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.

Written by

Shuh Chin Goh

Written by

Sam Lister

SOC Analyst

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

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

Written by

Shuh Chin Goh

Written by

Sam Lister

SOC Analyst

Senior Product Marketing Manager, Email

Watch the NIS2 Webinar

Blog

Identity

July 3, 2025

Top Eight Threats to SaaS Security and How to Combat Them

The latest on the identity security landscape

Following the mass adoption of remote and hybrid working patterns, more critical data than ever resides in cloud applications – from Salesforce and Google Workspace, to Box, Dropbox, and Microsoft 365.

On average, a single organization uses 130 different Software-as-a-Service (SaaS) applications, and 45% of organizations reported experiencing a cybersecurity incident through a SaaS application in the last year.

As SaaS applications look set to remain an integral part of the digital estate, organizations are being forced to rethink how they protect their users and data in this area.

What is SaaS security?

SaaS security is the protection of cloud applications. It includes securing the apps themselves as well as the user identities that engage with them.

Below are the top eight threats that target SaaS security and user identities.

1. Account Takeover (ATO)

Attackers gain unauthorized access to a user’s SaaS or cloud account by stealing credentials through phishing, brute-force attacks, or credential stuffing. Once inside, they can exfiltrate data, send malicious emails, or escalate privileges to maintain persistent access.

2. Privilege escalation

Cybercriminals exploit misconfigurations, weak access controls, or vulnerabilities to increase their access privileges within a SaaS or cloud environment. Gaining admin or superuser rights allows attackers to disable security settings, create new accounts, or move laterally across the organization.

3. Lateral movement

Once inside a network or SaaS platform, attackers move between accounts, applications, and cloud workloads to expand their foot- hold. Compromised OAuth tokens, session hijacking, or exploited API connections can enable adversaries to escalate access and exfiltrate sensitive data.

4. Multi-Factor Authentication (MFA) bypass and session hijacking

Threat actors bypass MFA through SIM swapping, push bombing, or exploiting session cookies. By stealing an active authentication session, they can access SaaS environments without needing the original credentials or MFA approval.

5. OAuth token abuse

Attackers exploit OAuth authentication mechanisms by stealing or abusing tokens that grant persistent access to SaaS applications. This allows them to maintain access even if the original user resets their password, making detection and mitigation difficult.

6. Insider threats

Malicious or negligent insiders misuse their legitimate access to SaaS applications or cloud platforms to leak data, alter configurations, or assist external attackers. Over-provisioned accounts and poor access control policies make it easier for insiders to exploit SaaS environments.

7. Application Programming Interface (API)-based attacks

SaaS applications rely on APIs for integration and automation, but attackers exploit insecure endpoints, excessive permissions, and unmonitored API calls to gain unauthorized access. API abuse can lead to data exfiltration, privilege escalation, and service disruption.

8. Business Email Compromise (BEC) via SaaS

Adversaries compromise SaaS-based email platforms (e.g., Microsoft 365 and Google Workspace) to send phishing emails, conduct invoice fraud, or steal sensitive communications. BEC attacks often involve financial fraud or data theft by impersonating executives or suppliers.

BEC heavily uses social engineering techniques, tailoring messages for a specific audience and context. And with the growing use of generative AI by threat actors, BEC is becoming even harder to detect. By adding ingenuity and machine speed, generative AI tools give threat actors the ability to create more personalized, targeted, and convincing attacks at scale.

Protecting against these SaaS threats

Traditionally, security leaders relied on tools that were focused on the attack, reliant on threat intelligence, and confined to a single area of the digital estate.

However, these tools have limitations, and often prove inadequate for contemporary situations, environments, and threats. For example, they may lack advanced threat detection, have limited visibility and scope, and struggle to integrate with other tools and infrastructure, especially cloud platforms.

AI-powered SaaS security stays ahead of the threat landscape

New, more effective approaches involve AI-powered defense solutions that understand the digital business, reveal subtle deviations that indicate cyber-threats, and action autonomous, targeted responses.

[related-resource]

‍

About the author

Carlos Gray

Senior Product Marketing Manager, Email

Blog

July 2, 2025

Pre-CVE Threat Detection: 10 Examples Identifying Malicious Activity Prior to Public Disclosure of a Vulnerability

‍

Vulnerabilities are weaknesses in a system that can be exploited by malicious actors to gain unauthorized access or to disrupt normal operations. Common Vulnerabilities and Exposures (or CVEs) are a list of publicly disclosed cybersecurity vulnerabilities that can be tracked and mitigated by the security community.

When a vulnerability is discovered, the standard practice is to report it to the vendor or the responsible organization, allowing them to develop and distribute a patch or fix before the details are made public. This is known as responsible disclosure.

With a record-breaking 40,000 CVEs reported for 2024 and a predicted higher number for 2025 by the Forum for Incident Response and Security Teams (FIRST) [1], anomaly-detection is essential for identifying these potential risks. The gap between exploitation of a zero-day and disclosure of the vulnerability can sometimes be considerable, and retroactively attempting to identify successful exploitation on your network can be challenging, particularly if taking a signature-based approach.

Detecting threats without relying on CVE disclosure

Abnormal behaviors in networks or systems, such as unusual login patterns or data transfers, can indicate attempted cyber-attacks, insider threats, or compromised systems. Since Darktrace does not rely on rules or signatures, it can detect malicious activity that is anomalous even without full context of the specific device or asset in question.

