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April 1, 2023

Cyber Security Threats - Email Compromise With Generative AI

Discover how generative AI is impacting email attacks and what companies can do to prepare for more sophisticated and targeted attacker campaigns.
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
Max Heinemeyer
Global Field CISO
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01
Apr 2023

Email communications in the era of generative AI

Today’s headlines on cyber security attacks are dominated by serious breaches that cripple critical national infrastructure providers, wreak geopolitical havoc through nation state espionage, and create paralyzing financial demands through extortion and ransomware. But how do these breaches occur in the first place, and why do they keep happening?

Social engineering – specifically malicious cyber campaigns delivered via email - remain the primary source of an organization’s vulnerability to attack. A recent survey conducted by Darktrace to 6,700 global cross-industry professionals across the UK, US, Australia, France, Germany, and Netherlands, found almost a third (30%) have fallen victim to a fraudulent email. The risk, as ever, seems to be uncontrollably on the rise – 70% of respondents have noticed an increase in the frequency of malicious emails in the last six months. 

At the end of last year, I wrote about how widespread accessibility to generative AI has compounded the problem, leading to likely efficiency gains for skilled threat actors launching email attacks. Just a few weeks ago, we published research which demonstrated that while the number of email attacks across our own customer base has remained steady since ChatGPT’s release, those that rely on tricking victims into clicking malicious links have declined, while linguistic complexity, including text volume, punctuation, and sentence length among others, have increased. This indicates that cyber-criminals may be redirecting their focus to crafting more sophisticated social engineering scams that exploit user trust delivered over email. 

Our latest findings, conducted by Darktrace Research, today reveal a 135% increase in ‘novel social engineering attacks’ across thousands of active Darktrace/Email customers from January to February 2023, corresponding with the widespread adoption of ChatGPT. A novel social engineering phishing email is an email attack that shows a strong linguistic deviation – semantically and syntactically – compared to other phishing emails. The trend suggests that generative AI, such as ChatGPT, is providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale.

Organizations are already well aware of the danger novel threats pose – globally, 82% of respondents reported are concerned that hackers can use generative AI to create scam emails that are indistinguishable from genuine communication.

Navigating the trust deficit 

Employees are being exploited continuously through their primary means of communication - email. Given that humans, and our psychology, are at the heart of the problem, organizations have scrambled to develop awareness and training programs that are delivered routinely to employees in an attempt to help them defend themselves and their organization. While a defense-in-depth approach is generally a good practice to follow, the value of security awareness training, teaching employees to spot attempts at social engineering delivered in text format, is diminishing rapidly. This problem has become especially evident now that we find ourselves in a world where ‘bad’ emails look all but undistinguishable to the human eye from ‘good’ emails. 

Over emphasizing the responsibility of employees poses a business challenge as well as a security problem: a bloated trust deficit. In times of economic uncertainty, business success is predicated on employee productivity, creativity, and efficiency. All three of these are squashed when employees treat the communication they receive, both internal and external, with forensic suspicion and mistrust. 

As generative AI becomes more mainstream – across images, audio, video, and text – we anticipate that this erosion of trust in digital communication will only continue. What happens to the workplace if an employee is left questioning their own perception when communicating with their manager or a colleague, who they can see and hear over a video conference call, but who may be an entirely fictitious creation?

The way forward

The future lies in a partnership between artificial intelligence and human beings where the algorithms are responsible for determining whether communication is malicious or benign, thereby taking the burden of responsibility off the human. In turn, humans can pursue activities that drive productivity and performance. Current training and awareness programs, coupled with traditional email security technologies which assume that knowledge of past attacks will help predict campaigns, are not sustainable in this rapidly evolving landscape. 

Our research reveals that traditional email security tools that rely on knowledge of past threats, take an average of thirteen days from an attack being launched on a victim to that attack being detected. This leaves defenders vulnerable for almost two weeks if they rely solely on traditional tools. When this statistic is contextualized against the 135% increase we’ve seen in novel social engineering campaigns, the inefficiency of ‘attack centric’ email security is made perfectly evident. If we don’t know how to define entirely new and unique attacks, how can we ever hope to recognize them based on past attacks? 

A deep understanding of ‘you’ is needed in the face of these radical changes to the email threat landscape. Instead of trying to predict attacks, an understanding of your employees’ behavior, based from their email inbox, is needed to create patterns of life for every email user: their relationships, tone and sentiments and hundreds of other data points. By leveraging AI to combat email security threats, we not only reduce risk, but revitalize organizational trusts and contribute to business outcomes.

Ironically, generative AI may be worsening the social engineering challenge, but AI that knows you, could be the parry. 

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
Max Heinemeyer
Global Field CISO

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April 10, 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 recipients, 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 Access 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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