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April 1, 2023

Cyber Security Threats - Email Compromise With Generative AI

Discover how generative AI is impacting email attacks and what companies can do to prepare for more sophisticated and targeted attacker campaigns.
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
Max Heinemeyer
Global Field CISO
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01
Apr 2023

Email communications in the era of generative AI

Today’s headlines on cyber security attacks are dominated by serious breaches that cripple critical national infrastructure providers, wreak geopolitical havoc through nation state espionage, and create paralyzing financial demands through extortion and ransomware. But how do these breaches occur in the first place, and why do they keep happening?

Social engineering – specifically malicious cyber campaigns delivered via email - remain the primary source of an organization’s vulnerability to attack. A recent survey conducted by Darktrace to 6,700 global cross-industry professionals across the UK, US, Australia, France, Germany, and Netherlands, found almost a third (30%) have fallen victim to a fraudulent email. The risk, as ever, seems to be uncontrollably on the rise – 70% of respondents have noticed an increase in the frequency of malicious emails in the last six months. 

At the end of last year, I wrote about how widespread accessibility to generative AI has compounded the problem, leading to likely efficiency gains for skilled threat actors launching email attacks. Just a few weeks ago, we published research which demonstrated that while the number of email attacks across our own customer base has remained steady since ChatGPT’s release, those that rely on tricking victims into clicking malicious links have declined, while linguistic complexity, including text volume, punctuation, and sentence length among others, have increased. This indicates that cyber-criminals may be redirecting their focus to crafting more sophisticated social engineering scams that exploit user trust delivered over email. 

Our latest findings, conducted by Darktrace Research, today reveal a 135% increase in ‘novel social engineering attacks’ across thousands of active Darktrace/Email customers from January to February 2023, corresponding with the widespread adoption of ChatGPT. A novel social engineering phishing email is an email attack that shows a strong linguistic deviation – semantically and syntactically – compared to other phishing emails. The trend suggests that generative AI, such as ChatGPT, is providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale.

Organizations are already well aware of the danger novel threats pose – globally, 82% of respondents reported are concerned that hackers can use generative AI to create scam emails that are indistinguishable from genuine communication.

Navigating the trust deficit 

Employees are being exploited continuously through their primary means of communication - email. Given that humans, and our psychology, are at the heart of the problem, organizations have scrambled to develop awareness and training programs that are delivered routinely to employees in an attempt to help them defend themselves and their organization. While a defense-in-depth approach is generally a good practice to follow, the value of security awareness training, teaching employees to spot attempts at social engineering delivered in text format, is diminishing rapidly. This problem has become especially evident now that we find ourselves in a world where ‘bad’ emails look all but undistinguishable to the human eye from ‘good’ emails. 

Over emphasizing the responsibility of employees poses a business challenge as well as a security problem: a bloated trust deficit. In times of economic uncertainty, business success is predicated on employee productivity, creativity, and efficiency. All three of these are squashed when employees treat the communication they receive, both internal and external, with forensic suspicion and mistrust. 

As generative AI becomes more mainstream – across images, audio, video, and text – we anticipate that this erosion of trust in digital communication will only continue. What happens to the workplace if an employee is left questioning their own perception when communicating with their manager or a colleague, who they can see and hear over a video conference call, but who may be an entirely fictitious creation?

The way forward

The future lies in a partnership between artificial intelligence and human beings where the algorithms are responsible for determining whether communication is malicious or benign, thereby taking the burden of responsibility off the human. In turn, humans can pursue activities that drive productivity and performance. Current training and awareness programs, coupled with traditional email security technologies which assume that knowledge of past attacks will help predict campaigns, are not sustainable in this rapidly evolving landscape. 

Our research reveals that traditional email security tools that rely on knowledge of past threats, take an average of thirteen days from an attack being launched on a victim to that attack being detected. This leaves defenders vulnerable for almost two weeks if they rely solely on traditional tools. When this statistic is contextualized against the 135% increase we’ve seen in novel social engineering campaigns, the inefficiency of ‘attack centric’ email security is made perfectly evident. If we don’t know how to define entirely new and unique attacks, how can we ever hope to recognize them based on past attacks? 

A deep understanding of ‘you’ is needed in the face of these radical changes to the email threat landscape. Instead of trying to predict attacks, an understanding of your employees’ behavior, based from their email inbox, is needed to create patterns of life for every email user: their relationships, tone and sentiments and hundreds of other data points. By leveraging AI to combat email security threats, we not only reduce risk, but revitalize organizational trusts and contribute to business outcomes.

Ironically, generative AI may be worsening the social engineering challenge, but AI that knows you, could be the parry. 

