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December 20, 2023

Ivanti Sentry Vulnerability | Analysis & Insights

Darktrace observed a critical vulnerability in Ivanti Sentry's cybersecurity. Learn how this almost become a huge threat and how we stopped it in its tracks.
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
Sam Lister
Specialist Security Researcher
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20
Dec 2023

In an increasingly interconnected digital landscape, the prevalence of critical vulnerabilities in internet-facing systems stands as an open invitation to malicious actors. These vulnerabilities serve as a near limitless resource, granting attackers a continually array of entry points into targeted networks.

In the final week of August 2023, Darktrace observed malicious actors validating exploits for one such critical vulnerability, likely the critical RCE vulnerability, CVE-2023-38035, on Ivanti Sentry servers within multiple customer networks. Shortly after these successful tests were carried out, malicious actors were seen delivering crypto-mining and reconnaissance tools onto vulnerable Ivanti Sentry servers.

Fortunately, Darktrace DETECT™ was able to identify this post-exploitation activity on the compromised servers at the earliest possible stage, allowing the customer security teams to take action against affected devices. In environments where Darktrace RESPOND™ was enabled in autonomous response mode, Darktrace was further able inhibit the identified post-exploitation activity and stop malicious actors from progressing towards their end goals.

Exploitation of Vulnerabilities in Ivanti Products

The software provider, Ivanti, offers a variety of widely used endpoint management, service management, and security solutions. In July and August 2023, the Norwegian cybersecurity company, Mnemonic, disclosed three vulnerabilities in Ivanti products [1]/[2]/[3]; two in Ivanti's endpoint management solution, Ivanti Endpoint Manager Mobile (EPMM) (formerly called 'MobileIron Core'), and one in Ivanti’s security gateway solution, Ivanti Sentry (formerly called 'MobileIron Sentry'):

CVE-2023-35078

  • CVSS Score: 10.0
  • Affected Product: Ivanti EPMM
  • Details from Ivanti: [4]/[5]/[6]
  • Vulnerability type: Authentication bypass

CVE-2023-35081

  • CVSS Score: 7.2
  • Affected Product: Ivanti EPMM
  • Details from Ivanti: [7]/[8]/[9]
  • Vulnerability type: Directory traversal

CVE-2023-38035

  • CVSS Score:
  • Affected Product: Ivanti Sentry
  • Details from Ivanti: [10]/[11]/[12]
  • Vulnerability type: Authentication bypass

At the beginning of August 2023, the Cybersecurity and Infrastructure Security Agency (CISA) and the Norwegian National Cyber Security Centre (NCSC-NO) provided details of advanced persistent threat (APT) activity targeting EPMM systems within Norwegian private sector and government networks via exploitation of CVE-2023-35078 combined with suspected exploitation of CVE-2023-35081.

In an article published in August 2023 [12], Ivanti disclosed that a very limited number of their customers had been subjected to exploitation of the Ivanti Sentry vulnerability, CVE-2023-38035, and on the August 22, 2023, CISA added the Ivanti Sentry vulnerability, CVE-2023-38035 to its ‘Known Exploited Vulnerabilities Catalogue’.  CVE-2023-38035 is a critical authentication bypass vulnerability affecting the System Manager Portal of Ivanti Sentry systems. The System Manager Portal, which is accessible by default on port 8433, is used for administration of the Ivanti Sentry system. Through exploitation of CVE-2023-38035, an unauthenticated actor with access to the System Manager Portal can achieve Remote Code Execution (RCE) on the underlying Ivanti Sentry system.

Observed Exploitation of CVE-2023-38035

On August 24, Darktrace observed Ivanti Sentry servers within several customer networks receiving successful SSL connections over port 8433 from the external endpoint, 34.77.65[.]112. The usage of port 8433 indicates that the System Manager Portal was accessed over the connections. Immediately after receiving these successful connections, Ivanti Sentry servers made GET requests over port 4444 to 34.77.65[.]112. The unusual string ‘Wget/1.14 (linux-gnu)’ appeared in the User-Agent headers of these requests, indicating that the command-line utility, wget, was abused to initiate the requests.

Figure 1: Event Log data for an Ivanti Sentry system showing the device breaching a range of DETECT models after contacting 34.77.65[.]112.The suspicious behavior highlighted by DETECT was subsequently investigated by Darktrace’s Cyber AI Analyst™, which was able to weave together these separate behaviors into single incidents representing the whole attack chain.

