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April 30, 2024

Detecting Attacks Across Email, SaaS, and Network Environments with Darktrace’s ActiveAI Security Platform

This blog explores how Darktrace’s combined AI approach enabled it to identify and connect an attack that took place over three critical areas of a customer’s digital environment, namely email, SaaS and network.
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
Zoe Tilsiter
Cyber Analyst
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30
Apr 2024

The State of AI in Cybersecurity

In a recent survey outlined in Darktrace’s State of AI Cyber Security whitepaper, 95% of cyber security professionals agree that AI-powered security solutions will improve their organization’s detection of cyber-threats [1]. Crucially, a combination of multiple AI methods is the most effective to improve cybersecurity; improving threat detection, accelerating threat investigation and response, and providing visibility across an organization’s digital environment.

In March 2024, Darktrace’s AI-led security platform was able to detect suspicious activity affecting a customer’s email, Software-as-a-Service (SaaS), and network environments, whilst its applied supervised learning capability, Cyber AI Analyst, autonomously correlated and connected all of these events together in one single incident, explained concisely using natural language processing.

Attack Overview

Following an initial email attack vector, an attacker logged into a compromised SaaS user account from the Netherlands, changed inbox rules, and leveraged the account to send thousands of phishing emails to internal and external users. Internal users fell victim to the emails by clicking on contained suspicious links that redirected them to newly registered suspicious domains hosted on same IP address as the hijacked SaaS account login. This activity triggered multiple alerts in Darktrace DETECT™ on both the network and SaaS side, all of which were correlated into one Cyber AI Analyst incident.

In this instance, Darktrace RESPOND™ was not active on any of the customer’s environments, meaning the compromise was able to escalate until their security team acted on the alerts raised by DETECT. Had RESPOND been enabled at the time of the attack, it would have been able to apply swift actions to contain the attack by blocking connections to suspicious endpoints on the network side and disabling users deviating from their normal behavior on the customer’s SaaS environment.

Nevertheless, thanks to DETECT and Cyber AI Analyst, Darktrace was able to provide comprehensive visibility across the customer’s three digital estate environments, decreasing both investigation and response time which enabled them to quickly enact remediation during the attack. This highlights the crucial role that Darktrace’s combined AI approach can play in anomaly detection cyber defense

Attack Details & Darktrace Coverage

Attack timeline

1. Email: the initial attack vector  

The initial attack vector was likely email, as on March 18, 2024, Darktrace observed a user device making several connections to the email provider “zixmail[.]net”, shortly before it connected to the first suspicious domain. Darktrace/Email identified multiple unusual inbound emails from an unknown sender that contained a suspicious link. Darktrace recognized these emails as potentially malicious and locked the link, ensuring that recipients could not directly click it.

Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.
Figure 1: Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.

2. Escalation to Network

Later that day, despite Darktrace/Email having locked the link in the suspicious email, the user proceeded to click on it and was directed to a suspicious external location, namely “rz8js7sjbef[.]latovafineart[.]life”, which triggered the Darktrace/Network DETECT model “Suspicious Domain”. Darktrace/Email was able to identify that this domain had only been registered 4 days before this activity and was hosted on an IP address based in the Netherlands, 193.222.96[.]9.

3. SaaS Account Hijack

Just one minute later, Darktrace/Apps observed the user’s Microsoft 365 account logging into the network from the same IP address. Darktrace understood that this represented unusual SaaS activity for this user, who had only previously logged into the customer’s SaaS environment from the US, triggering the “Unusual External Source for SaaS Credential Use” model.

4. SaaS Account Updates

A day later, Darktrace identified an unusual administrative change on the user’s Microsoft 365 account. After logging into the account, the threat actor was observed setting up a new multi-factor authentication (MFA) method on Microsoft Authenticator, namely requiring a 6-digit code to authenticate. Darktrace understood that this authentication method was different to the methods previously used on this account; this, coupled with the unusual login location, triggered the “Unusual Login and Account Update” DETECT model.

5. Obfuscation Email Rule

On March 20, Darktrace detected the threat actor creating a new email rule, named “…”, on the affected account. Attackers are typically known to use ambiguous or obscure names when creating new email rules in order to evade the detection of security teams and endpoints users.

