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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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June 18, 2025

Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision

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In today’s threat landscape, email remains the most targeted vector for cyberattacks. Organizations require not only multi-layered defenses but also advanced, integrated systems that work collaboratively to proactively mitigate threats before they cause damage

That’s why we’re proud to announce a new integration between Darktrace / EMAIL and Microsoft Defender for Office 365, delivering a Unified Quarantine experience that empowers security teams with seamless visibility, control, and response across both platforms.

This announcement builds on a strong and growing collaboration. In 2024, Darktrace was honored as Microsoft UK Partner of the Year and recognized as a Security Trailblazer at the annual Microsoft Security 20/20 Awards, a testament to our shared commitment to innovation and customer-centric security.

A Shared Mission: Stopping Threats at Machine Speed

This integration is more than a technical milestone,as it’s a reflection of a shared mission: to protect organizations from both known and unknown threats, with efficiency, accuracy, and transparency.

  • Microsoft Defender for Office 365 delivers a comprehensive security framework that safeguards Microsoft 365 email and collaboration workloads leveraging advanced AI, global threat intelligence and information on known attack infrastructure.
  • Darktrace / EMAIL complements this with Self-Learning AI that understands the unique communication patterns within each organization, detecting subtle anomalies that evade traditional detection methods.

Together, we’re delivering multi-layered, adaptive protection that’s greater than the sum of its parts.

“Our integration with Microsoft gives security teams the tools they need to act faster and more precisely to detect and respond to threats,” said Jill Popelka, CEO of Darktrace. “Together, we’re strengthening defenses where it matters most to our customers: at the inbox.”

Unified Quarantine: One View, Total Clarity

The new Unified Quarantine experience gives customers a single pane of glass to view and manage email threatsregardless of which product took action. This means:

  • Faster investigations with consolidated visibility
  • Clear attribution of actions and outcomes across both platforms
  • Streamlined workflows for security teams managing complex environments

“This integration is a testament to the power of combining Microsoft’s global threat intelligence with Darktrace’s unique ability to understand the ‘self’ of an organization,” said Jack Stockdale, CTO of Darktrace. “Together, we’re delivering a new standard in proactive, adaptive email security.”

A New Era of Collaborative Cyber Defense

This collaboration represents a broader shift in cybersecurity: from siloed tools to integrated ecosystems. As attackers become more sophisticated, defenders must move faster, smarter, and in unison.

Through this integration, Darktrace and Microsoft establish a new standard for collaboration between native and third-party security solutions, enhancing not only threat detection but also comprehensive understanding and proactive measures against threats.

We’re excited to bring this innovation to our customers and continue building a future where AI and human expertise collaborate to secure the enterprise.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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June 18, 2025

Customer Case Study: Leading Petrochemical Manufacturer

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Headquartered in Saudi Arabia, this industry leading petrochemical manufacturer serves customers in more than 80 countries across diverse markets throughout Europe, Africa, Latin America, the Middle East, China, and Southeast Asia.

Cyber resiliency critical to growth strategy

This leading petrochemical manufacturer’s vision is to be one of the major global players in the production and marketing of designated petrochemicals and downstream products. The company aims to significantly increase its capacity to up to a million metric tons within the next few years.

With cyber-attacks on critical infrastructure increasing 30% globally last year, cyber resiliency is essential to supporting the company’s strategic business goals of:

  • Maximizing production through efficient asset utilization
  • Maximizing sales by conducting 90% of its business outside Saudi Arabia
  • Optimizing resources and processes by integrating with UN Global Compact principles for sustainability and efficiency
  • Growing its business portfolio by engaging in joint ventures to diversify production and add value to the economy

However, the industry leader faced several challenges in its drive to fortify its cybersecurity defenses.

Visibility gaps delay response time

The company’s existing security setup provided limited visibility to the in-house security team, hindering its ability to detect anomalous network and user activity in real time. This resulted in delayed responses to potential incidents, making proactive issue resolution difficult and any remediation in the event of a successful attack costly and time-consuming.

Manual detection drains resources

Without automated detection and response capabilities, the organization’s security team had to manually monitor for suspicious activity – a time-consuming and inefficient approach that strained resources and left the organization vulnerable. This made it difficult for the team to stay current with training or acquire new skills and certifications, which are core to the ethos of both the company’s owners and the team itself.

