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September 30, 2024

Business Email Compromise (BEC) in the Age of AI

Generative AI tools have increased the risk of BEC, and traditional cybersecurity defenses struggle to stay ahead of the growing speed, scale, and sophistication of attacks. Only multilayered, defense-in-depth strategies can counter the AI-powered BEC threat.
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
Carlos Gray
Senior Product Marketing Manager, Email
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30
Sep 2024

As people continue to be the weak link in most organizations’ cybersecurity practices, the growing use of generative AI tools in cyber-attacks makes email, their primary communications channel, a more compelling target than ever. The risk associated with Business Email Compromise (BEC) in particular continues to rise as generative AI tools equip attackers to build and launch social engineering and phishing campaigns with greater speed, scale, and sophistication.

What is BEC?

BEC is defined in different ways, but generally refers to cyber-attacks in which attackers abuse email — and users’ trust — to trick employees into transferring funds or divulging sensitive company data.

Unlike generic phishing emails, most BEC attacks do not rely on “spray and pray” dissemination or on users’ clicking bogus links or downloading malicious attachments. Instead, modern BEC campaigns use a technique called “pretexting.”

What is pretexting?

Pretexting is a more specific form of phishing that describes an urgent but false situation — the pretext — that requires the transfer of funds or revelation of confidential data.  

This type of attack, and therefore BEC, is dominating the email threat landscape. As reported in Verizon’s 2024 Data Breach Investigation Report, recently there has been a “clear overtaking of pretexting as a more likely social action than phishing.” The data shows pretexting, “continues to be the leading cause of cybersecurity incidents (accounting for 73% of breaches)” and one of “the most successful ways of monetizing a breach.”

Pretexting and BEC work so well because they exploit humans’ natural inclination to trust the people and companies they know. AI compounds the risk by making it easier for attackers to mimic known entities and harder for security tools and teams – let alone unsuspecting recipients of routine emails – to tell the difference.

BEC attacks now incorporate AI

With the growing use of AI by threat actors, trends point to BEC gaining momentum as a threat vector and becoming harder to detect. By adding ingenuity, machine speed, and scale, generative AI tools like OpenAI’s ChatGPT give threat actors the ability to create more personalized, targeted, and convincing emails at scale.

In 2023, Darktrace researchers observed a 135% rise in ‘novel social engineering attacks’ across Darktrace / EMAIL customers, corresponding with the widespread adoption of ChatGPT.

Large Language Models (LLMs) like ChatGPT can draft believable messages that feel like emails that target recipients expect to receive. For example, generative AI tools can be used to send fake invoices from vendors known to be involved with well-publicized construction projects. These messages also prove harder to detect as AI automatically:

  • Avoids misspellings and grammatical errors
  • Creates multiple variations of email text  
  • Translates messages that read well in multiple languages
  • And accomplishes additional, more targeted tactics

AI creates a force multiplier that allows primitive mass-mail campaigns to evolve into sophisticated automated attacks. Instead of spending weeks studying the target to craft an effective email, cybercriminals might only spend an hour or two and achieve a better result.  

Challenges of detecting AI-powered BEC attacks

Rules-based detections miss unknown attacks

One major challenge comes from the fact that rules based on known attacks have no basis to deny new threats. While native email security tools defend against known attacks, many modern BEC attacks use entirely novel language and can omit payloads altogether. Instead, they rely on pure social engineering or bide their time until security tools recognize the new sender as a legitimate contact.  

Most defensive AI can’t keep pace with attacker innovation

Security tools might focus on the meaning of an email’s text in trying to recognize a BEC attack, but defenders still end up in a rules and signature rat race. Some newer Integrated Cloud Email Security (ICES) vendors attempt to use AI defensively to improve the flawed approach of only looking for exact matches. Employing data augmentation to identify similar-looking emails helps to a point but not enough to outpace novel attacks built with generative AI.

What tools can stop BEC?

A modern defense-in-depth strategy must use AI to counter the impact of AI in the hands of attackers. As found in our 2024 State of AI Cybersecurity Report, 96% of survey participants believe AI-driven security solutions are a must have for countering AI-powered threats.

However, not all AI tools are the same. Since BEC attacks continue to change, defensive AI-powered tools should focus less on learning what attacks look like, and more on learning normal behavior for the business. By understanding expected behavior on the company’s side, the security solution will be able to recognize anomalous and therefore suspicious activity, regardless of the word choice or payload type.  

To combat the speed and scale of new attacks, an AI-led BEC defense should spot novel threats.

Darktrace / EMAIL™ can do that.  

