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August 2, 2023

Darktrace's Detection of Ransomware & Syssphinx

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02
Aug 2023
Read how Darktrace identified an attack technique by the threat group, Syssphinx. Learn how Darktrace's quick identification process can spot a threat.

Introduction

As the threat of costly cyber-attacks continues represent a real concern to security teams across the threat landscape, more and more organizations are strengthening their defenses with additional security tools to identify attacks and protect their networks. As a result, malicious actors are being forced to adapt their tactics, modify existing variants of malicious software, or utilize entirely new variants.  

Symantec recently released an article about Syssphinx, the financially motivated cyber threat group previously known for their point-of-sale attacks. Syssphinx attempts to deploy ransomware on customer networks via a modified version of their ‘Sardonic’ backdoor. Such activity highlights the ability of threat actors to alter the composition and presentation of payloads, tools, and tactics.

Darktrace recently detected some of the same indicators suggesting a likely Syssphinx compromise within the network of a customer trialing the Darktrace DETECT™ and RESPOND™ products. Despite the potential for variations in the construction of backdoors and payloads used by the group, Darktrace’s anomaly-based approach to threat detection allowed it to stitch together a detailed account of compromise activity and identify the malicious activity prior to disruptive events on the customer’s network.

What is Syssphinx?

Syssphinx is a notorious cyber threat entity known for its financially motivated compromises.  Also referred to as FIN8, Syssphinx has been observed as early as 2016 and is largely known to target private sector entities in the retail, hospitality, insurance, IT, and financial sectors.[1]

Although Syssphinx primarily began focusing on point-of-sale style attacks, the activity associated with the group has more recently incorporated ransomware variants into their intrusions in a potential bid to further extract funds from target organizations.[2]

Syssphinx Sardonic Backdoor

Given this gradual opportunistic incorporation of ransomware, it should not be surprising that Syssphinx has slowly expanded its repertoire of tools.  When primarily performing point-of-sale compromises, the group was known for its use of point-of-sale specific malwares including BadHatch, PoSlurp/PunchTrack, and PowerSniff/PunchBuggy/ShellTea.[3]

However, in a seeming response to updates in detection systems while using previous indicators of compromise (IoCs), Syssphinx began to modify its BadHatch malware.  This resulted in the use of a C++ derived backdoor known as “Sardonic”, which has the ability to aggregate host credentials, spawn additional command sessions, and deliver payloads to compromised devices via dynamic-link library (DLL).[4],[5]

Analysis of the latest version of Sardonic reveals further changes to the malware to elude detection. These shifts include the implementation of the backdoor in the C programming language, and additional over-the-network communication obfuscation techniques. [6]

During the post-exploitation phase, the group tends to rely on “living-off-the-land” tactics, whereby an attacker utilizes tools already present within the organization’s digital environment to avoid detection. Syssphinx seems to utilize system-native tools such as PowerShell and the Windows Management Instrumentation (WMI) interface.[7] It is also not uncommon to see Windows-based vulnerability exploits employed on compromised devices. This has been observed by researchers who have examined previous iterations of Syssphinx backdoors.[8] Syssphinx also appears to exhibit elements of strategic patience and discipline in its operations, with significant time gaps in operations noted by researchers. During this time, it appears likely that updates and tweaks were applied to Syssphinx payloads.

Compromise Details

In late April 2023, Darktrace identified an active compromise on the network of a prospective customer who was trialing Darktrace DETECT+RESPOND. The customer, a retailer in EMEA with hundreds of tracked devices, reached out to the Darktrace Analyst team via the Ask the Expert (ATE) service for support and further investigation, following the encryption of their server and backup data storage in an apparent ransomware attack. Although the encryption events fell outside Darktrace’s purview due to a limited set up of trial appliances, Darktrace was able to directly track early stages of the compromise before exfiltration and encryption events began. If a full deployment had been set up and RESPOND functionality had been configured in autonomous response mode, Darktrace may have helped mitigate such encryption events and would have aided in the early identification of this ransomware attack.