Figure 2: AI Analyst Incident representing a chain of suspicious activities from an Ivanti Sentry server.

In cases where Darktrace RESPOND was enabled in autonomous response mode, RESPOND was able to automatically enforce the Ivanti Sentry server’s normal pattern of life, thus blocking further exploit testing.

Figure 3: Event Log for an Ivanti Sentry server showing the device receiving a RESPOND action immediately after trying to 34.77.65[.]112.

The GET requests to 34.77.65[.]112 were responded to with the following HTML document:

Figure 4: Snapshot of the HTML document returned by 34.77.65[.]112.

None of the links within this HTML document were functional. Furthermore, the devices’ downloads of these HTML documents do not appear to have elicited further malicious activities. These facts suggest that the observed 34.77.65[.]112 activities were representative of a malicious actor validating exploits (likely for CVE-2023-38035) on Ivanti Sentry systems.

Over the next 24 hours, these Ivanti Sentry systems received successful SSL connections over port 8433 from a variety of suspicious external endpoints, such as 122.161.66[.]161. These connections resulted in Ivanti Sentry systems making HTTP GET requests to subdomains of ‘oast[.]site’ and ‘oast[.]live’. Strings containing ‘curl’ appeared in the User-Agent headers of these requests, indicating that the command-line utility, cURL, was abused to initiate the requests.

These ‘oast[.]site’ and ‘oast[.]live’ domains are used by the out-of-band application security testing (OAST) service, Interactsh. Malicious actors are known to abuse this service to carry out out-of-band (OOB) exploit testing. It, therefore, seems likely that these activities were also representative of a malicious actor validating exploits for CVE-2023-38035 on Ivanti Sentry systems.

Figure 5: Event Log for Ivanti Sentry system showing the device contacting an 'oast[.]site' endpoint after receiving connections from the suspicious, external endpoint 122.161.66[.]161.

The actors seen validating exploits for CVE-2023-38035 may have been conducting such activities in preparation for their own subsequent malicious activities. However, given the variety of attack chains which ensued from these exploit validation activities, it is also possible that they were carried out by Initial Access Brokers (IABs) The activities which ensued from exploit validation activities identified by Darktrace fell into two categories: internal network reconnaissance and cryptocurrency mining.

Reconnaissance Activities

In one of the reconnaissance cases, immediately after receiving successful SSL connections over port 8443 from the external endpoints 190.2.131[.]204 and 45.159.248[.]179, an Ivanti Sentry system was seen making a long SSL connection over port 443 to 23.92.29[.]148, and making wget GET requests over port 4444 with the Target URIs '/ncat' and ‘/TxPortMap’ to the external endpoints, 45.86.162[.]147 and 195.123.240[.]183.  

Figure 6: Event Log data for an Ivanti Sentry system showing the device making connections to the external endpoints, 45.86.162[.]147, 23.92.29[.]148, and 195.123.240[.]183, immediately after receiving connections from rare external endpoints.

The Ivanti Sentry system then went on to scan for open SMB ports on systems within the internal network. This activity likely resulted from an attacker dropping a port scanning utility on the vulnerable Ivanti Sentry system.

Figure 7: Event Log data for an Ivanti Sentry server showing the device breaching several DETECT models after downloading a port scanning tool from 195.123.240[.]183.

In another reconnaissance case, Darktrace observed multiple wget HTTP requests with Target URIs such as ‘/awp.tar.gz’ and ‘/resp.tar.gz’ to a suspicious, external server (78.128.113[.]130).  Shortly after making these requests, the Ivanti Sentry system started to scan for open SMB ports and to respond to LLMNR queries from other internal devices. These behaviors indicate that the server may have installed an LLMNR poisoning tool, such as Responder. The Ivanti Sentry server also went on to conduct further information-gathering activities, such as LDAP reconnaissance, HTTP-based vulnerability scanning, HTTP-based password searching, and RDP port scanning.

Figure 8: Event Log data for an Ivanti Sentry system showing the device making connections to 78.128.113[.]130, scanning for an open SMB port on internal endpoints, and responding to LLMNR queries from internal endpoints.

In cases where Darktrace RESPOND was active, reconnaissance activities resulted in RESPOND enforcing the Ivanti Sentry server’s pattern of life.