Self-Learning AI builds profiles for every email user, including their relationships, tone and sentiment, content, and link sharing patterns. Rich context helps in understanding how people communicate and identifying deviations from the normal routine to determine what does and does not belong in an individual’s inbox and outbox.  

Other email security vendors may claim to use behavioral AI and unsupervised machine learning in their products, but their AI are still pre-trained with historical data or signatures to recognize malicious activity, rather than demonstrating a true learning process. Darktrace’s Self Learning-AI truly learns from the organization in which it is installed, allowing it to detect unknown and novel vectors that other security tools are not yet trained on.

Because Darktrace understands the human behind email communications rather than knowledge of past attacks, Darktrace / EMAIL can stop the most sophisticated and evolving email security risks. It enhances your native email security by leveraging business-centric behavioral anomaly detection across inbound, outbound, and lateral messages in both email and Teams.

This unique approach quickly identifies sophisticated threats like BEC, ransomware, phishing, and supply chain attacks without duplicating existing capabilities or relying on traditional rules, signatures, and payload analysis.  

The power of Darktrace’s AI can be seen in its speed and adaptability: Darktrace / EMAIL blocks the most novel threats up to 13 days faster than traditional security tools.

Learn more about AI-led BEC threats, how these threats extend beyond the inbox, and how organizations can adopt defensive AI to outpace attacker innovation in the white paper “Beyond the Inbox: A Guide to Preventing Business Email Compromise.”

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
Carlos Gray
Senior Product Marketing Manager, Email

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June 5, 2025

Unpacking ClickFix: Darktrace’s detection of a prolific social engineering tactic

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What is ClickFix and how does it work?

Amid heightened security awareness, threat actors continue to seek stealthy methods to infiltrate target networks, often finding the human end user to be the most vulnerable and easily exploited entry point.

ClickFix baiting is an exploitation of the end user, making use of social engineering techniques masquerading as error messages or routine verification processes, that can result in malicious code execution.

Since March 2024, the simplicity of this technique has drawn attention from a range of threat actors, from individual cybercriminals to Advanced Persistent Threat (APT) groups such as APT28 and MuddyWater, linked to Russia and Iran respectively, introducing security threats on a broader scale [1]. ClickFix campaigns have been observed affecting organizations in across multiple industries, including healthcare, hospitality, automotive and government [2][3].

Actors carrying out these targeted attacks typically utilize similar techniques, tools and procedures (TTPs) to gain initial access. These include spear phishing attacks, drive-by compromises, or exploiting trust in familiar online platforms, such as GitHub, to deliver malicious payloads [2][3]. Often, a hidden link within an email or malvertisements on compromised legitimate websites redirect the end user to a malicious URL [4]. These take the form of ‘Fix It’ or fake CAPTCHA prompts [4].

From there, users are misled into believing they are completing a human verification step, registering a device, or fixing a non-existent issue such as a webpage display error. As a result, they are guided through a three-step process that ultimately enables the execution of malicious PowerShell commands:

  1. Open a Windows Run dialog box [press Windows Key + R]
  2. Automatically or manually copy and paste a malicious PowerShell command into the terminal [press CTRL+V]
  3. And run the prompt [press ‘Enter’] [2]

Once the malicious PowerShell command is executed, threat actors then establish command and control (C2) communication within the targeted environment before moving laterally through the network with the intent of obtaining and stealing sensitive data [4]. Malicious payloads associated with various malware families, such as XWorm, Lumma, and AsyncRAT, are often deployed [2][3].

Attack timeline of ClickFix cyber attack

Based on investigations conducted by Darktrace’s Threat Research team in early 2025, this blog highlights Darktrace’s capability to detect ClickFix baiting activity following initial access.

Darktrace’s coverage of a ClickFix attack chain

Darktrace identified multiple ClickFix attacks across customer environments in both Europe, the Middle East, and Africa (EMEA) and the United States. The following incident details a specific attack on a customer network that occurred on April 9, 2025.

Although the initial access phase of this specific attack occurred outside Darktrace’s visibility, other affected networks showed compromise beginning with phishing emails or fake CAPTCHA prompts that led users to execute malicious PowerShell commands.

Darktrace’s visibility into the compromise began when the threat actor initiated external communication with their C2 infrastructure, with Darktrace / NETWORK detecting the use of a new PowerShell user agent, indicating an attempt at remote code execution.

Darktrace / NETWORK's detection of a device making an HTTP connection with new PowerShell user agent, indicating PowerShell abuse for C2 communications.
Figure 1: Darktrace / NETWORK's detection of a device making an HTTP connection with new PowerShell user agent, indicating PowerShell abuse for C2 communications.