Initial Intrusion and Establishment of Command and Control (C2) Infrastructure

As noted by security researchers, Syssphinx largely relies on social engineering and phishing emails to deliver its backdoor payloads. As there were no Darktrace/Email™ products deployed for this customer, it would be difficult to directly observe the exact time and manner of initial payload delivery related to this compromise. This is compounded by the fact that the customer had only recently began using Darktrace’s products during their trial period. Given the penchant for patience and delay by Syssphinx, it is possible that the intrusion began well before Darktrace had visibility of the organization’s network.

However, beginning on April 30, 2023, at 07:17:31 UTC, Darktrace observed the domain controller dc01.corp.XXXX  making repeated SSL connections to the endpoint 173-44-141-47[.]nip[.]io. In addition to the multiple open-source intelligence (OSINT) flags for this endpoint, the construction of the domain parallels that of the initial domain used to deliver a backdoor, as noted by Symantec in their analysis (37-10-71-215[.]nip[.]io). This activity likely represented the initial beaconing being performed by the compromised device. Additionally, an elevated level of incoming external data over port 443 was observed during this time, which may be associated with the delivery of the Sardonic backdoor payload. Given the unusual use of port 443 to perform SSH connections later seen in the kill chain of this attack, this activity could also parallel the employment of embedded backdoor payloads seen in the latest iteration of the Sardonic backdoor noted by Symantec.

Figure 1: Graph of the incoming external data surrounding the time of the initial establishment of command and control communication for the domain controller. As seen in the graph, the spike in incoming external data during this time may parallel the delivery of Syssphinx Sardonic backdoor.

Regardless, the domain controller proceeded to make repeated connections over port 443 to the noted domain.

Figure 2: Breach event log for the domain controller making repeated connections over port 443 to the rare external destination endpoint in constitute the establishment of C2 communication.

Internal Reconnaissance/Privilege Escalation

Following the establishment of C2 communication, Darktrace detected numerous elements of internal reconnaissance. On Apr 30, 2023, at 22:06:26 UTC, the desktop device desktop_02.corp.XXXX proceeded to perform more than 100 DRSGetNCChanges requests to the aforementioned domain controller. These commands, which are typically implemented over the RPC protocol on the DRSUAPI interface, are frequently utilized in Active Directory sync attacks to copy Active Directory information from domain controllers. Such activity, when not performed by new domain controllers to sync Active Directory contents, can indicate malicious domain or user enumeration, credential compromise or Active Directory enumeration.

Although the affected device made these requests to the previously noted domain controller, which was already compromised, such activity may have further enabled the compromise by allowing the threat actor to transfer these details to a more easily manageable device.

The device performing these DRSGetNCChanges requests would later be seen performing lateral movement activity and making connections to malicious endpoints.

Figure 3: Breach log highlighting the DRS operations performed by the corporate device to the destination domain controller. Such activity is rarely authorized for devices not tagged as administrative or as domain controllers.

Execution and Lateral Movement

At 23:09:53 UTC on April 30, 2023, the original domain server proceeded to make multiple uncommon WMI calls to a destination server on the same subnet (server01.corp.XXXX). Specifically, the device was observed making multiple RPC calls to IWbem endpoints on the server, which included login and ExecMethod (method execution) commands on the destination device. This destination device later proceeded to conduct additional beaconing activity to C2 endpoints and exfiltrate data.

Figure 4: Breach log for the domain controller performing WMI commands to the destination server during the lateral movement phase of the breach.

Similarly, beginning on May 1, 2023, at 00:11:09 UTC, the device desktop_02.corp.XXXX made multiple WMI requests to two additional devices, one server and one desktop, within the same subnet as the original domain controller. During this time, desktop_02.corp.XXXX  also utilized SMBv1, an outdated and typically non-compliant version communication protocol, to write the file rclone.exe to the same two destination devices. Rclone.exe, and its accompanying bat file, is a command-line tool developed by IT provider Rclone, to perform file management tasks. During this time, Darktrace also observed the device reading and deleting an unexpected numeric file on the ADMIN$ of the destination server, which may represent additional defense evasion techniques and tool staging.