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
Max Heinemeyer
Global Field CISO

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November 26, 2025

CastleLoader & CastleRAT: Behind TAG150’s Modular Malware Delivery System

CastleLoader & CastleRAT: Behind TAG150’s Modular Malware Delivery SystemDefault blog imageDefault blog image

What is TAG-150?

TAG-150, a relatively new Malware-as-a-Service (MaaS) operator, has been active since March 2025, demonstrating rapid development and an expansive, evolving infrastructure designed to support its malicious operations. The group employs two custom malware families, CastleLoader and CastleRAT, to compromise target systems, with a primary focus on the United States [1]. TAG-150’s infrastructure included numerous victim-facing components, such as IP addresses and domains functioning as command-and-control (C2) servers associated with malware families like SecTopRAT and WarmCookie, in addition to CastleLoader and CastleRAT [2].

As of May 2025, CastleLoader alone had infected a reported 469 devices, underscoring the scale and sophistication of TAG-150’s campaign [1].

What are CastleLoader and CastleRAT?

CastleLoader is a loader malware, primarily designed to download and install additional malware, enabling chain infections across compromised systems [3]. TAG-150 employs a technique known as ClickFix, which uses deceptive domains that mimic document verification systems or browser update notifications to trick victims into executing malicious scripts. Furthermore, CastleLoader leverages fake GitHub repositories that impersonate legitimate tools as a distribution method, luring unsuspecting users into downloading and installing malware on their devices [4].

CastleRAT, meanwhile, is a remote access trojan (RAT) that serves as one of the primary payloads delivered by CastleLoader. Once deployed, CastleRAT grants attackers extensive control over the compromised system, enabling capabilities such as keylogging, screen capturing, and remote shell access.

TAG-150 leverages CastleLoader as its initial delivery mechanism, with CastleRAT acting as the main payload. This two-stage attack strategy enhances the resilience and effectiveness of their operations by separating the initial infection vector from the final payload deployment.

How are they deployed?

Castleloader uses code-obfuscation methods such as dead-code insertion and packing to hinder both static and dynamic analysis. After the payload is unpacked, it connects to its command-and-control server to retrieve and running additional, targeted components.

Its modular architecture enables it to function both as a delivery mechanism and a staging utility, allowing threat actors to decouple the initial infection from payload deployment. CastleLoader typically delivers its payloads as Portable Executables (PEs) containing embedded shellcode. This shellcode activates the loader’s core module, which then connects to the C2 server to retrieve and execute the next-stage malware.[6]

Following this, attackers deploy the ClickFix technique, impersonating legitimate software distribution platforms like Google Meet or browser update notifications. These deceptive sites trick victims into copying and executing PowerShell commands, thereby initiating the infection kill chain. [1]

When a user clicks on a spoofed Cloudflare “Verification Stepprompt, a background request is sent to a PHP script on the distribution domain (e.g., /s.php?an=0). The server’s response is then automatically copied to the user’s clipboard using the ‘unsecuredCopyToClipboard()’ function. [7].

The Python-based variant of CastleRAT, known as “PyNightShade,” has been engineered with stealth in mind, showing minimal detection across antivirus platforms [2]. As illustrated in Figure 1, PyNightShade communicates with the geolocation API service ip-api[.]com, demonstrating both request and response behavior

Packet Capture (PCAP) of PyNightShade, the Python-based variant of CastleRAT, communicating with the geolocation API service ip-api[.]com.
Figure 1: Packet Capture (PCAP) of PyNightShade, the Python-based variant of CastleRAT, communicating with the geolocation API service ip-api[.]com.

Darktrace Coverage

In mid-2025, Darktrace observed a range of anomalous activities across its customer base that appeared linked to CastleLoader, including the example below from a US based organization.

The activity began on June 26, when a device on the customer’s network was observed connecting to the IP address 173.44.141[.]89, a previously unseen IP for this network along with the use of multiple user agents, which was also rare for the user.  It was later determined that the IP address was a known indicator of compromise (IoC) associated with TAG-150’s CastleRAT and CastleLoader operations [2][5].

Figure 2: Darktrace’s detection of a device making unusual connections to the malicious endpoint 173.44.141[.]89.

The device was observed downloading two scripts from this endpoint, namely ‘/service/download/data_5x.bin’ and ‘/service/download/data_6x.bin’, which have both been linked to CastleLoader infections by open-source intelligence (OSINT) [8]. The archives contains embedded shellcode, which enables attackers to execute arbitrary code directly in memory, bypassing disk writes and making detection by endpoint detection and response (EDR) tools significantly more difficult [2].

 Darktrace’s detection of two scripts from the malicious endpoint.
Figure 3: Darktrace’s detection of two scripts from the malicious endpoint.

In addition to this, the affected device exhibited a high volume of internal connections to a broad range of endpoints, indicating potential scanning activity. Such behavior is often associated with reconnaissance efforts aimed at mapping internal infrastructure.

