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April 20, 2022

Email Compromise To Mass Phishing Campaign

Read Darktrace's in-depth analysis on the shift from business email compromise to mass phishing campaigns. Gain the knowledge to safeguard your business.
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
Shuh Chin Goh
Written by
Sam Lister
SOC Analyst
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20
Apr 2022

It is common for attackers to send large volumes of malicious emails from the email accounts which they compromise. Before carrying out this mass-mailing activity, there are predictable, preparatory steps which attackers take, such as registering mass-mailing applications and creating new inbox rules. In this blog, we will provide details of an attack observed in February 2022 in which a threat actor conducted a successful mass-mailing attack at a financial company based in Africa.

Attack summary

In February 2022, an attacker attempted to infiltrate the email environment of a financial services company based in Africa. At the beginning of February, the attacker likely gained a foothold in the company’s email environment by tricking an internal user into entering the credentials of their corporate email account into a phishing page. Over the following week, the attacker used the compromised account credentials to conduct a variety of activities, such as registering a mass-mailing application and creating a new inbox rule.

After taking these preparatory steps, the attacker went on to send out large volumes of phishing emails from the internal user’s email account. The attacker consequently obtained the credentials of several further internal corporate accounts. They used the credentials of one of these accounts to carry out similar preparatory steps (registering a mass-mailing application and creating a new inbox rule). After taking these steps, the attacker again sent large volumes of phishing emails from the account. At this point, the customer requested assistance from Darktrace’s SOC to aid investigation, and the intrusion was consequently contained by the company.

Since the attacker carried out their activities using a VPN and an Amazon cloud service, the endpoints from which the activities took place did not serve as particularly helpful indicators of an attack. However, prior to sending out phishing emails from internal users’ accounts, the attacker did carry out other predictable, preparatory activities. One of the main goals of this blog is to highlight that these behaviors serve as valuable signs of preparation for mass-mailing activity.

Attack timeline

Figure 1: Timeline of the intrusion

On February 3, the attacker sent a phishing email to the corporate account of an employee. The email was sent from the corporate account of an employee at a company with business ties to the victim enterprise. It is likely that the attacker had compromised this account prior to sending the phishing email from it. The phishing email in question claimed to be an overdue payment reminder. Within the email, there was a link hidden behind the display text “view invoice”. The hostname of the phishing link’s URL was a subdomain of questionpro[.]eu — an online survey platform. The page referred to by the URL was a fake Microsoft Outlook login page.

Figure 2: Destination of phishing link within the email sent by the attacker

Antigena Email, Darktrace’s email security solution, identified the highly unusual linguistic structure of the email, given its understanding of ‘normal’ for that sender. This was reflected in an inducement shift score of 100. However, in this case, the original URL of the phishing link was rewritten by Mimecast’s URL protection service in a way which made the full URL impossible to extract. Consequently, Antigena Email did not know what the original URL of the link was. Since the link was rewritten by Mimecast’s URL protection service, the email’s recipient will have received a warning notification in their browser upon clicking the link. It seems that the recipient ignored the warning, and consequently divulged their email account credentials to the attacker.

For Antigena Email to hold an email from a user’s mailbox, it must judge with high confidence that the email is malicious. In cases where the email contains no suspicious attachments or links, it is difficult for Antigena Email to obtain such high degrees of confidence, unless the email displays clear payload-independent malicious indicators, such as indicators of spoofing or indicators of extortion. In this case, the email, as seen by Antigena Email, didn’t contain any suspicious links or attachments (since Mimecast had rewritten the suspicious link) and the email didn’t contain any indicators of spoofing or extortion.

Figure 3: The email’s high inducement shift score highlights that the email’s linguistic content and structure were unusual for the email’s sender

Shortly after receiving the email, the internal user’s corporate device was observed making SSL connections to the questionpro[.]eu phishing endpoint. It is likely that the user divulged their email account credentials during these connections.