Figure 5: Event log highlighting the writing of rclone.exe using the outdated SMBv1 communication protocol.
Figure 6: SMB logs indicating the reading and deletion of numeric string files on ADMIN$ shares of the destination devices during the time of the rclone.exe SMB writes. Such activity may be associated with tool staging and could indicate potential defense evasion techniques.

Given that the net loader sample analyzed by Symantec injects the backdoor into a WmiPrvSE.exe process, the use of WMI operations is not unexpected. Employment of WMI also correlates with the previously mentioned “living-off-the-land” tactics, as WMI services are commonly used for regular network and system administration purposes. Moreover, the staging of rclone.exe, a legitimate file management tool, for data exfiltration underscores attempts to blend into existing and expected network traffic and remain undetected on the customer’s network.

Data Exfiltration and Impact

Initial stages of data exfiltration actually began prior to some of the lateral movement events described above. On April 30, 2023, 23:09:47 the device server01.corp.XXXX, transferred nearly 11 GB of data to 173.44[.]141[.]47, as well as to the rare external IP address 170.130[.]55[.]77, which appears to have served as the main exfiltration destination during this compromise. Furthermore, the host made repeated connections to the same external IP associated with the initial suspicious beaconing activity (173.44[.]141[.]47) over SSL.

While the data exfiltration event unfolded, the device, server01.corp.XXXX, made multiple HTTP requests to 37.10[.]71[.]215, which featured URIs requesting the rclone.exe and rclone.bat files. This IP address was directly involved in the sample analyzed by Symantec. Furthermore, one of the devices that received the SMB file writes of rclone.exe and the WMI commands from desktop_02.corp.XXXX also performed SSL beaconing to endpoints associated with the compromise.

Between 01:20:45 - 03:31:41 UTC on May 1, 2023, a Darktrace detected a series of devices on the network performing a repeated pattern of activity, namely external connectivity followed by suspicious file downloads and external data transfer operations. Specifically, each affected device made multiple HTTP requests to 37.10[.]71[.]215 for rclone files. The devices proceeded to download the executable and/or binary files, and then transfer large amounts of data to the aforementioned endpoints, 170.130[.]55[.]77 and or 173-44-141-47[.]nip[.]io. Although the devices involved in data exfiltration utilized port 443 as a destination port, the connections actually used the SSH protocol. Darktrace recognized this behavior as unusual as port 443 is typically associated with the SSL protocol, while port 22 is reserved for SSH. Therefore, this activity may represent the threat actor’s attempts to remain undetected by security tools.

This unexpected use of SSH over port 443 also correlates with the descriptions of the new Sardonic backdoor according to threat researchers. Further beaconing and exfiltration activity was performed by an additional host one day later whereby the device made suspicious repeated connections to the aforementioned external hosts.

Figure 7: Connection details highlighting the use of port 443 for SSH connections during the exfiltration events.

In total, nine separate devices were involved in this pattern of activity. Five of these devices were labeled as ‘administrative’ devices according to their hostnames. Over the course of the entire exfiltration event, the attackers exfiltrated almost 61 GB of data from the organization’s environment.

Figure 8: Graph showing the levels of external data transfer from a breach device for one day on either side of the breach time. There is a large spike in such activity during the time of the breach that underscores the exfiltration events.

In addition to the individual anomaly detections by DETECT, Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the unusual behavior carried out by affected devices, connecting and collating multiple security events into one AI Analyst Incident. AI Analyst ensures that Darktrace can recognize and link the individual steps of a wider attack, rather than just identifying isolated incidents. While traditional security tools may mistake individual breaches as standalone activity, Darktrace’s AI allows it to provide unparalleled visibility over emerging attacks and their kill chains. Furthermore, Cyber AI Analyst’s instant autonomous investigations help to save customer security teams invaluable time in triaging incidents in comparison with human teams who would have to commit precious time and resources to conduct similar pattern analysis.

In this specific case, AI Analyst identified 44 separate security events from 18 different devices and was able to tie them together into one incident. The events that made up this AI Analyst Incident included:

  • Possible SSL Command and Control
  • Possible HTTP Command and Control
  • Unusual Repeated Connections
  • Suspicious Directory Replication ServiceActivity
  • Device / New or Uncommon WMI Activity
  • SMB Write of Suspicious File
  • Suspicious File Download
  • Unusual External Data Transfer
  • Unusual External Data Transfer to MultipleRelated Endpoints
Figure 9: Cyber AI Incident log highlighting multiple unusual anomalies and connecting them into one incident.

