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April 20, 2022

Email Compromise To Mass Phishing Campaign

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Apr 2022
Read Darktrace's in-depth analysis on the shift from business email compromise to mass phishing campaigns. Gain the knowledge to safeguard your business.

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

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Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
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March 25, 2025

Darktrace Recognized as the Only Visionary in the 2025 Gartner® Magic Quadrant™ for CPS Protection Platforms

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We are thrilled to announce that Darktrace has been named the only Visionary in the inaugural Gartner® Magic Quadrant™ for Cyber-Physical Systems (CPS) Protection Platforms. We feel This recognition highlights Darktrace’s AI-driven approach to securing industrial environments, where conventional security solutions struggle to keep pace with increasing cyber threats.

A milestone for CPS security

It's our opinion that the first-ever Gartner Magic Quadrant for CPS Protection Platforms reflects a growing industry shift toward purpose-built security solutions for critical infrastructure. As organizations integrate IT, OT, and cloud-connected systems, the cyber risk landscape continues to expand. Gartner evaluated 17 vendors based on their Ability to Execute and Completeness of Vision, establishing a benchmark for security leaders looking to enhance cyber resilience in industrial environments.

We believe the Gartner recognition of Darktrace as the only Visionary reaffirms the platform’s ability to proactively defend against cyber risks through AI-driven anomaly detection, autonomous response, and risk-based security strategies. With increasingly sophisticated attacks targeting industrial control systems, organizations need a solution that continuously evolves to defend against both known and unknown threats.

AI-driven security for CPS environments

Securing CPS environments requires an approach that adapts to the dynamic nature of industrial operations. Traditional security tools rely on static signatures and predefined rules, leaving gaps in protection against novel and sophisticated threats. Darktrace / OT takes a different approach, leveraging Self-Learning AI to detect and neutralize threats in real time, even in air-gapped or highly regulated environments.

Darktrace / OT continuously analyzes network behaviors to establish a deep understanding of what is “normal” for each industrial environment. This enables it to autonomously identify deviations that signal potential cyber threats, providing early warning and proactive defense before attacks can disrupt operations. Unlike rule-based security models that require constant manual updates, Darktrace / OT improves with the environment, ensuring long-term resilience against emerging cyber risks.

Bridging the IT-OT security gap

A major challenge for organizations protecting CPS environments is the disconnect between IT and OT security. While IT security has traditionally focused on data

protection and compliance, OT security is driven by operational uptime and safety, leading to siloed security programs that leave critical gaps in visibility and response.

Darktrace / OT eliminates these silos by providing unified visibility across IT, OT, and IoT assets, ensuring that security teams have a complete picture of their attack surface. Its AI-driven approach enables cross-domain threat detection, recognizing risks that move laterally between IT and OT environments. By seamlessly integrating with existing security architectures, Darktrace / OT helps organizations close security gaps without disrupting industrial processes.

Proactive OT risk management and resilience

Beyond detection and response, Darktrace / OT strengthens organizations’ ability to manage cyber risk proactively. By mapping vulnerabilities to real-world attack paths, it prioritizes remediation actions based on actual exploitability and business impact, rather than relying on isolated CVE scores. This risk-based approach enables security teams to focus resources where they matter most, reducing overall exposure to cyber threats.

With autonomous threat response capabilities, Darktrace / OT not only identifies risks but also contains them in real time, preventing attackers from escalating intrusions. Whether mitigating ransomware, insider threats, or sophisticated nation-state attacks, Darktrace / OT ensures that industrial environments remain secure, operational, and resilient, no matter how threats evolve.

AI-powered incident response and SOC automation

Security teams are facing an overwhelming volume of alerts, making it difficult to prioritize threats and respond effectively. Darktrace / OT’s Cyber AI Analyst acts as a force multiplier for security teams by automating threat investigation, alert triage, and response actions. By mimicking the workflow of a human SOC analyst, Cyber AI Analyst provides contextual insights that accelerate incident response and reduce the manual workload on security teams.

With 24/7 autonomous monitoring, Darktrace / OT ensures that threats are continuously detected and investigated in real time. Whether facing ransomware, insider threats, or sophisticated nation-state attacks, organizations can rely on AI-driven security to contain threats before they disrupt operations.

Trusted by customers: Darktrace / OT recognized in Gartner Peer Insights

Source: Gartner Peer Insights (Oct 28th)

Beyond our recognition in the Gartner Magic Quadrant, we feel Darktrace / OT is one of the highest-rated CPS security solutions on Gartner Peer Insights, reflecting strong customer trust and validation. With a 4.9/5 overall rating and the highest "Willingness to Recommend" score among CPS vendors, organizations across critical infrastructure and industrial sectors recognize the impact of our AI-driven security approach. Source: Gartner Peer Insights (Oct 28th)

This strong customer endorsement underscores why leading enterprises trust Darktrace / OT to secure their CPS environments today and in the future.