Darktrace / NETWORK correlated these behaviors and generated an Enhanced Monitoring model, a high-fidelity security model designed to detect activity consistent with the early stages of an attack. These high-priority models are continuously monitored and triaged by Darktrace’s Security Operations Center (SOC) as part of the Managed Threat Detection and Managed Detection & Response services, ensuring that subscribed customers are promptly alerted to emerging threats.

Darktrace detected an unusual ZIP file download alongside the anomalous script, followed by internal connectivity. This activity was correlated under an Enhanced Monitoring model.
Figure 4: Darktrace detected an unusual ZIP file download alongside the anomalous script, followed by internal connectivity. This activity was correlated under an Enhanced Monitoring model.

Darktrace Autonomous Response

Fortunately, Darktrace’s Autonomous Response capability was fully configured, enabling it to take immediate action against the offending device by blocking any further connections external to the malicious endpoint, 173.44.141[.]89. Additionally, Darktrace enforced a ‘group pattern of life’ on the device, restricting its behavior to match other devices in its peer group, ensuring it could not deviate from expected activity, while also blocking connections over 443, shutting down any unwanted internal scanning.

Figure 5: Actions performed by Darktrace’s Autonomous Response to contain the ongoing attack.

Conclusion

The rise of the MaaS ecosystem, coupled with attackers’ growing ability to customize tools and techniques for specific targets, is making intrusion prevention increasingly challenging for security teams. Many threat actors now leverage modular toolkits, dynamic infrastructure, and tailored payloads to evade static defenses and exploit even minor visibility gaps. In this instance, Darktrace demonstrated its capability to counter these evolving tactics by identifying early-stage attack chain behaviors such as network scanning and the initial infection attempt. Autonomous Response then blocked the CastleLoader IP delivering the malicious ZIP payload, halting the attack before escalation and protecting the organization from a potentially damaging multi-stage compromise

Credit to Ahmed Gardezi (Cyber Analyst) Tyler Rhea (Senior Cyber Analyst)
Edited by Ryan Traill (Analyst Content Lead)

Appendices

Darktrace Model Detections

  • Anomalous Connection / Unusual Internal Connections
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous File / Script from Rare External Location
  • Initial Attack Chain Activity (Enhanced Monitoring Model)

MITRE ATT&CK Mapping

  • T15588.001 - Resource Development – Malware
  • TG1599 – Defence Evasion – Network Boundary Bridging
  • T1046 – Discovery – Network Service Scanning
  • T1189 – Initial Access

List of IoCs
IoC - Type - Description + Confidence

  • 173.44.141[.]89 – IP – CastleLoader C2 Infrastructure
  • 173.44.141[.]89/service/download/data_5x.bin – URI – CastleLoader Script
  • 173.44.141[.]89/service/download/data_6x.bin – URI  - CastleLoader Script
  • wsc.zip – ZIP file – Possible Payload

References

[1] - https://blog.polyswarm.io/castleloader

[2] - https://www.recordedfuture.com/research/from-castleloader-to-castlerat-tag-150-advances-operations

[3] - https://www.pcrisk.com/removal-guides/34160-castleloader-malware

[4] - https://www.scworld.com/brief/malware-loader-castleloader-targets-devices-via-fake-github-clickfix-phishing

[5] https://www.virustotal.com/gui/ip-address/173.44.141.89/community

[6] https://thehackernews.com/2025/07/castleloader-malware-infects-469.html

[7] https://www.cryptika.com/new-castleloader-attack-using-cloudflare-themed-clickfix-technique-to-infect-windows-computers/

[8] https://www.cryptika.com/castlebot-malware-as-a-service-deploys-range-of-payloads-linked-to-ransomware-attacks/

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November 20, 2025

Managing OT Remote Access with Zero Trust Control & AI Driven Detection

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The shift toward IT-OT convergence

Recently, industrial environments have become more connected and dependent on external collaboration. As a result, truly air-gapped OT systems have become less of a reality, especially when working with OEM-managed assets, legacy equipment requiring remote diagnostics, or third-party integrators who routinely connect in.

This convergence, whether it’s driven by digital transformation mandates or operational efficiency goals, are making OT environments more connected, more automated, and more intertwined with IT systems. While this convergence opens new possibilities, it also exposes the environment to risks that traditional OT architectures were never designed to withstand.

The modernization gap and why visibility alone isn’t enough

The push toward modernization has introduced new technology into industrial environments, creating convergence between IT and OT environments, and resulting in a lack of visibility. However, regaining that visibility is just a starting point. Visibility only tells you what is connected, not how access should be governed. And this is where the divide between IT and OT becomes unavoidable.