Had Darktrace RESPOND been enabled in autonomous response mode on the network of this prospective customer, it would have been able to take rapid mitigative action to block the malicious external connections used for C2 communication and subsequent data exfiltration, ideally halting the attack at this stage. As previously discussed, the limited network configuration of this trial customer meant that the encryption events unfortunately took place outside of Darktrace’s scope. When fully configured on a customer environment, Darktrace DETECT can identify such encryption attempts as soon as they occur. Darktrace RESPOND, in turn, would be able to immediately intervene by applying preventative actions like blocking internal connections that may represent file encryption, or limiting potentially compromised devices to a previously established pattern of life, ensuring they cannot carry out any suspicious activity.

Conclusion

Despite the limitations posed by the customer’s trial configuration, Darktrace demonstrated its ability to detect malicious activity associated with Syssphinx and track it across multiple stages of the kill chain.

Darktrace’s ability to identify the early stages of a compromise and various steps of the kill chain, highlights the necessity for machine learning-enabled, anomaly-based detection. In the face of threats such as Syssphinx, that exhibit the propensity to recast backdoor payloads and incorporate on “living-off-the-land” tactics, signatures and rules-based detection may not prove as effective. While Syssphinx and other threat groups will continue to adopt new tools, methods, and techniques, Darktrace’s Self-Learning AI is uniquely positioned to meet the challenge of such threats.

Appendix

DETECT Model Breaches Observed

•      Anomalous Server Activity / Anomalous External Activity from Critical Network Device

•      Anomalous Connection / Anomalous DRSGetNCChanges Operation

•      Device / New or Uncommon WMI Activity

•      Compliance / SMB Drive Write

•      Anomalous Connection / Data Sent to Rare Domain

•      Anomalous Connection / Uncommon 1 GiB Outbound

•      Unusual Activity / Unusual External Data Transfer

•      Unusual Activity / Unusual External Data to New Endpoints

•      Compliance / SSH to Rare External Destination

•      Anomalous Connection / Unusual SMB Version 1 Connectivity

•      Anomalous File / EXE from Rare External Location

•      Anomalous File / Script from Rare External Location

•      Compromise / Suspicious File and C2

•      Device / Initial Breach Chain Compromise

AI Analyst Incidents Observed

•      Possible SSL Command and Control

•      Possible HTTP Command and Control

•      Unusual Repeated Connections

•      Suspicious Directory Replication Service Activity

•      Device / New or Uncommon WMI Activity

•      SMB Write of Suspicious File

•      Suspicious File Download

•      Unusual External Data Transfer

•      Unusual External Data Transfer to Multiple Related Endpoints

IoCs

IoC - Type - Description

37.10[.]71[.]215 – IP – C2 + payload endpoint

173-44-141-47[.]nip[.]io – Hostname – C2 – payload

173.44[.]141[.]47 – IP – C2 + potential payload

170.130[.]55[.]77 – IP – Data exfiltration endpoint

Rclone.exe – Exe File – Common data tool

Rclone.bat – Script file – Common data tool

MITRE ATT&CK Mapping

Command and Control

T1071 - Application Layer Protocol

T1071.001 – Web protocols

T1573 – Encrypted channels

T1573.001 – Symmetric encryption

T1573.002 – Asymmetric encryption

T1571 – Non-standard port

T1105 – Ingress tool transfer

Execution

T1047 – Windows Management Instrumentation

Credential Access

T1003 – OS Credential Dumping

T1003.006 – DCSync

Lateral Movement

T1570 – Lateral Tool Transfer

T1021 - Remote Services

T1021.002 - SMB/Windows Admin Shares

T1021.006 – Windows Remote Management

Exfiltration

T1048 - Exfiltration Over Alternative Protocol

T1048.001 - Exfiltration Over Symmetric Encrypted Non-C2 Protocol

T1048.002 - Exfiltration Over Symmetric Encrypted Non-C2 Protocol

T1041 - Exfiltration Over C2 Channel

References

[1] https://cyberscoop.com/syssphinx-cybercrime-ransomware/

[2] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/Syssphinx-FIN8-backdoor

[3] https://www.bleepingcomputer.com/news/security/fin8-deploys-alphv-ransomware-using-sardonic-malware-variant/