The parameters for the email rule were:

“AlwaysDeleteOutlookRulesBlob: False, Force: False, MoveToFolder: RSS Feeds, Name: ..., MarkAsRead: True, StopProcessingRules: True.”

This rule was seemingly created with the intention of obfuscating the sending of malicious emails, as the rule would move sent emails to the "RSS Feeds” folder, a commonly used tactic by attackers as the folder is often left unchecked by endpoint users. Interestingly, Darktrace identified that, despite the initial unusual login coming from the Netherlands, the email rule was created from a different destination IP, indicating that the attacker was using a Virtual Private Network (VPN) after gaining a foothold in the network.

Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.
Figure 2: Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.

6. Outbound Phishing Emails Sent

Later that day, the attacker was observed using the compromised customer account to send out numerous phishing emails to both internal and external recipients. Darktrace/Email detected a significant spike in inbound emails on the compromised account, with the account receiving bounce back emails or replies in response to the phishing emails. Darktrace further identified that the phishing emails contained a malicious DocSend link hidden behind the text “Click Here”, falsely claiming to be a link to the presentation platform Prezi.

Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.
Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.

7. Suspicious Domains and Redirects

After the phishing emails were sent, multiple other internal users accessed the DocSend link, which directed them to another suspicious domain, “thecalebgroup[.]top”, which had been registered on the same day and was hosted on the aforementioned Netherlands-based IP, 193.222.96[.]91. At the time of the attack, this domain had not been reported by any open-source intelligence (OSINT), but it has since been flagged as malicious by multiple vendors [2].

External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.
Figure 4: External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.  

8. Cyber AI Analyst’s Investigation

As this attack was unfolding, Darktrace’s Cyber AI Analyst was able to autonomously investigate the events, correlating them into one wider incident and continually adding a total of 14 new events to the incident as more users fell victim to the phishing links.

Cyber AI Analyst successfully weaved together the initial suspicious domain accessed in the initial email attack vector (Figure 5), the hijack of the SaaS account from the Netherlands IP (Figure 6), and the connection to the suspicious redirect link (Figure 7). Cyber AI Analyst was also able to uncover other related activity that took place at the time, including a potential attempt to exfiltrate data out of the customer’s network.

By autonomously analyzing the thousands of connections taking place on a network at any given time, Darktrace’s Cyber AI Analyst is able to detect seemingly separate anomalous events and link them together in one incident. This not only provides organizations with full visibility over potential compromises on their networks, but also saves their security teams precious time ensuring they can quickly scope out the ongoing incident and begin remediation.

Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.
Figure 7: Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.

Conclusion

In this scenario, Darktrace demonstrated its ability to detect and correlate suspicious activities across three critical areas of a customer’s digital environment: email, SaaS, and network.

It is essential that cyber defenders not only adopt AI but use a combination of AI technology capable of learning and understanding the context of an organization’s entire digital infrastructure. Darktrace’s anomaly-based approach to threat detection allows it to identify subtle deviations from the expected behavior in network devices and SaaS users, indicating potential compromise. Meanwhile, Cyber AI Analyst dynamically correlates related events during an ongoing attack, providing organizations and their security teams with the information needed to respond and remediate effectively.

Credit to Zoe Tilsiter, Analyst Consulting Lead (EMEA), Brianna Leddy, Director of Analysis

Appendices

References

[1] https://darktrace.com/state-of-ai-cyber-security

[2] https://www.virustotal.com/gui/domain/thecalebgroup.top

Darktrace DETECT Model Coverage

SaaS Models

- SaaS / Access / Unusual External Source for SaaS Credential Use

- SaaS / Compromise / Unusual Login and Account Update

- SaaS / Compliance / Anomalous New Email Rule

- SaaS / Compromise / Unusual Login and New Email Rule

Network Models

- Device / Suspicious Domain

- Multiple Device Correlations / Multiple Devices Breaching Same Model

Cyber AI Analyst Incidents

- Possible Hijack of Office365 Account

- Possible SSL Command and Control

Indicators of Compromise (IoCs)

IoC – Type – Description

193.222.96[.]91 – IP – Unusual Login Source

thecalebgroup[.]top – Domain – Possible C2 Endpoint

rz8js7sjbef[.]latovafineart[.]life – Domain – Possible C2 Endpoint

https://docsend[.]com/view/vcdmsmjcskw69jh9 - Domain - Phishing Link

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
Zoe Tilsiter
Cyber Analyst

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April 14, 2025

Email bombing exposed: Darktrace’s email defense in action

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What is email bombing?