Figure 9: Event Log data for an Ivanti Sentry system receiving a RESPOND action as a result of its SMB port scanning activity.
Figure 10: Event Log data for an Ivanti Sentry system receiving a RESPOND action as a result of its LDAP reconnaissance activity.

Crypto-Mining Activities

In one of the cryptomining cases, Darktrace detected an Ivanti Sentry server making SSL connections to aelix[.]xyz and mining pool endpoints after receiving successful SSL connections over port 8443 from the external endpoint, 140.228.24[.]160.

Figure 11: Event Log data for an Ivanti Sentry system showing the device contacting aelix[.]xyz and mining pool endpoints immediately after receiving connections from the external endpoint, 140.228.24[.]160.

In a cryptomining case on another customer’s network, an Ivanti Sentry server was seen making GET requests indicative of Kinsing malware infection. These requests included wget GET requests to 185.122.204[.]197 with the Target URIs ‘/unk.sh’ and ‘/se.sh’ and a combination of GET and POST requests to 185.221.154[.]208 with the User-Agent header ‘Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/99.0.4844.51 Safari/537.36’ and the Target URIs, ‘/mg’, ‘/ki’, ‘/get’, ‘/h2’, ‘/ms’, and ‘/mu’. These network-based artefacts have been observed in previous Kinsing infections [13].

Figure 12: Event Log data for an Ivanti Sentry system showing the device displaying likely Kinsing C2 activity.

On customer environments where RESPOND was active, Darktrace was able to take swift autonomous action by blocking cryptomining connection attempts to malicious command-and-control (C2) infrastructure, in this case Kinsing servers.

Figure 13: Event Log data for an Ivanti Sentry server showing the device receiving a RESPOND action after attempting to contact Kinsing C2 infrastructure.

Fortunately, due to Darktrace DETECT+RESPOND prompt identification and targeted actions against these emerging threats, coupled with remediating steps taken by affected customers’ security teams, neither the cryptocurrency mining activities nor the network reconnaissance activities led to significant disruption.  

Figure 14: Timeline of observed malicious activities.

Conclusion The inevitable presence of critical vulnerabilities in internet-facing systems underscores the perpetual challenge of defending against malicious intrusions. The near inexhaustible supply of entry routes into organizations’ networks available to malicious actors necessitates a more proactive and vigilant approach to network security.

While it is, of course, essential for organizations to secure their digital environments through the regular patching of software and keeping abreast of developing vulnerabilities that could impact their network, it is equally important to have a safeguard in place to mitigate against attackers who do manage to exploit newly discovered vulnerabilities.

In the case of Ivanti Sentry, Darktrace observed malicious actors validating exploits against affected servers on customer networks just a few days after the public disclosure of the critical vulnerability.  This activity was followed up by a variety of malicious and disruptive, activities including cryptocurrency mining and internal network reconnaissance.

Darktrace DETECT immediately detected post-exploitation activities on compromised Ivanti Sentry servers, enabling security teams to intervene at the earliest possible stage. Darktrace RESPOND, when active, autonomously inhibited detected post-exploitation activities. These DETECT detections, along with their accompanying RESPOND interventions, prevented malicious actors from being able to progress further towards their likely harmful objectives.

Credit to Sam Lister, Senior Cyber Analyst, and Trent Kessler, SOC Analyst  

Appendices

MITRE ATT&CK Mapping

Initial Access techniques:

  • Exploit Public-Facing Application (T1190)

Credential Access techniques:

  • Unsecured Credentials: Credentials In Files (T1552.001)
  • Adversary-in-the-Middle: LLMNR/NBT-NS Poisoning and SMB Relay (T1557.001)

Discovery

  • Network Service Discovery (T1046)
  • Remote System Discovery (T1018)
  • Account Discovery: Domain Account (T1087.002)

Command and Control techniques:

  • Application Layer Protocol: Web Protocols (T1071.001)
  • Ingress Tool Transfer (T1105)
  • Non-Standard Port (T1571)
  • Encrypted Channel: Asymmetric Cryptography (T1573.002)

Impact techniques

  • Resource Hijacking (T1496)
List of IoCs

Exploit testing IoCs:

·      34.77.65[.]112

·      Wget/1.14 (linux-gnu)