[4] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/Syssphinx-FIN8-backdoor

[5] https://thehackernews.com/2023/07/fin8-group-using-modified-sardonic.html

[6] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/Syssphinx-FIN8-backdoor

[7] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/Syssphinx-FIN8-backdoor

[8] https://www.mandiant.com/resources/blog/windows-zero-day-payment-cards

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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Adam Potter
Senior Cyber Analyst
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February 18, 2025

Unifying IT & OT With AI-Led Investigations for Industrial Security

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As industrial environments modernize, IT and OT networks are converging to improve efficiency, but this connectivity also creates new attack paths. Previously isolated OT systems are now linked to IT and cloud assets, making them more accessible to attackers.

While organizations have traditionally relied on air gaps, firewalls, data diodes, and access controls to separate IT and OT, these measures alone aren’t enough. Threat actors often infiltrate IT/Enterprise networks first then exploit segmentation, compromising credentials, or shared IT/OT systems to move laterally, escalate privileges, and ultimately enter the OT network.

To defend against these threats, organizations must first ensure they have complete visibility across IT and OT environments.

Visibility: The first piece of the puzzle

Visibility is the foundation of effective industrial cybersecurity, but it’s only the first step. Without visibility across both IT and OT, security teams risk missing key alerts that indicate a threat targeting OT at their earliest stages.

For Attacks targeting OT, early stage exploits often originate in IT environments, adversaries perform internal reconnaissance among other tactics and procedures but then laterally move into OT first affecting IT devices, servers and workstations within the OT network. If visibility is limited, these threats go undetected. To stay ahead of attackers, organizations need full-spectrum visibility that connects IT and OT security, ensuring no early warning signs are missed.

However, visibility alone isn’t enough. More visibility also means more alerts, this doesn’t just make it harder to separate real threats from routine activity, but bogs down analysts who have to investigate all these alerts to determine their criticality.

Investigations: The real bottleneck

While visibility is essential, it also introduces a new challenge: Alert fatigue. Without the right tools, analysts are often occupied investigating alerts with little to no context, forcing them to manually piece together information and determine if an attack is unfolding. This slows response times and increases the risk of missing critical threats.

Figure 1: Example ICS attack scenario

With siloed visibility across IT and OT each of these events shown above would be individually alerted by a detection engine with little to no context nor correlation. Thus, an analyst would have to try to piece together these events manually. Traditional security tools struggle to keep pace with the sophistication of these threats, resulting in an alarming statistic: less than 10% of alerts are thoroughly vetted, leaving organizations vulnerable to undetected breaches. As a result, incidents inevitably follow.

Darktrace’s Cyber AI Analyst uses AI-led investigations to improve workflows for analysts by automatically correlating alerts wherever they occur across both IT and OT. The multi-layered AI engine identifies high-priority incidents, and provides analysts with clear, actionable insights, reducing noise and highlighting meaningful threats. The AI significantly alleviates workloads, enabling teams to respond faster and more effectively before an attack escalates.

Overcoming organizational challenges across IT and OT

Beyond technical challenges like visibility and alert management, organizational dynamics further complicate IT-OT security efforts. Fundamental differences in priorities, workflows, and risk perspectives create challenges that can lead to misalignment between teams:

Non-transferable practices: IT professionals might assume that cybersecurity practices from IT environments can be directly applied to OT environments. This can lead to issues, as OT systems and workflows may not handle IT security processes as expected. It's crucial to recognize and respect the unique requirements and constraints of OT environments.

Segmented responsibilities: IT and OT teams often operate under separate organizational structures, each with distinct priorities, goals, and workflows. While IT focuses on data security, network integrity, and enterprise applications, OT prioritizes uptime, reliability, and physical processes.