An email bomb attack, also known as a "spam bomb," is a cyberattack where a large volume of emails—ranging from as few as 100 to as many as several thousand—are sent to victims within a short period.

How does email bombing work?

Email bombing is a tactic that typically aims to disrupt operations and conceal malicious emails, potentially setting the stage for further social engineering attacks. Parallels can be drawn to the use of Domain Generation Algorithm (DGA) endpoints in Command-and-Control (C2) communications, where an attacker generates new and seemingly random domains in order to mask their malicious connections and evade detection.

In an email bomb attack, threat actors typically sign up their targeted recipients to a large number of email subscription services, flooding their inboxes with indirectly subscribed content [1].

Multiple threat actors have been observed utilizing this tactic, including the Ransomware-as-a-Service (RaaS) group Black Basta, also known as Storm-1811 [1] [2].

Darktrace detection of email bombing attack

In early 2025, Darktrace detected an email bomb attack where malicious actors flooded a customer's inbox while also employing social engineering techniques, specifically voice phishing (vishing). The end goal appeared to be infiltrating the customer's network by exploiting legitimate administrative tools for malicious purposes.

The emails in these attacks often bypass traditional email security tools because they are not technically classified as spam, due to the assumption that the recipient has subscribed to the service. Darktrace / EMAIL's behavioral analysis identified the mass of unusual, albeit not inherently malicious, emails that were sent to this user as part of this email bombing attack.

Email bombing attack overview

In February 2025, Darktrace observed an email bombing attack where a user received over 150 emails from 107 unique domains in under five minutes. Each of these emails bypassed a widely used and reputable Security Email Gateway (SEG) but were detected by Darktrace / EMAIL.

Graph showing the unusual spike in unusual emails observed by Darktrace / EMAIL.
Figure 1: Graph showing the unusual spike in unusual emails observed by Darktrace / EMAIL.

The emails varied in senders, topics, and even languages, with several identified as being in German and Spanish. The most common theme in the subject line of these emails was account registration, indicating that the attacker used the victim’s address to sign up to various newsletters and subscriptions, prompting confirmation emails. Such confirmation emails are generally considered both important and low risk by email filters, meaning most traditional security tools would allow them without hesitation.

Additionally, many of the emails were sent using reputable marketing tools, such as Mailchimp’s Mandrill platform, which was used to send almost half of the observed emails, further adding to their legitimacy.

 Darktrace / EMAIL’s detection of an email being sent using the Mandrill platform.
Figure 2: Darktrace / EMAIL’s detection of an email being sent using the Mandrill platform.
Darktrace / EMAIL’s detection of a large number of unusual emails sent during a short period of time.
Figure 3: Darktrace / EMAIL’s detection of a large number of unusual emails sent during a short period of time.

While the individual emails detected were typically benign, such as the newsletter from a legitimate UK airport shown in Figure 3, the harmful aspect was the swarm effect caused by receiving many emails within a short period of time.

Traditional security tools, which analyze emails individually, often struggle to identify email bombing incidents. However, Darktrace / EMAIL recognized the unusual volume of new domain communication as suspicious. Had Darktrace / EMAIL been enabled in Autonomous Response mode, it would have automatically held any suspicious emails, preventing them from landing in the recipient’s inbox.

Example of Darktrace / EMAIL’s response to an email bombing attack taken from another customer environment.
Figure 4: Example of Darktrace / EMAIL’s response to an email bombing attack taken from another customer environment.

