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October 24, 2024

Phishing and Persistence: Darktrace’s Role in Defending Against a Sophisticated Account Takeover

In a recent incident, Darktrace uncovered a M365 account takeover attempt targeting a company in the manufacturing industry. The attacker executed a sophisticated phishing attack, gaining access through the organization’s SaaS platform. This allowed the threat actor to create a new inbox rule, potentially setting the stage for future compromises.
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
Vivek Rajan
Cyber Analyst
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24
Oct 2024

The exploitation of SaaS platforms

As businesses continue to grow and evolve, the need for sharing ideas through productivity and cloud Software-as-a-Service (SaaS) platforms is becoming increasingly crucial. However, these platforms have also become prime targets for cyber attackers.

Threat actors often exploit these widely-used services to gain unauthorized access, steal sensitive information, and disrupt business operations. The growing reliance on SaaS platforms makes them attractive entry points for cybercriminals, who use sophisticated techniques such as phishing, social engineering, and malware to compromise these systems.

Services like Microsoft 365 are regularly targeted by threat actors looking for an entry point into an organization’s environment to carry out malicious activities. Securing these platforms is crucial to protect business data and ensure operational continuity.

Darktrace / EMAIL detection of the phishing attack

In a recent case, Darktrace observed a customer in the manufacturing sector receiving a phishing email that led to a threat actor logging in and creating an email rule. Threat actors often create email rules to move emails to their inbox, avoiding detection. Additionally, Darktrace detected a spoofed domain registered by the threat actor. Despite already having access to the customer’s SaaS account, the actor seemingly registered this domain to maintain persistence on the network, allowing them to communicate with the spoofed domain and conduct further malicious activity.

Darktrace / EMAIL can help prevent compromises like this one by blocking suspicious emails as soon as they are identified. Darktrace’s AI-driven email detection and response recognizes anomalies that might indicate phishing attempts and applies mitigative actions autonomously to prevent the escalation of an attack.

Unfortunately, in this case, Darktrace was not configured in Autonomous Response mode at the time of the attack, meaning actions had to be manually applied by the customer’s security team. Had it been fully enabled, it would have held the emails, preventing them from reaching the intended recipient and stopping the attack at its inception.

However, Darktrace’s Managed Threat Detection alerted the Security Operations Center (SOC) team to the compromise, enabling them to thoroughly investigate the incident and notify the customer before further damage could occur.

The Managed Threat Detection service continuously monitors customer networks for suspicious activities that may indicate an emerging threat. When such activities are detected, alerts are sent to Darktrace’s expert Cyber Analysts for triage, significantly speeding up the remediation process.

Attack Overview

On May 2, 2024, Darktrace detected a threat actor targeting a customer in the manufacturing sector then an unusual login to their SaaS environment was observed prior to the creation of a new email rule.

Darktrace immediately identified the login as suspicious due to the rarity of the source IP (31.222.254[.]27) and ASN, coupled with the absence of multi-factor authentication (MFA), which was typically required for this account.

The new email rule was intended to mark emails as read and moved to the ‘Conversation History’ folder for inbound emails from a specific domain. The rule was named “….,,,”, likely the attacker attempting to setup their new rule with an unnoteworthy name to ensure it would not be noticed by the account’s legitimate owner. Likewise, by moving emails from a specific domain to ‘Conversation History’, a folder that is rarely used by most users, any phishing emails sent by that domain would remain undetected by the user.

Darktrace’s detection of the unusual SaaS login and subsequent creation of the new email rule “….,,,”.
Figure 1: Darktrace’s detection of the unusual SaaS login and subsequent creation of the new email rule “….,,,”.

The domain in question was identified as being newly registered and an example of a typosquat domain. Typosquatting involves registering new domains with intentional misspelling designed to convince users to visit fake, and often malicious, websites. This technique is often used in phishing campaigns to create a sense of legitimacy and trust and deceive users into providing sensitive information. In this case, the suspicious domain closely resembled several of the customer’s internal domains, indicating an attempt to impersonate the organization’s legitimate internal sites to gain the target’s trust. Furthermore, the creation of this lookalike domain suggests that the attack was highly targeted at this specific customer.

