Blog
/
Email
/
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
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
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

More in this series

No items found.

Blog

/

/

September 23, 2025

It’s Time to Rethink Cloud Investigations

cloud investigationsDefault blog imageDefault blog image

Cloud Breaches Are Surging

Cloud adoption has revolutionized how businesses operate, offering speed, scalability, and flexibility. But for security teams, this transformation has introduced a new set of challenges, especially when it comes to incident response (IR) and forensic investigations.

Cloud-related breaches are skyrocketing – 82% of breaches now involve cloud-stored data (IBM Cost of a Data Breach, 2023). Yet incidents often go unnoticed for days: according to a 2025 report by Cybersecurity Insiders, of the 65% of organizations experienced a cloud-related incident in the past year, only 9% detected it within the first hour, and 62% took more than 24 hours to remediate it (Cybersecurity Insiders, Cloud Security Report 2025).

Despite the shift to cloud, many investigation practices remain rooted in legacy on-prem approaches. According to a recent report, 65% of organizations spend approximately 3-5 days longer when investigating an incident in the cloud vs. on premises.

Cloud investigations must evolve, or risk falling behind attackers who are already exploiting the cloud’s speed and complexity.

4 Reasons Cloud Investigations Are Broken

The cloud’s dynamic nature – with its ephemeral workloads and distributed architecture – has outpaced traditional incident response methods. What worked in static, on-prem environments simply doesn’t translate.

Here’s why:

  1. Ephemeral workloads
    Containers and serverless functions can spin up and vanish in minutes. Attackers know this as well – they’re exploiting short-lived assets for “hit-and-run” attacks, leaving almost no forensic footprint. If you’re relying on scheduled scans or manual evidence collection, you’re already too late.
  2. Fragmented tooling
    Each cloud provider has its own logs, APIs, and investigation workflows. In addition, not all logs are enabled by default, cloud providers typically limit the scope of their logs (both in terms of what data they collect and how long they retain it), and some logs are only available through undocumented APIs. This creates siloed views of attacker activity, making it difficult to piece together a coherent timeline. Now layer in SaaS apps, Kubernetes clusters, and shadow IT — suddenly you’re stitching together 20+ tools just to find out what happened. Analysts call it the ‘swivel-chair Olympics,’ and it’s burning hours they don’t have.
  3. SOC overload
    Analysts spend the bulk of their time manually gathering evidence and correlating logs rather than responding to threats. This slows down investigations and increases burnout. SOC teams are drowning in noise; they receive thousands of alerts a day, the majority of which never get touched. False positives eat hundreds of hours a month, and consequently burnout is rife.  
  4. Cost of delay
    The longer an investigation takes, the higher its cost. Breaches contained in under 200 days save an average of over $1M compared to those that linger (IBM Cost of a Data Breach 2025).

These challenges create a dangerous gap for threat actors to exploit. By the time evidence is collected, attackers may have already accessed or exfiltrated data, or entrenched themselves deeper into your environment.

What’s Needed: A New Approach to Cloud Investigations

It’s time to ditch the manual, reactive grind and embrace investigations that are automated, proactive, and built for the world you actually defend. Here’s what the next generation of cloud forensics must deliver:

  • Automated evidence acquisition
    Capture forensic-level data the moment a threat is detected and before assets disappear.
  • Unified multi-cloud visibility
    Stitch together logs, timelines, and context across AWS, Azure, GCP, and hybrid environments into a single unified view of the investigation.
  • Accelerated investigation workflows
    Reduce time-to-insight from hours or days to minutes with automated analysis of forensic data, enabling faster containment and recovery.
  • Empowered SOC teams
    Fully contextualised data and collaboration workflows between teams in the SOC ensure seamless handover, freeing up analysts from manual collection tasks so they can focus on what matters: analysis and response.

Attackers are already leveraging the cloud’s agility. Defenders must do the same — adopting solutions that match the speed and scale of modern infrastructure.

Cloud Changed Everything. It’s Time to Change Investigations.  

The cloud fundamentally reshaped how businesses operate. It’s time for security teams to rethink how they investigate threats.

Forensics can no longer be slow, manual, and reactive. It must be instant, automated, and cloud-first — designed to meet the demands of ephemeral infrastructure and multi-cloud complexity.

The future of incident response isn’t just faster. It’s smarter, more scalable, and built for the environments we defend today, not those of ten years ago.  

On October 9th, Darktrace is revealing the next big thing in cloud security. Don’t miss it – sign up for the webinar.

darktrace live event launch
Continue reading
About the author
Kellie Regan
Director, Product Marketing - Cloud Security

Blog

/

/

September 22, 2025

Understanding the Canadian Critical Cyber Systems Protection Act

Canadian critical cyber systems protection actDefault blog imageDefault blog image

Introduction: The Canadian Critical Cyber Systems Protection Act

On 18 June 2025, the Canadian federal Government introduced Bill C-8 which, if adopted following completion of the legislative process, will enact the Critical Cyber Systems Protection Act (CCSPA) and give Canada its first federal, cross-sector and legally binding cybersecurity regime for designated critical infrastructure providers. As of August 2025, the Bill has completed first reading and stands at second reading in the Canadian House of Commons.