Following the initial email bombing, the malicious actor made multiple attempts to engage the recipient in a call using Microsoft Teams, while spoofing the organizations IT department in order to establish a sense of trust and urgency – following the spike in unusual emails the user accepted the Teams call. It was later confirmed by the customer that the attacker had also targeted over 10 additional internal users with email bombing attacks and fake IT calls.

The customer also confirmed that malicious actor successfully convinced the user to divulge their credentials with them using the Microsoft Quick Assist remote management tool. While such remote management tools are typically used for legitimate administrative purposes, malicious actors can exploit them to move laterally between systems or maintain access on target networks. When these tools have been previously observed in the network, attackers may use them to pursue their goals while evading detection, commonly known as Living-off-the-Land (LOTL).

Subsequent investigation by Darktrace’s Security Operations Centre (SOC) revealed that the recipient's device began scanning and performing reconnaissance activities shortly following the Teams call, suggesting that the user inadvertently exposed their credentials, leading to the device's compromise.

Darktrace’s Cyber AI Analyst was able to identify these activities and group them together into one incident, while also highlighting the most important stages of the attack.

Figure 5: Cyber AI Analyst investigation showing the initiation of the reconnaissance/scanning activities.

The first network-level activity observed on this device was unusual LDAP reconnaissance of the wider network environment, seemingly attempting to bind to the local directory services. Following successful authentication, the device began querying the LDAP directory for information about user and root entries. Darktrace then observed the attacker performing network reconnaissance, initiating a scan of the customer’s environment and attempting to connect to other internal devices. Finally, the malicious actor proceeded to make several SMB sessions and NTLM authentication attempts to internal devices, all of which failed.

Device event log in Darktrace / NETWORK, showing the large volume of connections attempts over port 445.
Figure 6: Device event log in Darktrace / NETWORK, showing the large volume of connections attempts over port 445.
Darktrace / NETWORK’s detection of the number of the login attempts via SMB/NTLM.
Figure 7: Darktrace / NETWORK’s detection of the number of the login attempts via SMB/NTLM.

While Darktrace’s Autonomous Response capability suggested actions to shut down this suspicious internal connectivity, the deployment was configured in Human Confirmation Mode. This meant any actions required human approval, allowing the activities to continue until the customer’s security team intervened. If Darktrace had been set to respond autonomously, it would have blocked connections to port 445 and enforced a “pattern of life” to prevent the device from deviating from expected activities, thus shutting down the suspicious scanning.

Conclusion

Email bombing attacks can pose a serious threat to individuals and organizations by overwhelming inboxes with emails in an attempt to obfuscate potentially malicious activities, like account takeovers or credential theft. While many traditional gateways struggle to keep pace with the volume of these attacks—analyzing individual emails rather than connecting them and often failing to distinguish between legitimate and malicious activity—Darktrace is able to identify and stop these sophisticated attacks without latency.

Thanks to its Self-Learning AI and Autonomous Response capabilities, Darktrace ensures that even seemingly benign email activity is not lost in the noise.

Credit to Maria Geronikolou (Cyber Analyst and SOC Shift Supervisor) and Cameron Boyd (Cyber Security Analyst), Steven Haworth (Senior Director of Threat Modeling), Ryan Traill (Analyst Content Lead)

Appendices

[1] https://www.microsoft.com/en-us/security/blog/2024/05/15/threat-actors-misusing-quick-assist-in-social-engineering-attacks-leading-to-ransomware/

[2] https://thehackernews.com/2024/12/black-basta-ransomware-evolves-with.html

Darktrace Models Alerts

Internal Reconnaissance

·      Device / Suspicious SMB Scanning Activity

·      Device / Anonymous NTLM Logins

·      Device / Network Scan

·      Device / Network Range Scan

·      Device / Suspicious Network Scan Activity

·      Device / ICMP Address Scan

·      Anomalous Connection / Large Volume of LDAP Download

·      Device / Suspicious LDAP Search Operation

·      Device / Large Number of Model Alerts

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About the author
Maria Geronikolou
Cyber Analyst

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April 11, 2025

FedRAMP High-compliant email security protects federal agencies from nation-state attacks

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What is FedRAMP High Authority to Operate (ATO)?