Figure 4: The above screenshot — obtained from Advanced Search — depicts the connections made by the account owner’s device on February 3

Between February 3 and February 7, the attacker logged into the user’s email account several times. Since these logins were carried out using a common VPN service, they were not identified as particularly unusual by Darktrace. However, during their login sessions, the attacker exhibited behavior which was highly unusual for the email account’s owner. The attacker was observed creating an inbox rule called “ _ ” on the user’s email account,[1] as well as registering and granting permissions to a mass-mailing application called Newsletter Software SuperMailer. These steps were taken by the attacker in preparation for their subsequent mass-mailing activity.

On February 7, the attacker sent out phishing emails from the user’s account. The emails were sent to hundreds of internal and external mailboxes. The email claimed to be an overdue payment reminder and it contained a questionpro[.]eu link hidden behind the display text “view invoice”. It is likely that the inbox rule created by the attacker caused all responses to this phishing email to be deleted. Attackers regularly create inbox rules on the email accounts which they compromise to ensure that responses to the malicious emails which they distribute are hidden from the accounts’ owners.[2]

Since Antigena Email does not have visibility of internal-to-internal emails, the phishing email was delivered fully weaponized to hundreds of internal mailboxes. On February 7, after the phishing email was sent from the compromised internal account, more than twenty internal devices were observed making SSL connections to the relevant questionpro[.]eu endpoint, indicating that many internal users had clicked the phishing link and possibly revealed their account credentials to the attacker.

Figure 5: The above screenshot — obtained from Advanced Search — depicts the large volume of connections made by internal devices to the phishing endpoint

Over the next five days, the attacker was observed logging into the corporate email accounts of at least six internal users. These logins were carried out from the same VPN endpoints as the attacker’s original logins. On February 11, the attacker was observed creating an inbox rule named “ , ” on one of these accounts. Shortly after, the attacker went on to register and grant permissions to the same mass-mailing application, Newsletter Software SuperMailer. As with the other account, these steps were taken by the attacker in preparation for subsequent mass-mailing activity.

Figure 6: The above screenshot — obtained from Advanced Search — outlines all of the actions involving the mass-mailing application that were taken by the attacker (accounts have been redacted)

On February 11, shortly after 08:30 (UTC), the attacker widely distributed a phishing email from this second user’s account. The phishing email was distributed to hundreds of internal and external mailboxes. Unlike the other phishing emails used by the attacker, this one claimed to be a purchase order notification, and it contained an HTML file named PurchaseOrder.html. Within this file, there was a link to a suspicious page on the public relations (PR) news site, everything-pr[.]com. After the phishing email was sent from the compromised internal account, more than twenty internal devices were observed making SSL connections to the relevant everything-pr[.]com endpoint, indicating that many internal users had opened the malicious attachment.

Figure 7: The above screenshot — obtained from Advanced Search — depicts the connections made by internal devices to the endpoint referenced in the malicious attachment

On February 11, the customer submitted an Ask the Expert (ATE) request to Darktrace’s SOC team. The guidance provided by the SOC helped the security team to contain the intrusion. The attacker managed to maintain a presence within the organization’s email environment for eight days. During these eight days, the attacker sent out large volumes of phishing emails from two corporate accounts. Before sending out these phishing emails, the attacker carried out predictable, preparatory actions. These actions included registering a mass-mailing application with Azure AD and creating an inbox rule.

Darktrace guidance

There are many learning points for this particular intrusion. First, it is important to be mindful of signs of preparation for malicious mass-mailing activity. After an attacker compromises an email account, there are several actions which they will likely perform before they send out large volumes of malicious emails. For example, they may create an inbox rule on the account, and they may register a mass-mailing application with Azure AD. The Darktrace models SaaS / Compliance / New Email Rule and SaaS / Admin / OAuth Permission Grant are designed to pick up on these behaviors.

Second, in cases where an attacker succeeds in sending out phishing emails from an internal, corporate account, it is advised that customers make use of Darktrace’s Advanced Search to identify users that may have divulged account credentials to the attacker. The phishing email sent from the compromised account will likely contain a suspicious link. Once the hostname of the link has been identified, it is possible to ask Advanced Search to display all HTTP or SSL connections to the host in question. If the hostname is www.example.com, you can get Advanced Search to display all SSL connections to the host by using the Advanced Search query, @fields.server_name:"www.example.com", and you can get Advanced Search to display all HTTP connections to the host by using the query, @fields.host:"www.example.com".