Interestingly, the threat actor registered this spoofed domain despite already having account access. This was likely intended to ensure persistence on the network without having to launch additional phishing attacks. Such use of spoofed domain could allow an attacker to maintain a foothold in their target network and escalate their malicious activities without having to regain access to the account. This persistence can be used for various purposes, including data exfiltration, spreading malware, or launching further attacks.

Following this, Darktrace detected a highly anomalous email being sent to the customer’s account from the same location as the initial unusual SaaS login. Darktrace’s anomaly-based detection is able to identify threats that human security teams and traditional signature-based methods might miss. By analyzing the expected behavior of network users, Darktrace can recognize the subtle deviations from the norm that may indicate malicious activity. Unfortunately, in this instance, without Darktrace’s Autonomous Response capability enabled, the phishing email was able to successfully reach the recipient. While Darktrace / EMAIL did suggest that the email should be held from the recipients inbox, the customer was required to manually approve it.

Despite this, the Darktrace SOC team were still able to support the customer as they were subscribed to the Managed Threat Detection service. Following the detection of the highlight anomalous activity surrounding this compromise, namely the unusual SaaS login followed by a new email rule, an alert was sent to the Darktrace SOC for immediate triage, who then contacted the customer directly urging immediate action.

Conclusion

This case underscores the need to secure SaaS platforms like Microsoft 365 against sophisticated cyber threats. As businesses increasingly rely on these platforms, they become prime targets for attackers seeking unauthorized access and disruption.

Darktrace’s anomaly-based detection and response capabilities are crucial in identifying and mitigating such threats. In this instance, Darktrace detected a phishing email that led to a threat actor logging in and creating a suspicious email rule. The actor also registered a spoofed domain to maintain persistence on the network.

Darktrace / EMAIL, with its AI-driven detection and analysis, can block suspicious emails before they reach the intended recipient, preventing attacks at their inception. Meanwhile, Darktrace’s SOC team promptly investigated the activity and alerted the customer to the compromise, enabling them to take immediate action to remediate the issue and prevent any further damage.

Credit to Vivek Rajan (Cyber Security Analyst) and Ryan Traill (Threat Content Lead).

Appendices

Darktrace Model Detections

  • SaaS / Access / Unusual External Source for SaaS Credential Use
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active
  • SaaS / Resource / Unusual Access to Delegated Resource by Non Owner
  • SaaS / Email Nexus / Unusual Login Location Following Sender Spoof
  • Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Unusual Login and New Email Rule

Indicators of Compromise (IoCs)

IoC - Type - Description + Confidence

31.222.254[.]27 – IP -  Suspicious Login Endpoint

MITRE ATT&CK Mapping

Tactic – Technqiue – Sub-technique of (if applicable)

Cloud Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078.004 - T1078

Cloud Service Dashboard – DISCOVERY - T1538

Compromise Accounts - RESOURCE DEVELOPMENT - T1586

Steal Web Session Cookie - CREDENTIAL ACCESS - T1539

Outlook Rules – PERSISTENCE - T1137.005 - T1137

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
Vivek Rajan
Cyber Analyst

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May 21, 2026

Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches

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How enterprise AI Agents are changing the risk landscape  

Generative AI Agents are changing the way work gets done inside enterprises, and subsequently how security risks may emerge. Organizations have quickly realized that providing these agents with wider access to tooling, internal information, and granting permissions for the agent to perform autonomous actions can greatly increase the efficiency of employee workflows.

Early deployments of Generative AI systems led many organizations to scope individual components as self-contained applications: a chat interface, a model, and a prompt, with guardrails placed at the boundary. Research from Gartner has shown that while the volume and scope of Agentic AI deployments in enterprise environments is rapidly accelerating, many of the mechanisms required to manage risk, trust, and cost are still maturing.

The issue now resides on whether an agent can be influenced, misdirected, or manipulated in ways that leads to unsafe behavior across a broader system.

Why prompt security matters in enterprise AI

Prompt security matters in enterprise AI because prompts are the primary way users and systems interact with Agentic AI models, making them one of the earliest and most visible indicators of how these systems are being used and where risk may emerge.

For security teams, prompt monitoring is a logical starting point for understanding enterprise AI usage, providing insight into what types of questions are being asked and tasks are being given to AI Agents, how these systems are being guided, and whether interactions align with expected behavior. Complete prompt security takes this one step further, filtering out or blocking sensitive or dangerous content to prevent risks like prompt injection and data leakage.

However, visibility only at the prompt layer can create a false sense of security. Prompts show what was asked, but not always why it was asked, or what downstream actions were triggered by the agent across connected systems, data sources, or applications.

What prompt security reveals  

The primary function of prompt security is to minimize risks associated with generative and agentic AI use, but monitoring and analysis of prompts can also grant insight into use cases for particular agents and model. With comprehensive prompt security, security teams should be able to answer the following questions for each prompt:

  • What task was the user attempting to complete?
  • What data was included in the request, and was any of the data high-risk or confidential?
  • Was the interaction high-risk, potentially malicious, or in violation of company policy?
  • Was the prompt anomalous (in comparison to previous prompts sent to the agent / model)?

Improving visibility at this layer is a necessary first step, allowing organizations to establish a baseline for how AI systems are being used and where potential risks may exist.  

Prompt security alone does not provide a complete view of risk. Further data is needed to understand how the prompt is interpreted, how context is applied, what autonomous actions the agent takes (if any), or what downstream systems are affected. Understanding the outcome of a query is just as important for complete prompt security as understanding the input prompt itself – for example, a perfectly normal, low-risk prompt may inadvertently result in an agent taking a high-risk action.

Comprehensive AI security systems like Darktrace / SECURE AI can monitor and analyze both the prompt submitted to a Generative AI system, as well as the responses and chain-of-thought of the system, providing greater insight into the behavior of the system. Darktrace / SECURE AI builds on the core Darktrace methodology, learning the expected behaviors of your organization and identifying deviations from the expected pattern of life.

How organizations address prompt security today

As prompt-level visibility has become a focus, a range of approaches have emerged to make this activity more observable and controllable. Various monitoring and logging tools aim to capture prompt inputs to be analyzed after the fact.  

Input validation and filtering systems attempt to intervene earlier, inspecting prompts before they reach the model. These controls look for known jailbreak patterns, language indicative of adversarial attacks, or ambiguous instructions which could push the system off course.

Importantly, for a prompt security solution to be accurate and effective, prompts must be continually observed and governed, rather than treated as a point-in-time snapshot.  

Where prompt security breaks down in real environments

In more complex environments, especially those involving multiple agents or extensive tool use, AI security becomes harder to define and control.

Agent-to-Agent communications can be harder to monitor and trace as these happen without direct user interaction. Communication between agents can create routes for potential context leakage between agents, unintentional privilege escalation, or even data leakage from a higher privileged agent to a lower privileged one.

Risk is shaped not just by what is asked, but by the conditions in which that prompt operates and the actions an agent takes. Controls at the orchestration layer are starting to reflect this reality. Techniques such as context isolation, scoped memory, and role-based boundaries aim to limit how far a prompt’s influence can extend.  

Furthermore, Shadow AI usage can be difficult to monitor. AI systems that are deployed outside of formal governance structures and Generative AI systems hosted on unknown endpoints can fly under the radar and can go unseen by monitoring tools, leaving a critical opening where adversarial prompts may go undetected. Darktrace / SECURE AI features comprehensive detection of Shadow AI usage, helping organizations identify potential risk areas.

How prompt security fits in a broader AI risk model

Prompt security is an important starting point, but it is not a complete security strategy. As AI systems become more integrated into enterprise environments, the risks extend to what resources the system can access, how it interprets context, and what actions it is allowed to take across connected tools and workflows.

This creates a gap between visibility and control. Prompt security alone allows security teams to observe prompt activity but falls short of creating a clear understanding of how that activity translates into real-world impact across the organization.

Closing that gap requires a broader approach, one that connects signals across human and AI agent identities, SaaS, cloud, and endpoint environments. It means understanding not just how an AI system is being used, but how that usage interacts with the rest of the digital estate.

Prompt security, in that sense, is less of a standalone solution and more of an entry point into a larger problem: securing AI across the enterprise as a whole.

Explore how Darktrace / SECURE AI brings prompt security to enterprises

Darktrace brings more than a decade of AI expertise, built on an enterprise‑wide platform designed to operate in and understand the behaviors of the complex, ambiguous environments where today’s AI now lives. With Darktrace / SECURE AI, enterprises can safely adopt, manage, monitor, and build AI within their business.  

Learn about Darktrace / SECURE AI here.

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Jamie Bali
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May 21, 2026

Data Center Security: Improving Visibility and Threat Detection Across IT, OT, and IoT

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What is data center cybersecurity?

Much of the conversation surrounding the data center boom has focused on power generation, cooling efficiency and water resources, construction, and compute capacity. In addition, cybersecurity has quietly become one of the most critical operational concerns as modern data centers are becoming some of the most operationally complex networked environments.

The more connected data center environments become, the larger and more dynamic their attack surface grows. What makes data center security particularly challenging is that they no longer resemble traditional enterprise IT environments alone. Instead, they operate like critical infrastructure facilities

Challenges of securing data centers

What makes these environments complicated is that the technologies responsible for keeping them operational: power distribution, cooling systems, airflow management, environmental controls, surveillance, and physical access management, all rely heavily on Operational Technology (OT), Industrial IoT (IIoT), and IoT systems alongside traditional IT infrastructure.

Programmable logic controllers (PLCs), building management systems (BMS), energy management systems (EMS), surveillance cameras, access control platforms, virtualization infrastructure, engineering workstations, contractor laptops, and cloud-connected orchestration systems now coexist within the same environment. Many are connected through routable networks, managed remotely, and accessed by 3rd party OEMs or System Integrators.

Why modern data center infrastructure faces increasing cyber risk

The challenge is not simply that there are more devices. It is that these IT, OT and IOT systems and devices are now deeply interconnected in ways that blur the boundaries between operational and enterprise infrastructure.

OT systems responsible for cooling and power distribution communicate alongside enterprise IT infrastructure. IoT devices used for physical security sit adjacent to cloud-connected management platforms. Third-party vendors and contractors frequently require remote access to maintain operations and optimize performance. AI-driven automation platforms increasingly orchestrate workflows across multiple environments simultaneously.

Every additional connection improves efficiency and scalability, but every additional connection also creates new relationships between systems that adversaries may exploit.

How IT, OT, and IoT convergence expands the data center attack surface

Historically in critical infrastructure environments enterprise IT, and OT or industrial control systems ICS, have been often separated by a DMZ.

That separation has steadily disappeared in pursuit of efficiency and access to valuable data that lives within the OT networks such as how many widgets were produced today. This conceptually is commonly referred to as “IT OT convergence.”

Modern data centers increasingly depend on interconnected systems operating across multiple domains simultaneously and face a similar reality when it comes to IT OT convergence.  

This convergence creates efficiency and visibility benefits, but it also introduces structural security challenges that traditional approaches struggle to address.

Many of the OT systems were never originally designed with modern cybersecurity requirements in mind. OT devices often prioritize uptime and operational continuity over security controls. IoT and OT devices may have limited security hardening, are inconsistently patched, or insecure default configurations. Third-party connectivity introduces external dependencies that organizations do not fully control.

As environments converge the attack surface changes and grows, attackers may exploit weaker systems positioned adjacent to critical operations for initial access. For example, a compromised IoT device may provide access into broader infrastructure, or an exposed remote management interface may enable lateral movement into OT systems.  

For defenders, rather than forcing segmentation where it’s not possible, focus oversight and monitoring across interconnected systems and how this activity might create operational risk, gaining visibility across these systems will ensure better awareness of and protection across the cracks in your systems attackers look to exploit.

Why traditional data center security tools create visibility gaps

Many organizations still secure IT, OT, and IoT environments through separate tools, teams, and workflows. Historically, this made sense. The environments themselves were more isolated, and the operational priorities were different.

But convergence changes the nature of detection and response.

Modern attacks increasingly move across domains as lateral movement and discovery techniques are pervasive amongst all the most well-known attacks to have disrupted OT. Adversaries may gain access through phishing or credential compromise, establish persistence in IT systems, pivot into operational infrastructure, exploit unmanaged IoT devices, and move laterally across cloud-connected environments.

Viewed independently, many of these signals may appear low priority or disconnected.

An anomalous login attempt, unusual device communication, changes in network traffic patterns, or abnormal behavior from an industrial controller may not appear significant on their own. The problem emerges when these activities are part of a broader attack chain unfolding across multiple systems simultaneously.

Siloed security models struggle to correlate this activity effectively because they lack shared operational context. Security teams may see isolated indicators while missing the relationships between them.

This creates a fundamental visibility problem that has discursive effects across security teams, leading to analyst overload, tedious alert investigations, and slower response times.

The issue is not simply detecting threats faster. It is understanding how activity across IT, OT, IoT, cloud, and remote access systems relate to one another in real time before operational disruption occurs.

Security measures to safeguard modern data center infrastructure

Rule-based systems, predefined indicators, and signature-driven approaches remain useful for identifying known threats, but they are less effective at identifying subtle behavioral deviations, novel attack paths, insider activity, 3rd party supply chain exploitation or attacks that move across operational domains.  

Darktrace’s Self-Learning AI approach is designed to operate across converged IT, OT, IoT, and cloud environments. Using multiple layers of AI models, Darktrace solutions come together to achieve behavioral prediction, real-time threat detection and response, and incident investigation, all while empowering your security team with visibility and control.

Because the models are environment-specific, they can adapt across highly diverse infrastructure including operational technology, physical security systems, enterprise IT, cloud workloads, and third-party connectivity.

This enables organizations to build a more unified understanding of activity across the data center.

Unified visibility across interconnected environments

Darktrace provides visibility across IT, OT, IoT, and cloud systems through a centralized platform. Security teams and data center operators can maintain live asset inventories, monitor data flows, identify vulnerable or end-of-life systems, and better understand how interconnected infrastructure communicates across the environment.

This becomes increasingly important in environments where unmanaged devices, transient contractor systems, and third-party connectivity continuously alter operational conditions.

Threat detection, investigation, and response

Darktrace applies multiple AI models to identify anomalous activity that may indicate known threats, novel attacks, insider activity, or cross-domain compromise.

By understanding how devices and systems normally behave within the environment, Darktrace can identify subtle deviations that may otherwise remain undetected in siloed environments.

Its autonomous response capabilities can also help contain threats during their early stages before they escalate into operational disruption. Meanwhile, Cyber AI Analyst provides explainable AI-driven investigations that help security teams understand the relationships between events, systems, and users involved in potential incidents.

Proactive risk identification

As data center environments continue to evolve, organizations increasingly need to understand not only active threats, but also where structural weaknesses may exist across interconnected systems.

Through capabilities such as attack path modeling and behavioral risk analysis, Darktrace helps organizations prioritize remediation efforts and identify areas where operational exposure may increase over time.

This supports a more proactive security posture in environments where operational continuity is critical.

Securing the future of interconnected infrastructure

As data centers continue to scale in size, complexity, and operational importance, their reliance on interconnected IT, OT, IoT, cloud, and AI-driven systems will only deepen.

The challenge organizations face is no longer simply protecting individual devices or isolated environments. It is understanding how risk emerges across interconnected systems operating together and detecting threats to these systems in real time.

This is ultimately what makes modern data center security different from traditional enterprise security models. The operational dependencies are broader, the environments are more heterogeneous, and the consequences of disruption and intent of adversaries are more like those in the critical infrastructure space.

Securing these environments therefore requires more than fragmented visibility across disconnected tools. Organizations increasingly need unified approaches capable of understanding relationships across systems, detecting threats early, and responding before operational disruption spreads across critical infrastructure.

As the infrastructure powering the digital economy continues to evolve, cybersecurity resilience will become increasingly inseparable from operational resilience itself.

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Daniel Simonds
Director of Operational Technology
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