·      cjjovo7mhpt7geo8aqlgxp7ypod6dqaiz.oast[.]site • 178.128.16[.]97

·      curl/7.19.7 (x86_64-redhat-linux-gnu) libcurl/7.19.7 NSS/3.27.1 zlib/1.2.3 libidn/1.18 libssh2/1.4.2

·      cjk45q1chpqflh938kughtrfzgwiofns3.oast[.]site • 178.128.16[.]97

·      curl/7.29.0

Kinsing-related IoCs:

·      185.122.204[.]197

·      /unk.sh

·      /se.sh

·      185.221.154[.]208

·      185.221.154[.]208

·      45.15.158[.]124

·      Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/99.0.4844.51 Safari/537.36

·      /mg

·      /ki

·      /get

·      /h2

·      /ms

·      /mu

·      vocaltube[.]ru • 185.154.53[.]140

·      92.255.110[.]4

·      194.87.254[.]160

Responder-related IoCs:

·      78.128.113[.]130

·      78.128.113[.]34

·      /awp.tar.gz

·      /ivanty

·      /resp.tar.gz

Crypto-miner related IoCs:

·      140.228.24[.]160

·      aelix[.]xyz • 104.21.60[.]147 / 172.67.197[.]200

·      c8446f59cca2149cb5f56ced4b448c8d (JA3 client fingerprint)

·      b5eefe582e146aed29a21747a572e11c (JA3 client fingerprint)

·      pool.supportxmr[.]com

·      xmr.2miners[.]com

·      xmr.2miners[.]com

·      monerooceans[.]stream

·      xmr-eu2.nanopool[.]org

Port scanner-related IoCs:

·      122.161.66[.]161

·      192.241.235[.]32

·      45.86.162[.]147

·      /ncat

·      Wget/1.14 (linux-gnu)

·      45.159.248[.]179

·      142.93.115[.]146

·      23.92.29[.]148

·      /TxPortMap

·      195.123.240.183

·      6935a8d379e086ea1aed159b8abcb0bc8acf220bd1cbc0a84fd806f14014bca7 (SHA256 hash of downloaded file)

Darktrace DETECT Model Breaches

·      Anomalous Server Activity / New User Agent from Internet Facing System

·      Device / New User Agent

·      Anomalous Connection / New User Agent to IP Without Hostname

·      Device / New User Agent and New IP

·      Anomalous Connection / Application Protocol on Uncommon Port

·      Anomalous Connection / Callback on Web Facing Device

·      Compromise / High Volume of Connections with Beacon Score

·      Compromise / Large Number of Suspicious Failed Connections

·      Compromise / High Volume of Connections with Beacon Score

·      Compromise / Beacon for 4 Days

·      Compromise / Agent Beacon (Short Period)