Third, it is advised that customers make use of Darktrace’s ‘watched domains’ feature[3] in cases where an attacker succeeds in sending out malicious emails from the accounts they compromise. If a hostname is added to the watched domains list, then a model named Compromise / Watched Domain will breach whenever an internal device is observed connecting to it. If Antigena Network is configured, then observed attempts to connect to the relevant host will be blocked if the hostname is added to the watched domains list with the ‘flag for Antigena’ toggle switched on. If an attacker succeeds in sending out a malicious email from an internal, corporate account, it is advised that customers add hostnames of phishing links within the email to the watched domains list and enable the Antigena flag. Doing so will cause Darktrace to identify and thwart any attempts to connect to the relevant phishing endpoints.

Figure 8: The above screenshot — obtained from the Model Editor — shows that Antigena Network prevented ten internal devices from connecting to phishing endpoints after the relevant phishing hostnames were added to the watched domains list on February 11

For Darktrace customers who want to find out more about phishing detection, refer here for an exclusive supplement to this blog.

MITRE ATT&CK techniques observed

Thanks to Paul Jennings for his contributions.

Footnotes

1. https://docs.microsoft.com/en-us/powershell/module/exchange/new-inboxrule?view=exchange-ps

2. https://www.fireeye.com/current-threats/threat-intelligence-reports/rpt-fin4.html

3. https://customerportal.darktrace.com/product-guides/main/watched-domains

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
Shuh Chin Goh
Written by
Sam Lister
SOC Analyst

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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.

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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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July 17, 2025

Forensics or Fauxrensics: Five Core Capabilities for Cloud Forensics and Incident Response

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The speed and scale at which new cloud resources can be spun up has resulted in uncontrolled deployments, misconfigurations, and security risks. It has had security teams racing to secure their business’ rapid migration from traditional on-premises environments to the cloud.

While many organizations have successfully extended their prevention and detection capabilities to the cloud, they are now experiencing another major gap: forensics and incident response.

Once something bad has been identified, understanding its true scope and impact is nearly impossible at times. The proliferation of cloud resources across a multitude of cloud providers, and the addition of container and serverless capabilities all add to the complexities. It’s clear that organizations need a better way to manage cloud incident response.

Security teams are looking to move past their homegrown solutions and open-source tools to incorporate real cloud forensics capabilities. However, with the increased buzz around cloud forensics, it can be challenging to decipher what is real cloud forensics, and what is “fauxrensics.”

This blog covers the five core capabilities that security teams should consider when evaluating a cloud forensics and incident response solution.

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1. Depth of data

There have been many conversations among the security community about whether cloud forensics is just log analysis. The reality, however, is that cloud forensics necessitates access to a robust dataset that extends far beyond traditional log data sources.

While logs provide valuable insights, a forensics investigation demands a deeper understanding derived from multiple data sources, including disk, network, and memory, within the cloud infrastructure. Full disk analysis complements log analysis, offering crucial context for identifying the root cause and scope of an incident.

For instance, when investigating an incident involving a Kubernetes cluster running on an EC2 instance, access to bash history can provide insights into the commands executed by attackers on the affected instance, which would not be available through cloud logs alone.

Having all of the evidence in one place is also a capability that can significantly streamline investigations, unifying your evidence be it disk images, memory captures or cloud logs, into a single timeline allowing security teams to reconstruct an attacks origin, path and impact far more easily. Multi–cloud environments also require platforms that can support aggregating data from many providers and services into one place. Doing this enables more holistic investigations and reduces security blind spots.

There is also the importance of collecting data from ephemeral resources in modern cloud and containerized environments. Critical evidence can be lost in seconds as resources are constantly spinning up and down, so having the ability to capture this data before its gone can be a huge advantage to security teams, rather than having to figure out what happened after the affected service is long gone.

darktrace / cloud, cado, cloud logs, ost, and memory information. value of cloud combined analysis

2. Chain of custody

Chain of custody is extremely critical in the context of legal proceedings and is an essential component of forensics and incident response. However, chain of custody in the cloud can be extremely complex with the number of people who have access and the rise of multi-cloud environments.