Different risk perspectives: While IT teams focus on preventing cyber threats and regulatory violations, OT teams prioritize uptime and operational reliability making them drawn towards asset inventory tools that provide no threat detection capability.

Result: A combination of disparate and ineffective tools and misaligned teams can make any progress toward risk reduction at an organization seem impossible. The right tools should be able to both free up time for collaboration and prompt better communication between IT and OT teams where it is needed. However, different size operations structure their IT and OT teams differently which impacts the priorities for each team.

In real-world scenarios, small IT teams struggle to manage security across both IT and OT, while larger organizations with OT security teams face alert fatigue and numerous false positives slowing down investigations and hindering effective communication with the IT security teams.

By unifying visibility and investigations, Darktrace / OT helps organizations of all sizes detect threats earlier, streamline workflows, and enhance security across both IT and OT environments. The following examples illustrate how AI-driven investigations can transform security operations, improving detection, investigation, and response.

Before and after AI-led investigation

Before: Small manufacturing company

At a small manufacturing company, a 1-3 person IT team juggles everything from email security to network troubleshooting. An analyst might see unusual traffic through the firewall:

  • Unusual repeated outbound traffic from an IP within their OT network destined to an unidentifiable external IP.

With no dedicated OT security tools and limited visibility into the industrial network, they don’t know what the internal device in question is, if it is beaconing to a malicious external IP, and what it may be doing to other devices within the OT network. Without a centralized dashboard, they must manually check logs, ask operators about changes, and hunt for anomalies across different systems.

After a day of investigation, they concluded the traffic was not to be expected activity. They stop production within their smaller OT network, update their firewall rules and factory reset all OT devices and systems within the blast radius of the IP device in question.

After: Faster, automated response with Cyber AI Analyst

With Darktrace / OT and Cyber AI Analyst, the IT team moves from reactive, manual investigations to proactive, automated threat detection:

  • Cyber AI Analyst connects alerts across their IT and OT infrastructure temporally mapping them to attack frameworks and provides contextual analysis of how alerts are linked, revealing in real time attackers attempting lateral movement from IT to OT.
  • A human-readable incident report explains the full scope of the incident, eliminating hours of manual investigation.
  • The team is faster to triage as they are led directly to prioritized high criticality alerts, now capable of responding immediately instead of wasting valuable time hunting for answers.

By reducing noise, providing context, and automating investigations, Cyber AI Analyst transforms OT security, enabling small IT teams to detect, understand, and respond to threats—without deep OT cybersecurity expertise.

Before: Large critical infrastructure organization

In large critical infrastructure operations, OT and IT teams work in separate silos. The OT security team needs to quickly assess and prioritize alerts, but their system floods them with notifications:

  • Multiple new device connected to the ICS network alerts
  • Multiple failed logins to HMI detected
  • Multiple Unusual Modbus/TCP commands detected
  • Repeated outbound OT traffic to IT destinations

At first glance, these alerts seem important, but without context, it’s unclear whether they indicate a routine error, a misconfiguration, or an active cyber-attack. They might ask:

  • Are the failed logins just a mistake, or a brute-force attempt?
  • Is the outbound traffic part of a scheduled update, or data exfiltration?

Without correlation across events, the engineer must manually investigate each one—checking logs, cross-referencing network activity, and contacting operators—wasting valuable time. Meanwhile, if it’s a coordinated attack, the adversary may already be disrupting operations.

After: A new workflow with Cyber AI Analyst

With Cyber AI Analyst, the OT security team gets clear, automated correlation of security events, making investigations faster and more efficient:

  • Automated correlation of OT threats: Instead of isolated alerts, Cyber AI Analyst stitches together related events, providing a single, high-confidence incident report that highlights key details.
  • Faster time to meaning: The system connects anomalous behaviors (e.g., failed logins, unusual traffic from an HMI, and unauthorized PLC modifications) into a cohesive narrative, eliminating hours of manual log analysis.
  • Prioritized and actionable alerts: OT security receives clear, ranked incidents, immediately highlighting what matters most.
  • Rapid threat understanding: Security teams know within minutes whether an event is a misconfiguration or a cyber-attack, allowing for faster containment.