‍For example, during the Fortinet exploitation late last year, the Darktrace Threat Research team were investigating a different Fortinet vulnerability, namely CVE 2024-23113, for exploitation when Mandiant released a security advisory around CVE 2024-47575, which aligned closely with Darktrace’s findings.

Retrospective analysis like this is used by Darktrace’s threat researchers to better understand detections across the threat landscape and to add additional context.

Below are ten examples from the past year where Darktrace detected malicious activity days or even weeks before a vulnerability was publicly disclosed.

ten examples from the past year where Darktrace detected malicious activity days or even weeks before a vulnerability was publicly disclosed.

Trends in pre-cve exploitation

Often, the disclosure of an exploited vulnerability can be off the back of an incident response investigation related to a compromise by an advanced threat actor using a zero-day. Once the vulnerability is registered and publicly disclosed as having been exploited, it can kick off a race between the attacker and defender: attack vs patch.

Nation-state actors, highly skilled with significant resources, are known to use a range of capabilities to achieve their target, including zero-day use. Often, pre-CVE activity is “low and slow”, last for months with high operational security. After CVE disclosure, the barriers to entry lower, allowing less skilled and less resourced attackers, like some ransomware gangs, to exploit the vulnerability and cause harm. This is why two distinct types of activity are often seen: pre and post disclosure of an exploited vulnerability.

Darktrace saw this consistent story line play out during several of the Fortinet and PAN OS threat actor campaigns highlighted above last year, where nation-state actors were seen exploiting vulnerabilities first, followed by ransomware gangs impacting organizations [2].

The same applies with the recent SAP Netweaver exploitations being tied to a China based threat actor earlier this spring with subsequent ransomware incidents being observed [3].

Autonomous Response

Anomaly-based detection offers the benefit of identifying malicious activity even before a CVE is disclosed; however, security teams still need to quickly contain and isolate the activity.

For example, during the Ivanti chaining exploitation in the early part of 2025, a customer had Darktrace’s Autonomous Response capability enabled on their network. As a result, Darktrace was able to contain the compromise and shut down any ongoing suspicious connectivity by blocking internal connections and enforcing a “pattern of life” on the affected device.

This pre-CVE detection and response by Darktrace occurred 11 days before any public disclosure, demonstrating the value of an anomaly-based approach.

In some cases, customers have even reported that Darktrace stopped malicious exploitation of devices several days before a public disclosure of a vulnerability.

For example, During the ConnectWise exploitation, a customer informed the team that Darktrace had detected malicious software being installed via remote access. Upon further investigation, four servers were found to be impacted, while Autonomous Response had blocked outbound connections and enforced patterns of life on impacted devices.

Conclusion

By continuously analyzing behavioral patterns, systems can spot unusual activities and patterns from users, systems, and networks to detect anomalies that could signify a security breach.

Through ongoing monitoring and learning from these behaviors, anomaly-based security systems can detect threats that traditional signature-based solutions might miss, while also providing detailed insights into threat tactics, techniques, and procedures (TTPs). This type of behavioral intelligence supports pre-CVE detection, allows for a more adaptive security posture, and enables systems to evolve with the ever-changing threat landscape.

Credit to Nathaniel Jones (VP, Security & AI Strategy, Field CISO), Emma Fougler (Global Threat Research Operations Lead), Ryan Traill (Analyst Content Lead)

References and further reading:

Related Darktrace blogs:

‍

*Self-reported by customer, confirmed afterwards.

**Updated January 2024 blog now reflects current findings

About the author

Your data. Our AI.

Elevate your network security with Darktrace AI

Get a demo

Email Compromise To Mass Phishing Campaign

Attack summary

Attack timeline

Darktrace guidance

MITRE ATT&CK techniques observed

Footnotes

Pre-CVE Threat Detection: 10 Examples Identifying Malicious Activity Prior to Public Disclosure of a Vulnerability

Top Eight Threats to SaaS Security and How to Combat Them

Enjoying the blog?

More in this series

Why attack-centric approaches to email security can’t cope with modern threats

Evaluating Email Security: How to Select the Best Solution for Your Organization

Why Data Classification Isn’t Enough to Prevent Data Loss

Blog

Identity

July 3, 2025

Top Eight Threats to SaaS Security and How to Combat Them

The latest on the identity security landscape

What is SaaS security?

1. Account Takeover (ATO)

2. Privilege escalation

3. Lateral movement

4. Multi-Factor Authentication (MFA) bypass and session hijacking

5. OAuth token abuse

6. Insider threats

7. Application Programming Interface (API)-based attacks

8. Business Email Compromise (BEC) via SaaS

Protecting against these SaaS threats

AI-powered SaaS security stays ahead of the threat landscape

Blog

July 2, 2025

Pre-CVE Threat Detection: 10 Examples Identifying Malicious Activity Prior to Public Disclosure of a Vulnerability

Detecting threats without relying on CVE disclosure

Below are ten examples from the past year where Darktrace detected malicious activity days or even weeks before a vulnerability was publicly disclosed.

Trends in pre-cve exploitation

Autonomous Response

Conclusion

References and further reading:

Related Darktrace blogs: