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April 10, 2023

Detecting Malicious Email Activity & AI Impersonating

Discover how two different phishing attempts from some known and unknown senders used a payroll diversion and credential sealing box link to harm users.
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
Isabelle Cheong
Cyber Security Analyst
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10
Apr 2023

Social engineering has become widespread in the cyber threat landscape in recent years, and the near-universal use of social media today has allowed attackers to research and target victims more effectively. Social engineering involves manipulating users to carry out actions such as revealing sensitive information like login credentials or credit card details. It can also lead to user account compromises, causing huge disruption to an organization’s digital estate. 

As people use social media platforms not only for personal reasons, but also for business purposes, attackers gain information they can exploit in social engineering attacks. For example, a threat actor may attempt to impersonate a known individual or legitimate service to take advantage of a user’s established trust. This is a highly successful method of social engineering because mimicking known contacts makes it difficult for traditional security tools that rely on deny-lists to detect the attack.

In October 2022, Darktrace identified and responded to two separate malicious email campaigns in which threat actors attempted to impersonate known contacts in an effort to compromise customer devices. As it learns the normal behavior of every user in the email system, Darktrace was able to instantly detect these threats and mitigate them autonomously, preventing significant disruption to the customer networks.

Payroll Diversion Fraud Attempt Impersonating a Former Employee 

While a customer in the Canadian energy sector was trialing Darktrace in October 2022, Darktrace/Email™ identified a suspicious email seemingly sent from an employee within the organization. The email was sent to the Senior Director of Human Resources (HR) with a subject line of “Change in payroll Direct Deposit.” The email requested a change in bank account information for an employee. However, Darktrace recognized that the sender was using a free mail address that contained random letters, indicating it may have been algorithmically generated. Since this incident occurred during a trial, Darktrace/Email was not configured to take action. Otherwise, it would have prevented the email from landing in the inbox. In this case though, the email went through, bypassing all other security tools in place.

Although the email was from an unknown sender, the HR director believed the email could have been legitimate as the employee who appeared to be the sender had left the organization seven days prior and no longer had access to their corporate email account. However, after reviewing it in the Darktrace/Email dashboard, the customer grew suspicious and contacted the former employee directly to verify if the request was legitimate. The former employee validated the suspicions by confirming they had sent no such email.

Further investigation by the customer revealed that the former employee had been vocal about their departure on various social media platforms. This gave threat actors valuable information to believably impersonate the former employee and defraud the organization. 

Such attempts to target organizations’ HR departments and divert payroll are common tactics for cyber-criminals and are often identified by Darktrace/Email across the customer base. Darktrace/Email is able to instantly identify the indicators associated with these spoofing attempts and immediately bring them to the attention of the customer’s security team. 

Using Legitimate File Sharing Service to Share a Phishing Link 

On October 7, 2022, a customer in the Singaporean construction sector was targeted by a phishing campaign attempting to impersonate a law firm known to the organization. Almost 200 employees received an email with the subject line “Accepted: Valuation Agreement.” 

Figure 1: Sample of an UI view of the message held showing anomaly indicators, history, association, and validation.

Four days earlier, Darktrace observed communication between another email address associated with the law firm and an employee of the customer. Darktrace/Email noted that it was the first time this correspondent had sent emails to the customer. 

Figure 2: Metrics showing how well the sender’s domain is known within the digital environment.

The emails contained a highly unusual link to a file sharing service, (hxxps://ssvilvensstokes[.]app[.]box[.]com/notes), hidden behind the text “PREVIEW OR PRINT COPY OF DOCUMENT HERE.” Darktrace analysts investigated this event further and found that around 30 similar URLs had been identified as suspicious using OSINT security tools in October 2022, suggesting the customer was not the only target of this phishing campaign.

Figure 3: Preview of the phishing email’s body.
Figure 4: Darktrace’s evaluation of the link contained in the phishing email.

Additional OSINT work revealed that the link directed to a website which appeared to host a PDF file named “Valuation Agreement.” The recipient would then be prompted to follow another link (hulking-citrine-krypton[.]glitch[.]me), again hidden behind the text “OPEN OR ACCESS DOCUMENT HERE” to view the file. Subsequently, the user would be prompted to enter their Microsoft 365 credentials. 

Figure 5: The page displayed when the phishing link was clicked, viewed in a sandbox environment.
Figure 6: Example of a page shown when recipient clicks the second link, accessing “hulking-citrine-krypton[.]glitch[.]me”. 

This page contained the text “This document has been scanned for viruses by Norton Antivirus Security.” This is another example of threat actors’ employing social engineering techniques by impersonating well-known brands, such as established security vendors, to gain the trust of users and increase their likelihood of success.

It is highly probable that a real employee of the law firm had their account hijacked and that a malicious actor was exploiting it to send out these phishing emails en masse as part of a supply chain attack. In such cases, malicious actors rely on their targets’ trust of known contacts to not question departures from their normal conversations. 

Darktrace was able to instantly detect multiple anomalies in these emails, despite the fact that they were seemingly sent by known correspondents. The activity detected automatically triggered model breaches associated with unexpected and visually prominent links. As a result, Darktrace/Email responded by locking the link, stopping users from being able to click it.

Darktrace subsequently identified additional emails from this sender attempting to target other recipients within the company, triggering the model breaches associated with a surge in email sending indicative of a phishing campaign. In response, Darktrace/Email autonomously acted and filed these emails as junk. As more emails were detected across the customer’s environment, the anomaly score of the sender increased and Darktrace ultimately held back over 160 malicious emails, safeguarding recipients from potential account compromise.           

The following Darktrace/Email models were breached throughout the course of this phishing campaign:

  • Unusual/Sender Surge 
  • Unusual/Undisclosed Recipients 
  • Antigena Anomaly 
  • Association/Unlikely Recipient Association 
  • Link/Low Link Association 
  • Link/Visually Prominent Link 
  • Link/Visually Prominent Link Unexpected For Sender 
  • Unusual/New Sender Wide Distribution
  • Unusual/Undisclosed Recipients + New Address Known Domain

Conclusion

Social engineering plays a role in many of the major threats challenging current email cyber security, as attackers can use it to manipulate users into transferring money, revealing credentials, clicking malicious links, and more. 

The above threat stories happened before language generating AI became mainstream with the release of ChatGPT in December 2022. Now, it is even easier for malicious actors to generate sophisticated social engineering emails. By using social media posts as input, social engineering emails written by generative AI can be highly targeted and produced at scale. They often avoid the flags users are trained to look for, like poor grammar and spelling mistakes, and can hide payloads or forgo them entirely.

To mitigate the risk of possible social engineering attempts, it is recommended that organizations implement social media policies that advise employees to be cautious of what they post online and enact procedures to verify if fund transfer requests are legitimate.

Yet these policies are not enough on their own. Darktrace/Email can identify suspicious email traits, whether an email is sent from a known correspondent or an unknown sender. With Self-Learning AI, it knows an organization’s users better than any impersonator could. In this way, Darktrace/Email detects anomalies within emails and neutralizes malicious components at machine-speed, stopping attacks at their earliest stages, before employees fall victim. 

Appendices

List of Indicators of Compromise (IoCs)

Domain:

hxxps://ssvilvensstokes[.]app[.]box[.]com/notes/*?s=* - 1st external link (seen in email)

hxxps://hulking-citrine-krypton[.]glitch[.]me/flk.html - 2nd external link, masked behind “OPEN OR ACCESS DOCUMENT HERE”

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
Isabelle Cheong
Cyber Security Analyst

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July 21, 2025

Global Telecom Provider: Powering and Protecting the World's Data Giants

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This global leader plays a critical role in keeping the world connected. The company works with some of the largest and most influential public and private organizations in the world to enable ultra-fast data transmission.

Safeguarding the systems that keep the world connected

Standing at the forefront of global connectivity, this industry leader designs and manages large-scale communications systems that power the world’s most data-intensive enterprises – including social media giants, hyperscale cloud providers, and major data center operators. Given the scale, confidentiality, and sensitivity of the systems and data it helps transport, the company faces complex cybersecurity challenges.

Protecting sensitive customer data

Most of the organization’s projects are custom-designed and highly proprietary, making data privacy and Intellectual Property (IP) protection critical to maintaining trust and confidentiality with customers. In an industry where every competitor knows the landscape intimately, any loss of data could cause significant damage.

International security implications

The company faces a broad range of advanced cyber threats – from corporate espionage and supply chain risks to cyber-physical attacks on critical infrastructure. Its international footprint adds complexity, including cross-border regulatory compliance. A successful attack could disrupt business, compromise IP, or trigger wider consequences like disruptions to international data transfers and other critical services.

The global leader works closely with communities to anticipate threats that could impact the global communications network at large.

In this environment, cybersecurity is a foundation for international trust,” said the organization’s CISO.

Building a resilient cybersecurity strategy from the ground up

The CISO had the rare opportunity to build the IT and cybersecurity infrastructure from scratch. "Initially, we bought what everyone else buys,” referencing the traditional mix of firewalls, routers, and antivirus tools. “But I knew we needed to do more.”

Self-Learning AI – “the missing piece”

With solid perimeter defenses in place, the security team sought deeper protection inside the network. Darktrace’s Self-Learning AI stood out. “Unlike other solutions, Darktrace’s AI looks beyond known threat signatures, learning what’s normal for our environment and flagging what’s not. That was the missing piece – something that could help us even when everything else failed.”

A solution and partnership that delivered

The CISO said he appreciated the ability to observe Darktrace in action before full deployment, noting that the Darktrace team was there every step of the way, providing guidance and expertise to ensure he got the most out of his investment.

Partnership was especially valuable given the company’s explosive 400% growth over the last six years. As resources were stretched and priorities shifted, “Darktrace remained patient and responsive. We’re slow and methodical, but the Darktrace support team was phenomenal, never losing momentum and earning our trust.”

A unified cybersecurity ecosystem

Today, the global leader is using the Darktrace ActiveAI Security Platform™ as a core part of its layered defense strategy, including:

The CISO appreciates how, as a unified cybersecurity platform, Darktrace has an intuitive user interface, which makes it easier for his team to investigate alerts visually, even without deep technical expertise.

Advancing defenses while impacting the bottom line

A 24/7 “safety net”

The fact that this company has never been hacked is the clearest proof it made the right decision with Darktrace, said the CISO. Initially rolled out in Human Confirmation Mode, meaning it would not take autonomous action without explicit approval from the security team, Darktrace immediately uncovered threats and anomalies that other tools had missed.

Darktrace acts as a must-have safety net—ready to step in when other tools fall short,” said the CISO.

From monitoring internal behavior and identifying unusual attack patterns, to autonomously neutralizing threats after hours, the platform provides peace of mind in a high-stakes industry. “Darktrace is my dark horse – the thing I have in my back pocket if everything else fails. It’s here to save the day, save my company, and maybe even save my career.”

Autonomous capabilities free up time for skilled analysts

Darktrace’s AI-powered detection and response capabilities are deeply embedded in the team’s day-to-day operations, autonomously investigating and responding to the majority of potential threats. Cyber AI Analyst conducted a total of 2,776 total investigations within three months, averaging just 12 minutes to autonomously investigate an incident. Of those 2,776 investigations, Darktrace resolved 2,671 (96%) autonomously and escalated only 105 (4%) to analysts. Darktrace has dramatically reduced alert fatigue and freed up analysts to focus on what really matters, saving the security team 486 analyst hours on investigations within a 20-day period.

From noise to actionable insight

Darktrace delivers meaningful data and meaningful alerts. “If Darktrace escalates an incident, we drop everything and work on that. We trust in Darktrace.” When analysts do need to investigate an incident, Darktrace’s forensic logs and guided remediation suggestions have slashed the time analysts spend on investigations by four to five times.

Stronger security. Lower cost.

The CISO says, “Darktrace is a money-saver for our organization, making continued investments an easy sell to the CEO and the board.”  When he found himself down a resource after a member of the security team left the organization, the CISO turned to Darktrace Managed Threat Detection and Response services for 24/7 expert support. “It was a no brainer. We got better coverage, higher skill levels, and around-the-clock support – all for less than what we would pay to employ a single analyst.”

Scaling securely into the future

Securing networks in motion  

The organization is preparing to scale both its operations and security posture across existing distributed, mobile and deployable communications networks that historically have been disconnected. Some of these networks are in constant motion and operating in some of the world’s most volatile regions. “Darktrace will act as an autonomous defender, monitoring for anomalous behavior and intervening, when necessary, especially during those dangerous times when an asset ‘goes dark’ and becomes disconnected from the broader network,” said the CISO.

Applying AI strategically

As the organization continues to evaluate where and how to apply AI, its emphasis will be on technologies that can act independently to contain threats – especially in environments where human response may be delayed. “It’s about using the right kind of AI for the right challenge. That’s why we’re investing in Darktrace, with tools that can adapt and learn even in isolation and provide real-time protection wherever we operate.”

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July 17, 2025

Introducing the AI Maturity Model for Cybersecurity

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AI adoption in cybersecurity: Beyond the hype

Security operations today face a paradox. On one hand, artificial intelligence (AI) promises sweeping transformation from automating routine tasks to augmenting threat detection and response. On the other hand, security leaders are under immense pressure to separate meaningful innovation from vendor hype.

To help CISOs and security teams navigate this landscape, we’ve developed the most in-depth and actionable AI Maturity Model in the industry. Built in collaboration with AI and cybersecurity experts, this framework provides a structured path to understanding, measuring, and advancing AI adoption across the security lifecycle.

Overview of AI maturity levels in cybersecurity

Why a maturity model? And why now?

In our conversations and research with security leaders, a recurring theme has emerged:

There’s no shortage of AI solutions, but there is a shortage of clarity and understanding of AI uses cases.

In fact, Gartner estimates that “by 2027, over 40% of Agentic AI projects will be canceled due to escalating costs, unclear business value, or inadequate risk controls. Teams are experimenting, but many aren’t seeing meaningful outcomes. The need for a standardized way to evaluate progress and make informed investments has never been greater.

That’s why we created the AI Security Maturity Model, a strategic framework that:

  • Defines five clear levels of AI maturity, from manual processes (L0) to full AI Delegation (L4)
  • Delineating the outcomes derived between Agentic GenAI and Specialized AI Agent Systems
  • Applies across core functions such as risk management, threat detection, alert triage, and incident response
  • Links AI maturity to real-world outcomes like reduced risk, improved efficiency, and scalable operations

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How is maturity assessed in this model?

The AI Maturity Model for Cybersecurity is grounded in operational insights from nearly 10,000 global deployments of Darktrace's Self-Learning AI and Cyber AI Analyst. Rather than relying on abstract theory or vendor benchmarks, the model reflects what security teams are actually doing, where AI is being adopted, how it's being used, and what outcomes it’s delivering.

This real-world foundation allows the model to offer a practical, experience-based view of AI maturity. It helps teams assess their current state and identify realistic next steps based on how organizations like theirs are evolving.

Why Darktrace?

AI has been central to Darktrace’s mission since its inception in 2013, not just as a feature, but the foundation. With over a decade of experience building and deploying AI in real-world security environments, we’ve learned where it works, where it doesn’t, and how to get the most value from it. This model reflects that insight, helping security leaders find the right path forward for their people, processes, and tools

Security teams today are asking big, important questions:

  • What should we actually use AI for?
  • How are other teams using it — and what’s working?
  • What are vendors offering, and what’s just hype?
  • Will AI ever replace people in the SOC?