With Cyber AI Analyst, large organizations cut through alert noise, accelerate investigations, and detect threats faster—without disrupting OT operations.

An AI-led approach to industrial cybersecurity

Security vendors with a primary focus on IT may lack insight into OT threats. Even OT-focused vendors have limited visibility into IT device exploitation within OT networks, leading to failed ability to detect early indicators of compromise. A comprehensive solution must account for the unique characteristics of various OT environments.

In a world where industrial security is no longer just about protecting OT but securing the entire digital-physical ecosystem as it interacts with the OT network, Darktrace / OT is an AI-driven solution that unifies visibility across IT, IoT and OT, Cloud into one cohesive defense strategy.

Whether an attack originates from an external breach, an insider threat, a supply chain compromise, in the Cloud, OT, or IT domains Cyber AI Analyst ensures that security teams see the full picture - before disruption occurs.

Learn more about Darktrace / OT 

  • Unify IT and OT security under a single platform, ensuring seamless communication and protection for all interconnected devices.
  • Maintain uptime with AI-driven threat containment, stopping attacks without disrupting production.
  • Mitigate risks with or without patches, leveraging MITRE mitigations to reduce attack opportunities.

Download the solution brief to see how Darktrace secures critical infrastructure.

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Daniel Simonds
Director of Operational Technology

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February 13, 2025

Why Darktrace / EMAIL excels against APTs

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What are APTs?

An Advanced Persistent Threat (APT) describes an adversary with sophisticated levels of expertise and significant resources, with the ability to carry out targeted cyber campaigns. These campaigns may penetrate an organization and remain undetected for long periods, allowing attackers to gather intelligence or cause damage over time.

Over the last few decades, the term APT has evolved from being almost exclusively associated with nation-state actors to a broader definition that includes highly skilled, well-resourced threat groups. While still distinct from mass, opportunistic cybercrime or "spray and pray" attacks, APT now refers to the elite tier of adversaries, whether state-sponsored or not, who demonstrate advanced capabilities, persistence, and a clear strategic focus. This shift reflects the growing sophistication of cyber threats, where non-state actors can now rival nation-states in executing covert, methodical intrusions to achieve long-term objectives.

These attacks are resource-intensive for threat actors to execute, but the potential rewards—ranging from financial gain to sensitive data theft—can be significant. In 2020, Business Email Compromise (BEC) attacks netted cybercriminals over $1.8 billion.1

And recently, the advent of AI has helped to automate launching these attacks, lowering the barriers to entry and making it more efficient to orchestrate the kind of attack that might previously have taken weeks to create. Research shows that AI can do 90% of a threat actor’s work2 – reducing time-to-target by automating tasks rapidly and avoiding errors in phishing communications. Email remains the most popular vector for initiating these sophisticated attacks, making it a critical battleground for cyber defense.

What makes APTs so successful?

The success of Advanced Persistent Threats (APTs) lies in their precision, persistence, and ability to exploit human and technical vulnerabilities. These attacks are carefully tailored to specific targets, using techniques like social engineering and spear phishing to gain initial access.

Once inside, attackers move laterally through networks, often remaining undetected for months or even years, silently gathering intelligence or preparing for a decisive strike. Alternatively, they might linger inside an account within the M365 environment, which could be even more valuable in terms of gathering information – in 2023 the average time to identify a breach in 2023 was 204 days.3

The subtle and long-term outlook nature of APTs makes them highly effective, as traditional security measures often fail to identify the subtle signs of compromise.

How Darktrace’s approach is designed to catch the most advanced threats

Luckily for our customers, Darktrace’s AI approach is uniquely equipped to detect and neutralize APTs. Unlike the majority of email security solutions that rely on static rules and signatures, or that train their AI on previous known-bad attack patterns, Darktrace leverages Self-Learning AI that baselines normal patterns of behavior within an organization, to immediately detect unusual activity that may signal an APT in progress.  

But in the modern era of email threats, no email security solution can guarantee 100% effectiveness. Because attackers operate with great sophistication, carefully adapting their tactics to evade detection – whether by altering attachments, leveraging compromised accounts, or moving laterally across an organization – a siloed security approach risks missing these subtle, multi-domain threats. That’s why a robust defense-in-depth strategy is essential to mitigate APTs.