Download of Malicious Files for Lateral Movement

A few minutes later, the compromised device was observed downloading a numerically named file. Numeric files like this are often intentionally nondescript and associated with malware. In this case, the file name adhered to a specific pattern, matching the regular expression: /174(\d){7}/. Further investigation into the file revealed that it contained additional malicious code designed to further exploit remote services and gather device information.

Darktrace / NETWORK's detection of a numeric file, one minute after the new PowerShell User Agent alert.
Figure 2: Darktrace / NETWORK's detection of a numeric file, one minute after the new PowerShell User Agent alert.

The file contained a script that sent system information to a specified IP address using an HTTP POST request, which also processed the response. This process was verified through packet capture (PCAP) analysis conducted by the Darktrace Threat Research team.

By analyzing the body content of the HTTP GET request, it was observed that the command converts the current time to Unix epoch time format (i.e., 9 April 2025 13:26:40 GMT), resulting in an additional numeric file observed in the URI: /1744205200.

PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.
Figure 3: PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.

Across Darktrace’s investigations into other customers' affected by ClickFix campaigns, both internal information discovery events and further execution of malicious code were observed.

Data Exfiltration

By following the HTTP stream in the same PCAP, the Darktrace Threat Research Team assessed the activity as indicative of data exfiltration involving system and device information to the same command-and-control (C2) endpoint, , 193.36.38[.]237. This endpoint was flagged as malicious by multiple open-source intelligence (OSINT) vendors [5].

PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.
Figure 4: PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.

Further analysis of Darktrace’s Advanced Search logs showed that the attacker’s malicious code scanned for internal system information, which was then sent to a C2 server via an HTTP POST request, indicating data exfiltration

Advanced Search further highlights Darktrace's observation of the HTTP POST request, with the second numeric file representing data exfiltration.
Figure 5: Advanced Search further highlights Darktrace's observation of the HTTP POST request, with the second numeric file representing data exfiltration.

Actions on objectives

Around ten minutes after the initial C2 communications, the compromised device was observed connecting to an additional rare endpoint, 188.34.195[.]44. Further analysis of this endpoint confirmed its association with ClickFix campaigns, with several OSINT vendors linking it to previously reported attacks [6].

In the final HTTP POST request made by the device, Darktrace detected a file at the URI /init1234 in the connection logs to the malicious endpoint 188.34.195[.]44, likely depicting the successful completion of the attack’s objective, automated data egress to a ClickFix C2 server.

Darktrace / NETWORK grouped together the observed indicators of compromise (IoCs) on the compromised device and triggered an Enhanced Monitoring model alert, a high-priority detection model designed to identify activity indicative of the early stages of an attack. These models are monitored and triaged 24/7 by Darktrace’s Security Operations Center (SOC) as part of the Managed Threat Detection service, ensuring customers are promptly notified of malicious activity as soon as it emerges.

Darktrace correlated the separate malicious connections that pertained to a single campaign.
Figure 6: Darktrace correlated the separate malicious connections that pertained to a single campaign.

Darktrace Autonomous Response

In the incident outlined above, Darktrace was not configured in Autonomous Response mode. As a result, while actions to block specific connections were suggested, they had to be manually implemented by the customer’s security team. Due to the speed of the attack, this need for manual intervention allowed the threat to escalate without interruption.

However, in a different example, Autonomous Response was fully enabled, allowing Darktrace to immediately block connections to the malicious endpoint (138.199.156[.]22) just one second after the initial connection in which a numerically named file was downloaded [7].

Darktrace Autonomous Response blocked connections to a suspicious endpoint following the observation of the numeric file download.
Figure 7: Darktrace Autonomous Response blocked connections to a suspicious endpoint following the observation of the numeric file download.

This customer was also subscribed to our Managed Detection and Response service, Darktrace’s SOC extended a ‘Quarantine Device’ action that had already been autonomously applied in order to buy their security team additional time for remediation.

Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.
Figure 8: Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.

Conclusion

ClickFix baiting is a widely used tactic in which threat actors exploit human error to bypass security defenses. By tricking end point users into performing seemingly harmless, everyday actions, attackers gain initial access to systems where they can access and exfiltrate sensitive data.

Darktrace’s anomaly-based approach to threat detection identifies early indicators of targeted attacks without relying on prior knowledge or IoCs. By continuously learning each device’s unique pattern of life, Darktrace detects subtle deviations that may signal a compromise. In this case, Darktrace's Autonomous Response, when operating in a fully autonomous mode, was able to swiftly contain the threat before it could progress further along the attack lifecycle.