Security strategies that work well in IT often fall short in OT, where even small missteps can lead to environmental risk, safety incidents, or costly disruptions. Add in mounting regulatory pressure to enforce secure access, enforce segmentation, and demonstrate accountability, and it becomes clear: visibility alone is no longer sufficient. What industrial environments need now is precision. They need control. And they need to implement both without interrupting operations. All this requires identity-based access controls, real-time session oversight, and continuous behavioral detection.

The risk of unmonitored remote access

This risk becomes most evident during critical moments, such as when an OEM needs urgent access to troubleshoot a malfunctioning asset.

Under that time pressure, access is often provisioned quickly with minimal verification, bypassing established processes. Once inside, there’s little to no real-time oversight of user actions whether they’re executing commands, changing configurations, or moving laterally across the network. These actions typically go unlogged or unnoticed until something breaks. At that point, teams are stuck piecing together fragmented logs or post-incident forensics, with no clear line of accountability.  

In environments where uptime is critical and safety is non-negotiable, this level of uncertainty simply isn’t sustainable.

The visibility gap: Who’s doing what, and when?

The fundamental issue we encounter is the disconnect between who has access and what they are doing with it.  

Traditional access management tools may validate credentials and restrict entry points, but they rarely provide real-time visibility into in-session activity. Even fewer can distinguish between expected vendor behavior and subtle signs of compromise, misuse or misconfiguration.  

As a result, OT and security teams are often left blind to the most critical part of the puzzle, intent and behavior.

Closing the gaps with zero trust controls and AI‑driven detection

Managing remote access in OT is no longer just about granting a connection, it’s about enforcing strict access parameters while continuously monitoring for abnormal behavior. This requires a two-pronged approach: precision access control, and intelligent, real-time detection.

Zero Trust access controls provide the foundation. By enforcing identity-based, just-in-time permissions, OT environments can ensure that vendors and remote users only access the systems they’re explicitly authorized to interact with, and only for the time they need. These controls should be granular enough to limit access down to specific devices, commands, or functions. By applying these principles consistently across the Purdue Model, organizations can eliminate reliance on catch-all VPN tunnels, jump servers, and brittle firewall exceptions that expose the environment to excess risk.

Access control is only one part of the equation

Darktrace / OT complements zero trust controls with continuous, AI-driven behavioral detection. Rather than relying on static rules or pre-defined signatures, Darktrace uses Self-Learning AI to build a live, evolving understanding of what’s “normal” in the environment, across every device, protocol, and user. This enables real-time detection of subtle misconfigurations, credential misuse, or lateral movement as they happen, not after the fact.

By correlating user identity and session activity with behavioral analytics, Darktrace gives organizations the full picture: who accessed which system, what actions they performed, how those actions compared to historical norms, and whether any deviations occurred. It eliminates guesswork around remote access sessions and replaces it with clear, contextual insight.

Importantly, Darktrace distinguishes between operational noise and true cyber-relevant anomalies. Unlike other tools that lump everything, from CVE alerts to routine activity, into a single stream, Darktrace separates legitimate remote access behavior from potential misuse or abuse. This means organizations can both audit access from a compliance standpoint and be confident that if a session is ever exploited, the misuse will be surfaced as a high-fidelity, cyber-relevant alert. This approach serves as a compensating control, ensuring that even if access is overextended or misused, the behavior is still visible and actionable.

If a session deviates from learned baselines, such as an unusual command sequence, new lateral movement path, or activity outside of scheduled hours, Darktrace can flag it immediately. These insights can be used to trigger manual investigation or automated enforcement actions, such as access revocation or session isolation, depending on policy.

This layered approach enables real-time decision-making, supports uninterrupted operations, and delivers complete accountability for all remote activity, without slowing down critical work or disrupting industrial workflows.

Where Zero Trust Access Meets AI‑Driven Oversight:

  • Granular Access Enforcement: Role-based, just-in-time access that aligns with Zero Trust principles and meets compliance expectations.
  • Context-Enriched Threat Detection: Self-Learning AI detects anomalous OT behavior in real time and ties threats to access events and user activity.
  • Automated Session Oversight: Behavioral anomalies can trigger alerting or automated controls, reducing time-to-contain while preserving uptime.
  • Full Visibility Across Purdue Layers: Correlated data connects remote access events with device-level behavior, spanning IT and OT layers.
  • Scalable, Passive Monitoring: Passive behavioral learning enables coverage across legacy systems and air-gapped environments, no signatures, agents, or intrusive scans required.

Complete security without compromise

We no longer have to choose between operational agility and security control, or between visibility and simplicity. A Zero Trust approach, reinforced by real-time AI detection, enables secure remote access that is both permission-aware and behavior-aware, tailored to the realities of industrial operations and scalable across diverse environments.

Because when it comes to protecting critical infrastructure, access without detection is a risk and detection without access control is incomplete.

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About the author
Pallavi Singh
Product Marketing Manager, OT Security & Compliance
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