Redefining the future of CPS security

It's our view that Darktrace’s recognition as the only Visionary in the Gartner Magic Quadrant for CPS Protection Platforms validates its leadership in next-generation industrial security. As cyber threats targeting critical infrastructure continue to rise, organizations must adopt AI-driven security solutions that can adapt, respond, and mitigate risks in real time.

We believe this recognition reinforces our commitment to innovation and our mission to secure the world’s most essential systems. This recognition reinforces our commitment to innovation and our mission to secure the world’s most essential systems.

® Download the full Gartner Magic Quadrant for CPS Protection Platforms

® Request a demo to see Darktrace OT in action.

Gartner, Magic Quadrant for CPS Protection Platforms , Katell Thielemann, Wam Voster, Ruggero Contu 12 February 2025

Gartner does not endorse any vendor, product or service depicted in its research publications and does not advise technology users to select only those vendors with the highest ratings or other designation. Gartner research publications consist of the opinions of Gartner’s research organization and should not be construed as statements of fact. Gartner disclaims all warranties, expressed or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose.

GARTNER is a registered trademark and service mark of Gartner and Magic Quadrant and Peer Insights are a registered trademark, of Gartner, Inc. and/or its affiliates in the U.S. and internationally and are used herein with permission. All rights reserved. Gartner Peer Insights content consists of the opinions of individual end users based on their own experiences with the vendors listed on the platform, should not be construed as statements of fact, nor do they represent the views of Gartner or its affiliates. Gartner does not endorse any vendor, product or service depicted in this content nor makes any warranties, expressed or implied, with respect to this content, about its accuracy or completeness, including any warranties of merchantability or fitness for a particular purpose.

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Pallavi Singh
Product Marketing Manager, OT Security & Compliance

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March 25, 2025

Survey Findings: AI Cybersecurity Priorities and Objectives in 2025

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AI is changing the cybersecurity field, both on the offensive and defensive sides. We surveyed over 1,500 cybersecurity professionals from around the world to uncover their attitudes, understanding, and priorities when it comes to AI cybersecurity in 2025. Our full report, unearthing some telling trends, is available now.  

Download the full report to explore these findings in depth

It is clear that security professionals know their field is changing fast, and that AI will continue to influence those changes. Our survey results show that they are aware that the rise of AI will require them to adopt new tools and learn to use them effectively. Still, they aren’t always certain about how to plan for the future, or what to invest in.

The top priorities of security stakeholders for improving their defenses against AI-powered threats include augmenting their existing tool stacks with AI-powered solutions and improving integration among their security tools.

Figure 1: Year-over-year changes to the priorities of securitystakeholders.

Increasing cybersecurity staff

As was also the case last year, security stakeholders are less interested in hiring additional staff than in adding new AI-powered tools onto their existing security stacks, with only with 11% (and only 8% of executives) planning to increase cybersecurity staff in 2025.

This suggests that leaders are looking for new methods to overcome talent resource shortages.

Adding AI-powered security tools to supplement existing solutions

Executives are particularly enthusiastic about adopting AI-driven tools. Within that goal, there is consensus about the qualities cyber professionals are looking for when purchasing new security capabilities or replacing existing products.

  • 87% of survey respondents prefer solutions that are part of a broader platform over individual point products

These results are similar to last year’s, where again, almost nine out of ten agreed that a platform-oriented security solution was more effective at stopping cyber threats than a collection of individual products.

  • 88% of survey respondents agree that the use of AI within the security stack is critical to freeing up time for security teams to become more proactive, compared to reactive

AI itself can contribute to this shift from reactive to proactive security, improving risk prioritization and automating preventative strategies like Attack Surface Management (ASM) and proactive exposure management.

  • 84% of survey respondents prefer defensive AI solutions that do not require the organization’s data to be shared externally

This preference may reflect increasing attention to the data privacy and security risks posed by generative AI (gen AI) adoption. It may also reflect growing awareness of data residency requirements and other restrictions that regulators are imposing.

Improving cybersecurity awareness training for end users

Based on the survey results, practitioners in SecOps are more interested in improving security awareness training.

This goal is not necessarily mutually exclusive from the addition of AI tools. For example, teams can leverage AI to build more effective security awareness training programs, and as gen AI tools are adopted, users will need to be taught about data privacy and associated security risks.

Looking towards the future

One conclusion we can draw from the attitudinal shifts from last year’s survey to this year’s: while hiring more security staff might be a nice-to-have, implementing AI-powered tools so that existing employees can work smarter is increasingly viewed as a must-have.

However, trending goals are not just about managing resources, whether headcount or AI investments, to keep up with workloads. Existing end users must also be trained to follow safe practices while using established and newly adopted tools.

Security professionals, including executives, SecOps, and every role in between, continue to shift their identified challenges and priorities as they gear up for the coming year in the Era of AI.

State of AI report

Download the full report to explore these findings in depth

The full report for Darktrace’s State of AI Cybersecurity is out now. Download the paper to dig deeper into these trends, and see how results differ by industry, region, organization size, and job title.  

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