Political context

The measure revives most of the stalled 2022 Bill C-26 “An Act Respecting Cyber Security” which “died on Paper” when Parliament was prorogued in January 2025, in the wake of former Prime Minister Justin Trudeau’s resignation.

The new government, led by Mark Carney since March 2025, has re-tabled the package with the same two-part structure: (1) amendments to the Telecommunications Act that enable security directions to telecoms; and (2) a new CCSPA setting out mandatory cybersecurity duties for designated operators. This blog focuses on the latter.

If enacted, Canada will join fellow Five Eyes partners such as the United Kingdom and Australia, which already impose statutory cyber-security duties on operators of critical national infrastructure.

The case for new cybersecurity legislation in Canada

The Canadian cyber threat landscape has expanded. The country's national cyber authority, the Canadian Centre for Cybersecurity (Cyber Centre), recently assessed that the number of cyber incidents has “sharply increased” in the last two years, as has the severity of those incidents, with essential services providers among the targets. Likewise, in its 2025-2026 National Cyber Threat Assessment, the Cyber Centre warned that AI technologies are “amplifying cyberspace threats” by lowering barriers to entry, improving the speed and sophistication of social-engineering attacks and enabling more precise operations.

This context mirrors what we are seeing globally: adversaries, including state actors, are taking advantage of the availability and sophistication of AI tools, which they have leverage to amplify the effectiveness of their operations. In this increasingly complex landscape, regulation must keep pace and evolve in step with the risk.

What the Canadian Critical Cyber Systems Protection Act aims to achieve

  • If enacted, the CCSPA will apply to operators in federally regulated critical infrastructure sectors which are vital to national security and public safety, as further defined in “Scope” below (the “Regulated Entities”), to adopt and comply with a minimum standard of cybersecurity duties (further described below)  which align with those its Five Eyes counterparts are already adhering to.

Who does the CCSPA apply to

The CCSPA would apply to designated operators that deliver services or systems within federal jurisdiction in the following priority areas:

  • telecommunications services
  • interprovincial or international pipeline and power line systems, nuclear energy systems, transportation systems
  • banking and clearing  
  • settlement systems

The CCSPA would also grant the Governor in Council (Federal Cabinet) with powers to add or remove entities in scope via regulation.

Scope of the CCSPA

The CCSPA introduces two key instruments:

First, it strengthens cyber threat information sharing between responsible ministers, sector regulators, and the Communications Security Establishment (through the Cyber Centre).

Second, it empowers the Governor in Council (GIC) to issue Cyber Security Directions (CSDs) - binding orders requiring a designated operator to implement specified measures to protect a critical cyber system within defined timeframes.

CSDs may be tailored to an individual operator or applied to a class of operators and can address technology, process, or supplier risks. To safeguard security and commercial confidentiality, the CCSPA restricts disclosure of the existence or content of a CSD except as necessary to carry it out.

Locating decision-making with the GIC ensures that CSDs are made with a cross-government view that weighs national security, economic priorities and international agreement.

New obligations for designated providers

The CCSPA would impose key cybersecurity compliance and obligations on designated providers. As it stands, this includes:

  1. Establishing and maintaining cybersecurity programs: these will need to be comprehensive, proportionate and developed proactively. Once implemented, they will need to be continuously reviewed
  2. Mitigating supply chain risks: Regulated Entities will be required to assess their third-party products and services by conducting a supply chain analysis, and take active steps to mitigate any identified risks
  3. Reporting incidents:  Regulated Entities will need to be more transparent with their reporting, by making the Communications Security Establishment (CSE) aware of any incident which has, or could potentially have, an impact on a critical system. The reports must be made within specific timelines, but in any event within no more than 72 hours;
  4. Compliance with cybersecurity directions:  the government will, under the CCSPA, have the authority to issue cybersecurity directives in an effort to remain responsive to emerging threats, which Regulated Entities will be required to follow once issued
  5. Record keeping: this shouldn’t be a surprise to many of those Regulated Entities which fall in scope, which are already likely to be subject to record keeping requirements. Regulated Entities should expect to be maintaining records and conducting audits of their systems and processes against the requirements of the CCSPA

It should be noted, however, that this may be subject to change, so Regulated Entities should keep an eye on the progress of the Bill as it makes its way through parliament.

Enforcement of the Act would be carried out by sector-specific regulators identified in the Act such as the Office of the Superintendent of Financial Institutions, Minister of Transport, Canada Energy Regulator, Canadian Nuclear Safety Commission and the Ministry of Industry.

What are the penalties for CCSPA non-compliance?

When assessing the penalties associated with non-compliance with the requirements of the CCSPA, it is clear that such non-compliance will be taken seriously, and the severity of the penalties follows the trend of those applied by the European Union to key pieces of EU legislation. The “administrative monetary penalties” (AMPs) set by regulation could see fines being applied of up to C$1 million for individuals and up to C$15 million for organizations.

Continue reading
About the author
The Darktrace Community
Your data. Our AI.
Elevate your network security with Darktrace AI