These questions are valid, and they’re not always easy to answer. That’s why we created this model: to help security leaders move past buzzwords and build a clear, realistic plan for applying AI across the SOC.

The structure: From experimentation to autonomy

The model outlines five levels of maturity :

L0 – Manual Operations: Processes are mostly manual with limited automation of some tasks.

L1 – Automation Rules: Manually maintained or externally-sourced automation rules and logic are used wherever possible.

L2 – AI Assistance: AI assists research but is not trusted to make good decisions. This includes GenAI agents requiring manual oversight for errors.

L3 – AI Collaboration: Specialized cybersecurity AI agent systems  with business technology context are trusted with specific tasks and decisions. GenAI has limited uses where errors are acceptable.

L4 – AI Delegation: Specialized AI agent systems with far wider business operations and impact context perform most cybersecurity tasks and decisions independently, with only high-level oversight needed.

Each level reflects a shift, not only in technology, but in people and processes. As AI matures, analysts evolve from executors to strategic overseers.

Strategic benefits for security leaders

The maturity model isn’t just about technology adoption it’s about aligning AI investments with measurable operational outcomes. Here’s what it enables:

SOC fatigue is real, and AI can help

Most teams still struggle with alert volume, investigation delays, and reactive processes. AI adoption is inconsistent and often siloed. When integrated well, AI can make a meaningful difference in making security teams more effective

GenAI is error prone, requiring strong human oversight

While there is a lot of hype around GenAI agentic systems, teams will need to account for inaccuracy and hallucination in Agentic GenAI systems.

AI’s real value lies in progression

The biggest gains don’t come from isolated use cases, but from integrating AI across the lifecycle, from preparation through detection to containment and recovery.

Trust and oversight are key initially but evolves in later levels

Early-stage adoption keeps humans fully in control. By L3 and L4, AI systems act independently within defined bounds, freeing humans for strategic oversight.

People’s roles shift meaningfully

As AI matures, analyst roles consolidate and elevate from labor intensive task execution to high-value decision-making, focusing on critical, high business impact activities, improving processes and AI governance.

Outcome, not hype, defines maturity

AI maturity isn’t about tech presence, it’s about measurable impact on risk reduction, response time, and operational resilience.

[related-resource]

Outcomes across the AI Security Maturity Model

The Security Organization experiences an evolution of cybersecurity outcomes as teams progress from manual operations to AI delegation. Each level represents a step-change in efficiency, accuracy, and strategic value.

L0 – Manual Operations

At this stage, analysts manually handle triage, investigation, patching, and reporting manually using basic, non-automated tools. The result is reactive, labor-intensive operations where most alerts go uninvestigated and risk management remains inconsistent.

L1 – Automation Rules

At this stage, analysts manage rule-based automation tools like SOAR and XDR, which offer some efficiency gains but still require constant tuning. Operations remain constrained by human bandwidth and predefined workflows.

L2 – AI Assistance

At this stage, AI assists with research, summarization, and triage, reducing analyst workload but requiring close oversight due to potential errors. Detection improves, but trust in autonomous decision-making remains limited.

L3 – AI Collaboration

At this stage, AI performs full investigations and recommends actions, while analysts focus on high-risk decisions and refining detection strategies. Purpose-built agentic AI systems with business context are trusted with specific tasks, improving precision and prioritization.

L4 – AI Delegation

At this stage, Specialized AI Agent Systems performs most security tasks independently at machine speed, while human teams provide high-level strategic oversight. This means the highest time and effort commitment activities by the human security team is focused on proactive activities while AI handles routine cybersecurity tasks

Specialized AI Agent Systems operate with deep business context including impact context to drive fast, effective decisions.

Join the webinar

Get a look at the minds shaping this model by joining our upcoming webinar using this link. We’ll walk through real use cases, share lessons learned from the field, and show how security teams are navigating the path to operational AI safely, strategically, and successfully.

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About the author
Ashanka Iddya
Senior Director, Product Marketing
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