Credit to Keanna Grelicha (Cyber Analyst) and Jennifer Beckett (Cyber Analyst)

Appendices

NETWORK Models

  • Device / New PowerShell User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Connection / Posting HTTP to IP Without Hostname
  • Anomalous Connection / Powershell to Rare External
  • Device / Suspicious Domain
  • Device / New User Agent and New IP
  • Anomalous File / New User Agent Followed By Numeric File Download (Enhanced Monitoring Model)
  • Device / Initial Attack Chain Activity (Enhanced Monitoring Model)

Autonomous Response Models

  • Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block
  • Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block
  • Antigena / Network::External Threat::Antigena File then New Outbound Block
  • Antigena / Network::External Threat::Antigena Suspicious File Block
  • Antigena / Network::Significant Anomaly::Antigena Alerts Over Time Block
  • Antigena / Network::External Threat::Antigena Suspicious File Block

IoC - Type - Description + Confidence

·       141.193.213[.]11 – IP address – Possible C2 Infrastructure

·       141.193.213[.]10 – IP address – Possible C2 Infrastructure

·       64.94.84[.]217 – IP address – Possible C2 Infrastructure

·       138.199.156[.]22 – IP address – C2 server

·       94.181.229[.]250 – IP address – Possible C2 Infrastructure

·       216.245.184[.]181 – IP address – Possible C2 Infrastructure

·       212.237.217[.]182 – IP address – Possible C2 Infrastructure

·       168.119.96[.]41 – IP address – Possible C2 Infrastructure

·       193.36.38[.]237 – IP address – C2 server

·       188.34.195[.]44 – IP address – C2 server

·       205.196.186[.]70 – IP address – Possible C2 Infrastructure

·       rkuagqnmnypetvf[.]top – Hostname – C2 server

·       shorturl[.]at/UB6E6 – Hostname – Possible C2 Infrastructure

·       tlgrm-redirect[.]icu – Hostname – Possible C2 Infrastructure

·       diagnostics.medgenome[.]com – Hostname – Compromised Website

·       /1741714208 – URI – Possible malicious file

·       /1741718928 – URI – Possible malicious file

·       /1743871488 – URI – Possible malicious file

·       /1741200416 – URI – Possible malicious file

·       /1741356624 – URI – Possible malicious file

·       /ttt – URI – Possible malicious file

·       /1741965536 – URI – Possible malicious file

·       /1.txt – URI – Possible malicious file

·       /1744205184 – URI – Possible malicious file

·       /1744139920 – URI – Possible malicious file

·       /1744134352 – URI – Possible malicious file

·       /1744125600 – URI – Possible malicious file

·       /1[.]php?s=527 – URI – Possible malicious file

·       34ff2f72c191434ce5f20ebc1a7e823794ac69bba9df70721829d66e7196b044 – SHA-256 Hash – Possible malicious file

·       10a5eab3eef36e75bd3139fe3a3c760f54be33e3 – SHA-1 Hash – Possible malicious file

MITRE ATT&CK Mapping

Tactic – Technique – Sub-Technique  

Spearphishing Link - INITIAL ACCESS - T1566.002 - T1566

Drive-by Compromise - INITIAL ACCESS - T1189

PowerShell - EXECUTION - T1059.001 - T1059

Exploitation of Remote Services - LATERAL MOVEMENT - T1210

Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

Automated Exfiltration - EXFILTRATION - T1020 - T1020.001

References

[1] https://www.logpoint.com/en/blog/emerging-threats/clickfix-another-deceptive-social-engineering-technique/

[2] https://www.proofpoint.com/us/blog/threat-insight/security-brief-clickfix-social-engineering-technique-floods-threat-landscape

[3] https://cyberresilience.com/threatonomics/understanding-the-clickfix-attack/

[4] https://www.group-ib.com/blog/clickfix-the-social-engineering-technique-hackers-use-to-manipulate-victims/

[5] https://www.virustotal.com/gui/ip-address/193.36.38.237/detection

[6] https://www.virustotal.com/gui/ip-address/188.34.195.44/community

[7] https://www.virustotal.com/gui/ip-address/138.199.156.22/detection

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About the author
Keanna Grelicha
Cyber Analyst

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June 4, 2025

Beyond Discovery: Adding Intelligent Vulnerability Validation to Darktrace / Attack Surface Management

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Introducing Exploit Prediction Assessment

Security teams are drowning in vulnerability alerts, but only a fraction of those issues pose a real threat. The new Exploit Prediction Assessment feature in Darktrace / Attack Surface Management helps teams cut through the noise by validating which vulnerabilities on their external attack surface can be actively exploited.