Cyber-attacks on critical infrastructure increasing

The petrochemical manufacturer is part of a broader ecosystem of companies, making the protection of its supply chain – both upstream and downstream – critical. With several manufacturing entities and multiple locations, the customer’s internal structure is complex and challenging to secure. As cyber-attacks on critical infrastructure escalate, it needed a more comprehensive approach to safeguard its business and the wider ecosystem.

Keeping and growing skills and focus in-house

To strengthen its cybersecurity strategy, the company considered two options:

  1. Make a significant initial and ongoing investment in a Security Operations Center (SOC), which would involve skills development outside the company and substantial management overhead.
  2. Use a combination of new, automated tools and an outsourced Managed Detection and Response (MDR) service to reduce the burden on internal security specialists and allow the company to invest in upskilling its staff so they can focus on more strategic tasks.

Faced with this choice between entirely outsourcing security and augmenting the security team with new capabilities, the customer chose the second option, selecting Darktrace to automate the company’s monitoring, detection, and response. Today, the petrochemical manufacturer is using:

Extending the SOC with 24/7 expert support

To alleviate the burden on its lean security team, the company augmented its in-house capabilities with Darktrace’s Managed Detection & Response service. This support acts as an extension of its SOC, providing 24/7 monitoring, investigation, and escalation of high-priority threats. With Darktrace’s global SOC managing alert triage and autonomously containing threats, the organization’s internal team can focus on strategic initiatives. The result is a stronger security posture and increased capacity to proactively address evolving cyber risks – without expanding headcount or sacrificing visibility.

A unique approach to AI

In its search for a new security platform, the company’s Director of Information Technology said Darktrace’s autonomous response capability, coupled with Self-Learning AI-driven threat reduction, were two big reasons for selecting Darktrace over competing products and services.

AI was a huge factor – no one else was doing what Darktrace was doing with [AI].”

Demonstrated visibility

Before Darktrace, the customer had no visibility into the network activity to and from remote worker devices. Some employees need the ability to connect to its networks at any time and from any location, including the Director of Information Technology. The trial deployment of Darktrace / ENDPOINT was a success and gave the team peace of mind that, no matter the location or device, high-value remote workers were protected by Darktrace.

Modular architecture  

Darktrace's modular architecture allowed the company to deploy security controls across its complex, multi-entity environment. The company’s different locations run on segregated networks but are still interconnected and need to be protected. Darktrace / NETWORK provides a unified view and coordinated security response across the organization’s entire network infrastructure, including endpoint devices.

Results

The petrochemical manufacturer is using Darktrace across all of its locations and has achieved total visibility across network and user activity. “Darktrace is increasing in value every day,” said the Director of Information Technology.

I don’t have a big team, and Darktrace makes our lives very, very easy, not least the automation of some of the tasks that require constant manual review.”

Time savings frees analysts to focus on proactive security

Darktrace / NETWORK provides continuous, AI-driven monitoring and analysis of the company’s network activity, user behavior, and threat patterns, establishing a baseline of what normal activity looks like, and then alerting analysts to any deviations from normal traffic, activity, and behaviors. Darktrace’s autonomous response capabilities speed up response to detected threats, meaning intervention from the security team is required for fewer incidents and alerts.

In October 2024 alone, Darktrace Cyber AI Analyst saved the team 810 investigation hours, and autonomously responded to 180 anomalous behaviors that were uncovered during the investigations. With Darktrace managing the majority of threat detection and response efforts, the security team has been able to change its day-to-day activity from manual review of traffic and alerts and belated response to activity, to proactively fortifying its detection and response posture and upskilling to meet evolving requirements.  

Layered email protection reduces phishing threats

The company’s email infrastructure posed a challenge due to petrochemical industry regulations requiring on-premises email servers, with some security delivered via Microsoft Azure. By integrating Darktrace / EMAIL into the Azure stack, the organization has reduced the volume of phishing emails its users receive by 5%.

“Now we have one more layer of security related to email – every email goes through two filters. If something is not being caught or traced by Azure, it is being detected by Darktrace,” said the Director of Information Technology. “As a result, we’re now seeing only about 15% to 20% of the phishing emails we used to receive before implementing Darktrace.”

Preparing for a secure future

The time saved using Darktrace has helped the security team take proactive steps, including preparing for new cyber resilience regulations for Saudi Arabia’s Critical National Infrastructure, as mandated by the National Cybersecurity Authority (NCA).

“The team now has ample time to prepare policies and procedures that meet the new NCA regulations and, in some cases, enhance the requirements of the new law,” said the Director of Information Technology. “All of this is possible because they don’t need to keep watch; Darktrace takes on so much of that task for them.”

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