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May 9, 2023

Breaking Down "ICES": An Umbrella Term With Wide Variety

Integrated Cloud Email Security (ICES) can be an effective email security solution, but Darktrace/Email's self-learning AI should be your solution of choice.
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.
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Dan Fein
VP, Product
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09
May 2023

While organizing email security solutions into categories can help security teams understand the types of products available, it can also lead to generalizations that overlook important differences within those categories and can become like comparing apples to oranges.

This is true for the Integrated Cloud Email Security (ICES) category. Among the products that qualify, there are important variations in approach that can mean the difference between stopping a novel phishing attack on the first encounter and catching it as many as 13 days later.

These distinctions highlight that not all ICES products and not all AI tools are made equal, and it’s critical to look deeper than the “ICES” label when examining an email security solution. 

What is an ICES solution?

Gartner devised the term ICES in 2021 to describe an advanced email security that augments the native capabilities of email providers by using API access to analyze email content without requiring changing the MX record. 

In other words, ICES solutions integrate with an organization’s cloud email provider to filter out malicious emails.

ICES has risen in popularity as more and more organizations shift to cloud-based or hybrid email servers, and encounter new, more sophisticated threats. Organizations pair ICES with improved native capabilities of email providers. For example, in the 2023 Market Guide for Email Security, Gartner acknowledged that “Microsoft, in particular, continues to make significant investments in improving protection effectiveness and providing better configuration guidance.” 

Native capabilities can detect traditional indicators of compromise, while ICES products can detect nuanced attacks. They integrate directly with cloud-based email providers, meaning emails do not have to be rerouted for analysis, therefore reducing the time security teams would have to spend configuring and maintaining that connection or risking operational outage. 

ICES protects against sophisticated attacks

Before the rise of ICES, the mainstream email security solutions were Secure Email Gateways (SEGs), which can be characterized as tools that rely on historic data to create rules and signatures. This purely reactive approach cannot contend with the current email threat landscape, which includes attacks that abuse legitimate services, originate from compromised known senders, or are entirely novel. They also struggle to detect multi-stage attacks and insider threats

Instead, ICES products use natural language processing and natural language understanding to identify social engineering like business email compromises, spoofing, supply chain attacks, account takeovers, and more.  However, although ICES products can detect more sophisticated threats than SEGs, not all of them can stop entirely unknown attacks. 

Achieving bespoke security with AI that understands you

Even though several ICES products rely on machine learning to identify and stop malicious emails, not all AI is the same. Typically, other vendors’ AIs are trained on insights pulled from across their respective customer-bases and past attacks. However, this does not account for nuanced distinctions that arise from organizations’ sizes, industries, or even the individual employees working at each company. 

Instead, Darktrace understands you. Self-Learning AI™ focuses on the organization it is installed in, instead of generalizing across a wider pool. Darktrace even learns on a granular level, building profiles of every individual employee by analyzing behaviors like how they typically communicate, where and when they log in, the tone and sentiment of their emails, file and link sharing patterns, and hundreds of other signals. This level of specificity ensures that the email security is tailored to each specific organization. 

The ability to learn employee behavior allows Darktrace to detect what is not normal, therefore revealing sophisticated threats on the first encounter. It can detect all types of attacks, including BEC, account takeover, insider threat, compromised internal accounts, and even human error. 

But it’s the ability to stop novel attacks upon the first encounter that sets it apart. Darktrace/Email™ can detect novel email attacks an average of 13 days earlier than email security tools that are trained on knowledge of historical threats. 

Moreover, Darktrace can take precise action to respond to threats, beyond simply allowing or blocking a suspicious email. The AI makes micro-decisions to neutralize only the malicious components of emails. For example, it might flatten an attached PDF, rewrite a shared link, or file an email as junk. 

Darktrace/Email goes further than other ICES by considering the employee experience. With an employee-AI feedback loop, the AI can fine-tune security based on the employees while also providing inline security awareness training in real-time and with real-life examples. By engaging down to the employee level, Darktrace AI can even leverage personalized insights for productivity gains, sorting out graymail based on how each user prefers to interact with it. 

Putting the “I” in “ICES”

Many ICES vendors emphasize the “integrated” part of the acronym, however Darktrace excels at this. Since Darktrace can be installed anywhere a company has data, it can natively interact across the digital estate, saving the security team time and resources otherwise spent learning various dashboards and languages, correlating data across different areas, and manually monitoring daily activity. Darktrace/Email can also integrate with external tools, including SIEMs and SOARs, to further enhance workflows

Moreover, since combining ICES solutions with native security email capabilities creates a hardened security posture, Darktrace/Email benefits from its strong, established integration with Microsoft

Introducing flexibility to ICES deployments

Finally, the security and integration capabilities of Darktrace/Email deploy easily. In the 2023 Market Guide for Email Security, Gartner predicted that “by 2025, 20% of anti-phishing solutions will be delivered via API integration with the email platform, up from less than 5% today.” Darktrace/Email can be rolled out via API or API + Journaling in Microsoft 365, whichever better fits the organization’s needs.

While all ICES products are API-based, that does not mean they are AI-first, or are using the best AI approach. Even some SEGs can deploy via API. That means that the ability to deploy via API does not guarantee a level of security that can stop the most sophisticated threats. Security teams should look beyond deployment method and select the ICES and AI solutions that provide tailored, effective security. 

Finding nuance as an ICES solution

Email security continues to advance in tandem with the threat landscape and organizations’ digital infrastructures. ICES solutions are supplanting SEGs as the mainstream email security solutions, however that broad category includes a range of tools with varying applications of AI. These differences make it critical to not put all ICES products in the same basket. 

Darktrace/Email is the only ICES solution that uses Self-Learning AI to detect all types of email threats, including novel attacks, within seconds.

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

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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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Proactive Security

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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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About the author
Kelland Goodin
Product Marketing Specialist
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