lean security team, the company augmented its in-house capabilities with Darktrace’s Managed Detection & Response service. This support acts as an extension of its SOC, providing 24/7 monitoring, investigation, and escalation of high-priority threats. With Darktrace’s global SOC managing alert triage and autonomously containing threats, the organization’s internal team can focus on strategic initiatives. The result is a stronger security posture and increased capacity to proactively address evolving cyber risks – without expanding headcount or sacrificing visibility.

A unique approach to AI

In its search for a new security platform, the company’s Director of Information Technology said Darktrace’s autonomous response capability, coupled with Self-Learning AI-driven threat reduction, were two big reasons for selecting Darktrace over competing products and services.

AI was a huge factor – no one else was doing what Darktrace was doing with [AI].”

Demonstrated visibility

Before Darktrace, the customer had no visibility into the network activity to and from remote worker devices. Some employees need the ability to connect to its networks at any time and from any location, including the Director of Information Technology. The trial deployment of Darktrace / ENDPOINT was a success and gave the team peace of mind that, no matter the location or device, high-value remote workers were protected by Darktrace.

Modular architecture  

Darktrace's modular architecture allowed the company to deploy security controls across its complex, multi-entity environment. The company’s different locations run on segregated networks but are still interconnected and need to be protected. Darktrace / NETWORK provides a unified view and coordinated security response across the organization’s entire network infrastructure, including endpoint devices.

Results

The petrochemical manufacturer is using Darktrace across all of its locations and has achieved total visibility across network and user activity. “Darktrace is increasing in value every day,” said the Director of Information Technology.

I don’t have a big team, and Darktrace makes our lives very, very easy, not least the automation of some of the tasks that require constant manual review.”

Time savings frees analysts to focus on proactive security

Darktrace / NETWORK provides continuous, AI-driven monitoring and analysis of the company’s network activity, user behavior, and threat patterns, establishing a baseline of what normal activity looks like, and then alerting analysts to any deviations from normal traffic, activity, and behaviors. Darktrace’s autonomous response capabilities speed up response to detected threats, meaning intervention from the security team is required for fewer incidents and alerts.

In October 2024 alone, Darktrace Cyber AI Analyst saved the team 810 investigation hours, and autonomously responded to 180 anomalous behaviors that were uncovered during the investigations. With Darktrace managing the majority of threat detection and response efforts, the security team has been able to change its day-to-day activity from manual review of traffic and alerts and belated response to activity, to proactively fortifying its detection and response posture and upskilling to meet evolving requirements.  

Layered email protection reduces phishing threats

The company’s email infrastructure posed a challenge due to petrochemical industry regulations requiring on-premises email servers, with some security delivered via Microsoft Azure. By integrating Darktrace / EMAIL into the Azure stack, the organization has reduced the volume of phishing emails its users receive by 5%.

“Now we have one more layer of security related to email – every email goes through two filters. If something is not being caught or traced by Azure, it is being detected by Darktrace,” said the Director of Information Technology. “As a result, we’re now seeing only about 15% to 20% of the phishing emails we used to receive before implementing Darktrace.”

Preparing for a secure future

The time saved using Darktrace has helped the security team take proactive steps, including preparing for new cyber resilience regulations for Saudi Arabia’s Critical National Infrastructure, as mandated by the National Cybersecurity Authority (NCA).

“The team now has ample time to prepare policies and procedures that meet the new NCA regulations and, in some cases, enhance the requirements of the new law,” said the Director of Information Technology. “All of this is possible because they don’t need to keep watch; Darktrace takes on so much of that task for them.”

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