·      Device / Large Number of Model Breaches

·      Anomalous Server Activity / Rare External from Server

·      Compromise / Large Number of Suspicious Successful Connections

·      Compromise / Monero Mining

·      Compromise / High Priority Crypto Currency Mining

·      Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

·      Device / Internet Facing Device with High Priority Alert

·      Device / Suspicious SMB Scanning Activity

·      Device / Internet Facing Device with High Priority Alert

·      Device / Network Scan

·      Device / Unusual LDAP Bind and Search Activity

·      Compliance / Vulnerable Name Resolution

·      Device / Anomalous SMB Followed By Multiple Model Breaches

·      Device / New User Agent To Internal Server

·      Anomalous Connection / Suspicious HTTP Activity

·      Anomalous Connection / Unusual Internal Connections

·      Anomalous Connection / Suspicious HTTP Activity

·      Device / RDP Scan

·      Device / Large Number of Model Breaches

·      Compromise / Beaconing Activity To External Rare

·      Compromise / Beacon to Young Endpoint

·      Anomalous Connection / Suspicious HTTP Activity

·      Compromise / Suspicious Internal Use Of Web Protocol

·      Anomalous File / EXE from Rare External Location

·      Anomalous File / Internet Facing System File Download

·      Device / Suspicious SMB Scanning Activity

·      Device / Internet Facing Device with High Priority Alert

·      Device / Network Scan

·      Device / Initial Breach Chain Compromise

References

[1] https://www.mnemonic.io/resources/blog/ivanti-endpoint-manager-mobile-epmm-authentication-bypass-vulnerability/
[2] https://www.mnemonic.io/resources/blog/threat-advisory-remote-file-write-vulnerability-in-ivanti-epmm/
[3] https://www.mnemonic.io/resources/blog/threat-advisory-remote-code-execution-vulnerability-in-ivanti-sentry/
[4] https://www.ivanti.com/blog/cve-2023-35078-new-ivanti-epmm-vulnerability
[5] https://forums.ivanti.com/s/article/CVE-2023-35078-Remote-unauthenticated-API-access-vulnerability?language=en_US
[6] https://forums.ivanti.com/s/article/KB-Remote-unauthenticated-API-access-vulnerability-CVE-2023-35078?language=en_US
[7] https://www.ivanti.com/blog/cve-2023-35081-new-ivanti-epmm-vulnerability
[8] https://forums.ivanti.com/s/article/CVE-2023-35081-Arbitrary-File-Write?language=en_US
[9] https://forums.ivanti.com/s/article/KB-Arbitrary-File-Write-CVE-2023-35081?language=en_US
[10] https://www.ivanti.com/blog/cve-2023-38035-vulnerability-affecting-ivanti-sentry
[11] https://forums.ivanti.com/s/article/CVE-2023-38035-API-Authentication-Bypass-on-Sentry-Administrator-Interface?language=en_US
[12] https://forums.ivanti.com/s/article/KB-API-Authentication-Bypass-on-Sentry-Administrator-Interface-CVE-2023-38035?language=en_US
[13] https://isc.sans.edu/diary/Your+Business+Data+and+Machine+Learning+at+Risk+Attacks+Against+Apache+NiFi/29900

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
Sam Lister
Specialist Security Researcher

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May 27, 2026

How to Evaluate AI Vendors: 5 Key categories for AI Adoption

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Understanding the AI buyers’ market

AI adoption has become a central topic of discussion in boardrooms, drawing growing interest from business leaders. Ultimately, organizations hope that an investment in AI technology will have tremendous returns. However, the process of buying an AI solution is not as straight forward as it appears on the surface.  

While business leaders may be eager to improve productivity across their operations, practitioners responsible for evaluating and selecting AI solutions may not always have the visibility or technical understanding needed to make the right decisions for their business. What is typically marketed as a holistic solution to their most critical problems is usually followed by uncertainty when AI tools are finally operationalized in real environments.

This guide is intended to support security leaders who are under growing pressure to adopt AI tools while navigating complex terminology, vendor claims, and increasingly crowded buying cycles. Ultimately, the goal is to help organizations evaluate and adopt AI in a safe, effective, and well-governed way. To support this, we’ve structured the evaluation framework across five key categories:

  1. Governance, safety, and data controls
  1. Data gathering and training
  1. Model and technique choice
  1. Performance and accuracy validation    
  1. Interpretability, adjustability, and transparency    

What buying AI looks like in cybersecurity

While investing in AI can bring immense benefits to your security team, first-time buyers of AI cybersecurity solutions may not know where to start. They will have to determine the type of tool they want, know the options available, and evaluate vendors. Research and understanding are critical to ensure purchases are worth the investment.  

With acceleration in AI adoption, accompanied by the recent boom in agentic AI and autonomous agents, CISOs must look “beneath the hood" of these tools to understand how they work, how they are governed, and to ensure the system is secure and compliant with internal policies.

Challenges in the AI buyers’ marketplace  

The AI security software market is buzzing with hype and flashy promises, which, understandably, needs to be addressed with due diligence. Potential buyers, especially in the cybersecurity space, are hesitant when it comes to allowing AI autonomous capabilities across their workflows, and a lack of vendor transparency can exacerbate those feelings.  

Reinforcing this sentiment, research from this year's Darktrace’s State of AI Cybersecurity report shows where confidence and hesitancy emerge amongst potential buyers. On the one hand, security professionals agree that they have good visibility into the logic and reasoning processes their AI solutions use. However, they lack the explainability and trust to allow AI to take independent remedial action.

  • 89% say they have good visibility into the reasoning behind the outputs generated by AI solutions
  • 92% say they need to understand how a defensive AI tool makes decisions before they can trust it
  • Only 14% say they allow AI to act independently, performing autonomous actions without human approval
  • 74% say they are limiting the autonomy of AI taking action in their SOC until explainability improves

Given the desire for trust and explainability we are seeing from buyers, it's important for them to be equipped with the right questions to ask vendors during an assessment or POV of AI tools in order to demystify marketing hype from real operational outcomes.