Federal Risk and Authorization Management Program (FedRAMP®) High is a government-wide program that promotes the adoption of secure cloud services across the federal government by providing a standardized approach to security and risk assessment for cloud technologies and federal agencies, ensuring the protection of federal information.  

Cybersecurity is paramount in the Defense Industrial Base (DIB), where protecting sensitive information and ensuring operational resilience from the most sophisticated adversaries has national security implications. Organizations within the DIB must comply with strict security standards to work with the U.S. federal government, and FedRAMP High is one of those standards.

Darktrace achieves FedRAMP High ATO across IT, OT, and email

Last week, Darktrace Federal shared that we achieved FedRAMP® High ATO, a significant milestone that recognizes our ability to serve federal customers across IT, OT, and email via secure cloud-native deployments.  

Achieving the FedRAMP High ATO indicates that Darktrace Federal has achieved the highest standard for cloud security controls and can handle the U.S. federal government’s most sensitive, unclassified data in cloud environments.

Azure Government email security with FedRAMP High ATO

Darktrace has now released Darktrace Commercial Government Cloud High/Email (DCGC High/Email). This applies our email coverage to systems hosted in Microsoft's Azure Government, which adheres to NIST SP 800-53 controls and other federal standards. DCGC High/Email both meets and exceeds the compliance requirements of the Department of Defense’s Cybersecurity Maturity Model Certification (CMMC), providing organizations with a much-needed email security solution that delivers unparalleled, AI-driven protection against sophisticated cyber threats.

In these ways, DCGC High/Email enhances compliance, security, and operational resilience for government and federally-affiliated customers. Notably, it is crucial for securing contractors and suppliers within DIB, helping those organizations implement necessary cybersecurity practices to protect Controlled Unclassified Information (CUI) and Federal Contract Information (FCI).

Adopting DCGC High/Email ensures organizations within the DIB can work with the government without needing to invest extensive time and money into meeting the strict compliance standards.

Building DCGC High/Email to ease DIB work with the government

DCGC High/Email was built to achieve FedRAMP High standards and meet the most rigorous security standards required of our customers. This level of compliance not only allows more organizations than ever to leverage our AI-driven technology, but also ensures that customer data is protected by the highest security measures available.

The DIB has never been more critical to national security, which means they are under constant threats from nation state and cyber criminals. We built DCGC High/Email to FedRAMP High controls to ensure sensitive company and federal government communications are secured at the highest level possible.” – Marcus Fowler, CEO of Darktrace Federal

Evolving threats now necessitate DCGC High/Email

According to Darktrace’s 2025 State of AI Cybersecurity report, more than half (54%) of global government cybersecurity professionals report seeing a significant impact from AI-powered cyber threats.  

These aren’t the only types of sophisticated threats. Advanced Persistent Threats (APTs) are launched by nation-states or cyber-criminal groups with the resources to coordinate and achieve long-term objectives.  

These attacks are carefully tailored to specific targets, using techniques like social engineering and spear phishing to gain initial access via the inbox. Once inside, attackers move laterally through networks, often remaining undetected for months or even years, silently gathering intelligence or preparing for a decisive strike.  

However, the barrier for entry for these threat actors has been lowered immensely, likely related to the observed impact of AI-powered cyber threats. Securing email environments is more important than ever.  

Darktrace’s 2025 State of AI Cybersecurity report also found that 89% of government cybersecurity professionals believe AI can help significantly improve their defensive capabilities.  

Darktrace's AI-powered defensive tools are uniquely capable of detecting and neutralizing APTs and other sophisticated threats, including ones that enter via the inbox. Our Self-Learning AI continuously adapts to evolving threats, providing real-time protection.

Darktrace builds to secure the DIB to the highest degree

In summary, Darktrace Federal's achievement of FedRAMP High ATO and the introduction of DCGC High/Email mark significant advancements in our ability to protect defense contractors and federal customers against sophisticated threats that other solutions miss.

For a technical review of Darktrace Federal’s Cyber AI Mission Defense™ solution, download an independent evaluation from the Technology Advancement Center here.

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About the author
Marcus Fowler
CEO of Darktrace Federal and SVP of Strategic Engagements and Threats
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