In the cloud, maintaining a reliable chain of custody becomes even more complex than it already is, due to having to account for multiple access points, service providers and third parties. Having automated evidence tracking is a must. It means that all actions are logged, from collection to storage to access. Automation also minimizes the chance of human error, reducing the risk of mistakes or gaps in evidence handling, especially in high pressure fast moving investigations.

The ability to preserve unaltered copies of forensic evidence in a secure manner is required to ensure integrity throughout an investigation. It is not just a technical concern, its a legal one, ensuring that your evidence handling is documented and time stamped allows it to stand up to court or regulatory review.

Real cloud forensics platforms should autonomously handle chain of custody in the background, recording and safeguarding evidence without human intervention.

3. Automated collection and isolation

When malicious activity is detected, the speed at which security teams can determine root cause and scope is essential to reducing Mean Time to Response (MTTR).

Automated forensic data collection and system isolation ensures that evidence is collected and compromised resources are isolated at the first sign of malicious activity. This can often be before an attacker has had the change to move latterly or cover their tracks. This enables security teams to prevent potential damage and spread while a deeper-dive forensics investigation takes place. This method also ensures critical incident evidence residing in ephemeral environments is preserved in the event it is needed for an investigation. This evidence may only exist for minutes, leaving no time for a human analyst to capture it.

Cloud forensics and incident response platforms should offer the ability to natively integrate with incident detection and alerting systems and/or built-in product automation rules to trigger evidence capture and resource isolation.

4. Ease of use

Security teams shouldn’t require deep cloud or incident response knowledge to perform forensic investigations of cloud resources. They already have enough on their plates.

While traditional forensics tools and approaches have made investigation and response extremely tedious and complex, modern forensics platforms prioritize usability at their core, and leverage automation to drastically simplify the end-to-end incident response process, even when an incident spans multiple Cloud Service Providers (CSPs).

Useability is a core requirement for any modern forensics platform. Security teams should not need to have indepth knowledge of every system and resource in a given estate. Workflows, automation and guidance should make it possible for an analyst to investigate whatever resource they need to.

Unifying the workflow across multiple clouds can also save security teams a huge amount of time and resources. Investigations can often span multiple CSP’s. A good security platform should provide a single place to search, correlate and analyze evidence across all environments.

Offering features such as cross cloud support, data enrichment, a single timeline view, saved search, and faceted search can help advanced analysts achieve greater efficiency, and novice analysts are able to participate in more complex investigations.

5. Incident preparedness

Incident response shouldn't just be reactive. Modern security teams need to regularly test their ability to acquire new evidence, triage assets and respond to threats across both new and existing resources, ensuring readiness even in the rapidly changing environments of the cloud.  Having the ability to continuously assess your incident response and forensics workflows enables you to rapidly improve your processes and identify and mitigate any gaps identified that could prevent the organization from being able to effectively respond to potential threats.

Real forensics platforms deliver features that enable security teams to prepare extensively and understand their shortcomings before they are in the heat of an incident. For example, cloud forensics platforms can provide the ability to:

  • Run readiness checks and see readiness trends over time
  • Identify and mitigate issues that could prevent rapid investigation and response
  • Ensure the correct logging, management agents, and other cloud-native tools are appropriately configured and operational
  • Ensure that data gathered during an investigation can be decrypted
  • Verify that permissions are aligned with best practices and are capable of supporting incident response efforts

Cloud forensics with Darktrace

Darktrace delivers a proactive approach to cyber resilience in a single cybersecurity platform, including cloud coverage. Darktrace / CLOUD is a real time Cloud Detection and Response (CDR) solution built with advanced AI to make cloud security accessible to all security teams and SOCs. By using multiple machine learning techniques, Darktrace brings unprecedented visibility, threat detection, investigation, and incident response to hybrid and multi-cloud environments.

Darktrace’s cloud offerings have been bolstered with the acquisition of Cado Security Ltd., which enables security teams to gain immediate access to forensic-level data in multi-cloud, container, serverless, SaaS, and on-premises environments.

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