Below is a list of categories in which buyers can assess AI vendors or AI Service Providers (AISPs) to help reach safe adoption and maximize their ROI.  

5 categories of AI vendor assessment

Darktrace groups these AI-related questions into 5 categories: governance, data and training, model and technique choice, performance validation, and interpretability and adjustability. By asking questions regarding each of these 5 categories, buyers can gain a deeper understanding of how an AISP’s systems work and whether they suit their business requirements.

Governance, safety, and data controls

Governance of AI systems is critical for all AISPs. Whether their platform is based around a single model, or is a more complex, composite AI solution, strong governance is essential to ensure the system is safe, robust, and reliable.

A simple question you could ask is:

What AI governance policies and frameworks do you follow, and/or certifications do you currently maintain?

For more questions you can ask vendors, download the full guide here.

Darktrace is certified to the ISO/IEC 42001 standard, the world’s first AI Management System (AIMS) standard. ISO/IEC 42001 addresses the unique ethical and technical challenges AI poses by setting out a structured way to manage risks such as transparency, accuracy, and misuse. This includes a commitment to ethical AI development, and effective management and monitoring of AI systems both prior to and continually after release.

Data gathering and training

Accurate, meaningful, and unbiased data gathering is the first important step in producing any AI system. An AI model trained using inaccurate, unbalanced, or poor-quality training data will fail to perform optimally.

To alleviate concerns regarding training data quality, a question you could ask is:

What steps do you take to prevent bias in your AI models and training data?

For more questions, download the full guide here.

AISPs should be able to provide information about the steps taken, workflows followed, and auditing performed to reduce AI bias where appropriate. While it’s sometimes impossible to fully remove bias from an AI model, appropriate actions should be taken to mitigate or reduce bias where relevant.

Model and technique choice

Different AI techniques are optimal for different tasks. For example, research from Gartner suggests that relying on a single “one-size-fits-all" model can lead to data gaps, especially in highly specialized domains.

To achieve more accurate and robust AI solutions, AI leaders should move beyond using just one model or technique, embrace composite AI practices, and adopt a holistic AI system perspective.

A straightforward question you could ask is simply:

What type(s) of AI model(s) do you utilize in your solution?

For more questions, download the full guide here.

While specific detailed information about custom systems used by AISPs is likely proprietary, buyers should expect vendors to be able to provide an overview of the broad techniques used. This will allow you as a buyer to determine if the type of model is appropriate for your use case.

Performance and accuracy validation  

Testing and evaluation of performance is essential for all AI systems. Performance analysis should be performed both before release and continually after release to identify potential data or model drift.  

A question you could ask to understand an AISPs testing workflow is:

How do you audit, test, evaluate, verify, and validate your AI model outputs?

For more questions, download the full guide here.

Testing workflows will likely vary depending on the type of model – measurements relevant to one system may not always be relevant to others. Assessment of systems should also extend beyond these standard accuracy and robustness tests, and should also feature physical performance, such as latency and resource consumption.  

Interpretability, adjustability, and transparency  

AI systems are typically a black box, simply providing an output without an explanation of how that output was attained. Interpretability and transparency are critical to ensure that both SOC teams and end-users trust the outputs of a system to be accurate and meaningful.

A question you could ask is:

How do you promote a trust relationship between human analysts and AI outputs?

For more questions, download the full guide here.

In the context of cybersecurity, trust and interpretability are even more essential. This is particularly relevant for generative AI-based systems (including most AI Agents), where the risk of hallucination can reduce trust in responses.

Cybersecurity systems often need to perform autonomous actions to block incoming threats – an email filtering system may hold potentially dangerous emails; a firewall may block malicious inbound connections. If SOC teams can’t trust these systems to perform accurately, these systems may be limited or disabled, critically reducing their defensive power.

Darktrace as an AI-native cybersecurity vendor

Darktrace has been building and applying AI in cybersecurity for over a decade, developing its capabilities alongside an increasingly complex and fast‑moving threat landscape. This experience has resulted in a mature, multi-layered approach to AI, which continuously learns the normal patterns of each organization to understand behavior, interpret context, and identify meaningful deviations — without relying on predefined rules or known attack signatures. Over time, this has enabled a proven behavioral understanding that helps uncover subtle signals of risk that may otherwise be missed.