Instead of relying solely on CVSS scores or waiting for patch cycles, Exploit Prediction Assessment uses safe, targeted simulations to test whether exposed systems can be compromised, delivering fast, evidence-based results in under 72 hours.

This capability augments traditional pen testing and complements existing ASM workflows by transforming passive discovery into actionable insight. With EPA, security teams move from reacting to long lists of potential vulnerabilities to making confident, risk-based decisions on what actually matters.

Key highlights of Exploit Prediction Assessment

Simulated attacks to validate real risk

Exploit Prediction Assessment conducts safe, simulated attacks on assets with potential security vulnerabilities that have been identified by Darktrace / Attack Surface Management. This real-time testing validates your systems' susceptibility to compromise by confirming which vulnerabilities are present and exploitable on your attack surface.

Prioritize what matters most

Confirmed security risks can be prioritized for mitigation, ensuring that the most critical threats are promptly addressed. This takes the existing letter ranking system and brings it a step further by drilling down to yet another level. Even in the most overwhelming situations, teams will be able to act on a pragmatic, clear-cut plan.

Fast results, tailored to your environment

Customers set the scope of the Exploit Prediction Assessment within Darktrace / Attack Surface Management and receive the results of the surgical vulnerability testing within 72 hours. Users will see 1 of 2 shields:

1. A green shield with a check mark: Meaning no vulnerabilities were found on scanned CVEs for the asset.

2. A red shield with a red x: Meaning at least one vulnerability was found on scanned CVEs for the asset.

Why it's a game changer

Traditionally, attack surface management tools have focused on identifying exposed assets and vulnerabilities but lacked the context to determine which issues posed the greatest risk. Without context on what’s exploitable, security teams are left triaging long lists of potential risks, operating in isolation from broader business objectives. This misalignment ultimately leads to both weakened risk posture and cross team communication and execution.

This is where Continuous Threat Exposure Management (CTEM) becomes essential. Introduced by Gartner, CTEM is a framework that helps organizations continuously assess, validate, and improve their exposure to real-world threats. The goal isn’t just visibility, it’s to understand how an attacker could move through your environment today, and what to fix first to stop them.

Exploit Prediction Assessment brings this philosophy to life within Darktrace / Attack Surface Management. By safely simulating exploit attempts against identified vulnerabilities, it validates which exposures are truly at risk—transforming ASM from a discovery tool into a risk-based decision engine.

This capability directly supports the validation and prioritization phases of CTEM, helping teams focus on exploitable vulnerabilities rather than theoretical ones.  This shift from visibility to action reduces the risk of critical vulnerabilities in the technology stack being overlooked, turning overwhelming vulnerability data into focused, clear actionable insights.

As attack surfaces continue to grow and change, organizations need more than static scans they need continuous, contextual insight. Exploit Prediction Assessment ensures your ASM efforts evolve with the threat landscape, making CTEM a practical reality, not just a strategy.

Exploit Prediction Assessment in action

With Darktrace / Attack Surface Management organizations can get Exploit Prediction Assessment, and the cyber risk team no longer guesses which vulnerabilities matter most. Instead, they identify several externally exposed areas of their attack surface, then use the feature to surgically test for exploitability across these exposed endpoints. Within 72 hours, they receive a report:  

Positive outcome: Based on information in the html or the headers it seems that a vulnerable software version is running on an externally exposed infrastructure. By running a targeted attack on this infrastructure, we can confirm that it cannot be abused.

Negative outcome: Based on information in the html or the headers it seems that a vulnerable software version is running on an externally exposed infrastructure. By running a targeted attack on this infrastructure, we can confirm that it can be exploited, so we can predict it being exploited.

This second outcome changes everything. The team immediately prioritizes the exploitable asset for patching and takes the necessary adjustments to mitigate exposure until the fix is deployed.

Instead of spreading their resources thin across dozens of alerts, they focus on what poses a real threat, saving time, reducing risk, and demonstrating actionable results to stakeholders.

Conclusion

Exploit Predication Assessment bolsters Darktrace’s commitment to proactive cybersecurity. It supports intelligent prioritization of vulnerabilities, keeping organizations ahead of emerging threats. With this new addition to / Attack Surface Management, teams have another tool to empower a more efficient approach to addressing security gaps in real-time.

Stay tuned for more updates and insights on how Darktrace continues to develop a culture of proactive security across the entire ActiveAI Security Platform.

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Kelland Goodin
Product Marketing Specialist
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