Real-world threat finds: Darktrace / EMAIL in action

Let’s take a look at some real-world scenarios where Darktrace / EMAIL stopped tactics associated with APT campaigns in their tracks – from adversary-in-the-middle attacks to suspicious lateral movement.

1: How Darktrace disrupted an adversary-in-the-middle attack by identifying abnormal login redirects and blocking credential exfiltration

In October 2024, Darktrace detected an adversary-in-the-middle (AiTM) attack targeting a Darktrace customer. The attack began with a phishing email from a seemingly legitimate Dropbox address, which contained multiple link payloads inviting the recipient to access a file. Other solutions would have struggled to catch this attack, as the initial AitM attack was launched through delivering a malicious URL through a trusted vendor or service. Once compromised, the threat actor could have laid low on the target account, gathering reconnaissance, without detection from the email security solution.  

Darktrace / EMAIL identified the abnormal login redirects and flagged the suspicious activity. Darktrace / IDENTITY then detected unusual login patterns and blocked credential exfiltration attempts, effectively disrupting the attack and preventing the adversary from gaining unauthorized access. Read more.

Figure 1: Overview of the malicious email in the Darktrace / EMAIL console, highlighting Dropbox associated content/link payloads

2: How Darktrace stopped lateral movement to block NTLM hash theft

In early 2024, Darktrace detected an attack by the TA577 threat group, which aimed to steal NTLM hashes to gain unauthorized access to systems. The attack began with phishing emails containing ZIP files that connected to malicious infrastructure.  

A traditional email security solution would have likely missed this attack by focusing too heavily on analyzing the zip file payloads or relying on reputation analysis to understand whether the infrastructure was registered as bad before this activity was a recognized IoC.

Because it correlates activity across domains, Darktrace identified unusual lateral movement within the network and promptly blocked the attempts to steal NTLM hashes, effectively preventing the attackers from accessing sensitive credentials and securing the network. Read more.

Figure 2: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace / EMAIL

3: How Darktrace prevented the WarmCookie backdoor deployment embedded in phishing emails

In mid-2024, Darktrace identified a phishing campaign targeting organizations with emails impersonating recruitment firms. These emails contained malicious links that, when clicked, deployed the WarmCookie backdoor.  

These emails are difficult to detect, as they use social engineering tactics to manipulate users into engaging with emails and following the embedded malicious links – but if a security solution is not analysing content and context, these could be allowed through.

In several observed cases across customer environments, Darktrace detected and blocked the suspicious behavior associated with WarmCookie that had already managed to evade customers’ native email security. By using behavioral analysis to correlate anomalous activity across the digital estate, Darktrace was able to identify the backdoor malware strain and notify customers. Read more.

Conclusion

These threat examples highlight a key principle of the Darktrace approach – that a backwards-facing approach grounded in threat intelligence will always be one step behind.

Most threat actors operate in campaigns, carefully crafting attacks and testing them across multiple targets. Once a campaign is identified, good defenders and traditional security solutions quickly update their defenses with new threat intelligence, rules, and signatures. However, APTs have the resources to rapidly adapt – spinning up new infrastructure, modifying payloads and altering their attack footprint to evade detection.

This is where Darktrace / EMAIL excels. Only by analyzing each user, message and interaction can an email security solution hope to catch the types of highly-sophisticated attacks that have the potential to cause major reputational and financial damage. Darktrace / EMAIL ensures that even the most subtle threats are detected and blocked with autonomous response, before causing impact – helping organizations remain one step ahead of increasingly adaptive threat actors.

Download the Darktrace / EMAIL Solution Brief

Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.

  • Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
  • Experience 20-25% more threat blocking power with Darktrace / EMAIL
  • Stop the 58% of threats bypassing traditional email security

References

[1] FBI Internet Crime Report 2020

[2] https://www.optiv.com/insights/discover/blog/future-security-automation-how-ai-machine-learning-and-automation-are

[3] IBM Cost of a Data Breach Report 2023

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About the author
Carlos Gray
Product Manager
Your data. Our AI.
Elevate your network security with Darktrace AI