With the backing of our ISO/IEC 42001 certification, stakeholders, customers, and partners can be confident that Darktrace is responsibly, ethically, and safely developing its AI systems, and managing the use of AI in day-to-day operations in a compliant and secure manner.  

Explore the principles behind Darktrace’s responsible AI approach, informed by collaboration with global experts in academia and governments, detailing how accountability, explainability, and continuous validation are built into its cybersecurity technology.

How Darktrace secures AI systems

Darktrace now brings these capabilities to monitor and respond to risk generated from AI systems across organizations with Darktrace / SECURE AI. This solution analyzes how prompts, agents, and systems are used within the context of each organization, bringing every AI interaction into a single view. This unique approach helps teams understand intent, assess risk, protect sensitive data, and enforce policy across both human and AI agent activity.

Stay up to date

Sign up for the Secure AI Readiness Program here: This gives you exclusive access to the latest news on the latest AI threats, updates on emerging approaches shaping AI security, and insights into the latest innovations, including Darktrace’s ongoing work in this area.

Ready to talk with a Darktrace expert on securing AI? Register here to receive practical guidance on the AI risks that matter most to your business, paired with clarity on where to focus first across governance, visibility, risk reduction, and long-term readiness.  

Further Reading on AI in cybersecurity

When deciding to invest in an AI solution, it’s important to understand what this means for you and your organization. The questions presented here are only a starting point in understanding an AI solution and whether it is appropriate for your use case.  

Gain deeper knowledge on applications of AI in cybersecurity and Darktrace’s multi-layered AI in the AI Arsenal White Paper.

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May 26, 2026

Journey of a Threat: How Multi-Layered AI Works in Darktrace / EMAIL

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Darktrace / EMAIL is an implementation of the Darktrace methodology – a multi-layered AI system built into a single product. As with other Darktrace products, Darktrace / EMAIL learns the expected behaviours of an organization and its employees to identify novel threats and anomalous activity.

The diagram below represents the architecture of Darktrace / EMAIL’s multi-layered AI: a structured visualization of how intelligence is built, step by step, from raw data to actionable insight. Each layer plays a distinct role, feeding into the next: collecting data, understanding behaviour, analysing intent, making decisions, and presenting clear outcomes.

It all starts with an email

In this blog, we’ll follow a malicious email as it passes through the Darktrace / EMAIL system, showing exactly what happens as it travels through each layer of the pyramid, from basic data extraction to AI-powered metric creation, and finally deciding on any autonomous actions.

Let’s take this example email. As an end-user, you can see that this is an obvious extortion attempt where an adversary is threatening legal action if money isn’t paid within 24 hours, but how does Darktrace figure that out?

Part 1: Data Gathering

Processing of an email begins on point-of-transit for all inbound, outbound, or lateral emails. The first step is to extract information directly. This includes taking information from the headers (such as sending and receiving addresses, sender IP address, routing, and authentication protocols), as well as extraction of raw HTML and CSS data from the email itself.

This directly extracted information only allows for immediate surface level analysis, such as identifying signature-based attacks (known malicious addresses / domains), but is insufficient for identifying novel threats, complex attacks, or potential email or vendor compromise. This is where Darktrace’s AI analysis shines.

In this example, the SPF, DKIM, and DMARC authentication all passed successfully, showing that even malicious emails can still bypass these signature-based checks. Even with this success, Darktrace will continue to analyse the email.

Diving deeper into the technical information, we can see further information extracted from the headers, including aggregations from the header information, historical calculations such as the frequency and volume of emails to and from a particular domain, and much more.

Part 2: Social Graphing

Social Graphing involves the analysis of sending and receiving behaviours of different mailboxes to create peer-groups. Mailboxes who often send and receive to and from the same mailboxes, or exhibit other correlated behaviours, will be clustered together using a collection of unsupervised AI clustering systems. These groups may represent uses in the same teams who perform similar activity, groups of external facing mailboxes which often receive unsolicited emails, or groups of VIP users (such as C-suite or executives).

Social graphing is an essential component of Darktrace’s pattern of life analysis. This clustering allows Darktrace to understand the responsibilities of individuals – for example, behaviours which are anomalous for one group of users may be completely expected of another group.

In our example, the email was sent to 3 different users within the organization. As part of the social graphing, an “Association Anomaly” is calculated which indicates the likelihood that these users would receive emails from this user or domain, based on historical patterns.

Part 3: Metric Calculation

Metrics are calculated for every email, representing more complex characteristics of an email which can’t be directly extracted. Darktrace / EMAIL features over 1000 unique metrics, calculated both algorithmically and using an ensemble of AI systems.

Algorithmically calculated (non-AI) metrics include further historical calculations, and counts of features such as code blocks, and hidden text, to name a few.

AI-driven metrics include Inducement Classification which uses Natural Language Processing to identify potential phishing, solicitation, or extortion attempts; Named Entity Recognition to identify PII and other sensitive data within an email to support Data Loss Prevention; and many more.

We can follow our example email through this process and view the outcome of these metric calculations. Looking at the language metrics for this email, we can see that our email has reported a high extortion inducement, along with identification of banking information and language indicating urgency.

Part 4: Evaluation and Combination Engine (models)

Once all metrics have been calculated for an email, it gets sent to an evaluation and combination engine where the metrics are compared against blocks of logic to determine if an email contains a threat. One key model which alerted for this example message was a model to tag and block extortion attempts.

Since our example email has a high inducement score for extortion, along the presence of a bitcoin wallet address in the message, this model alerts. When a model in the engine is activated, actions are taken – in this case adding a tag to the email to flag it as extortion in the console and hold the email to prevent it from reaching the end-user mailbox.

Part 5: Meta-Modelling and Actions

Once the models have been run, the actions are taken against the email. If the email hasn’t been blocked or held, this is the point where it will reach the end-user's mailbox.

In the Darktrace / EMAIL UI, all actions models which alerted for an email and actions taken as a result can be seen. At the top of this page, you can see the alert indicating an extortion attempt along with the action to hold the message.

Alongside this, a meta-classifier is used to calculate an overall anomaly score for each email, based on how much the email differs from the pattern of life for the user. The score of the email is boosted by any actions that have taken place.

Part 6: Campaign Clustering

All emails are passed through the Darktrace / EMAIL campaign clustering system. This system creates clusters based on related features within the emails to identify groups of emails with the same sender or intent.

In our case, the email was identified as part of a campaign, alongside other emails which were also identified as extortion attempts against a small group of recipients.

Email campaigns may have additional actions applied to them if the campaign is deemed malicious, and in this case, you can see that the autonomous response was to hold all emails in the campaign. This means that if an email manages to avoid being blocked in the evaluation and combination engine but gets identified as part of the campaign, the hold action will be applied to it retroactively.

Part 7: Cyber AI Analyst

Darktrace’s Cyber AI Analyst presents key information and anomaly indicators for each email, such as further information about authentication, specific metrics, or other identified anomalies and mismatches.

Cyber AI Analyst can also utilize data from Darktrace / EMAIL to enhance its investigation of incidents from other Darktrace products, correlating relevant information to build a fuller picture. More information about the Cyber AI Analyst is available in the Darktrace AI Arsenal.

Part 8: Data Presentation (UI)

Once all processing has taken place against the email, it is presented in the Darktrace / EMAIL UI. Here, members of the SOC team can investigate incidents and anomalies, interact with malicious emails to see why they were blocked, and much more.

Our email stands out here with its 100 anomaly score. Every email which passes through a Darktrace / EMAIL will undergo the same thorough and rigorous analysis to identify potential risks, apply autonomous actions where required, and will ultimately be assigned a score to be displayed here. By providing a single overall score in the UI, rather than presenting emails in full, Darktrace / EMAIL allows SOC teams to more easily identify which emails are most important to investigate, increasing efficiency and reducing alert fatigue.

Take the next step

Many email security tools on the market that claim to be AI-driven are in fact bolting AI onto attack-centric approaches, which rely on automating the identification of known threats. These approaches struggle, and will continue to struggle, with adapting to novel, AI-generated threats.

By analyzing every email within its deeply integrated, multi-layered AI system, Darktrace / EMAIL is able to identify the subtle threats that others miss. This depth not only improves detection accuracy, but enables confident, autonomous action, giving security teams clearer insight into AI outcomes and greater control while supporting users.

For a full deep dive into each stage of the AI system, check out the white paper: A Guide to the Multi-Layered AI in Darktrace / EMAIL

Learn more about securing AI in your enterprise.

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About the author
Jamie Bali
Technical Author (AI) Developer
Your data. Our AI.
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