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April 1, 2023
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Cyber Security Threats - Email Compromise With Generative AI

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

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.
Author
Max Heinemeyer
Chief Product Officer

Max is a cyber security expert with over a decade of experience in the field, specializing in a wide range of areas such as Penetration Testing, Red-Teaming, SIEM and SOC consulting and hunting Advanced Persistent Threat (APT) groups. At Darktrace, Max is closely involved with Darktrace’s strategic customers & prospects. He works with the R&D team at Darktrace, shaping research into new AI innovations and their various defensive and offensive applications. Max’s insights are regularly featured in international media outlets such as the BBC, Forbes and WIRED. Max holds an MSc from the University of Duisburg-Essen and a BSc from the Cooperative State University Stuttgart in International Business Information Systems.

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October 4, 2024

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Inside the SOC

From Call to Compromise: Darktrace’s Response to a Vishing-Induced Network Attack

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What is vishing?

Vishing, or voice phishing, is a type of cyber-attack that utilizes telephone devices to deceive targets. Threat actors typically use social engineering tactics to convince targets that they can be trusted, for example, by masquerading as a family member, their bank, or trusted a government entity. One method frequently used by vishing actors is to intimidate their targets, convincing them that they may face monetary fines or jail time if they do not provide sensitive information.

What makes vishing attacks dangerous to organizations?

Vishing attacks utilize social engineering tactics that exploit human psychology and emotion. Threat actors often impersonate trusted entities and can make it appear as though a call is coming from a reputable or known source.  These actors often target organizations, specifically their employees, and pressure them to obtain sensitive corporate data, such as privileged credentials, by creating a sense of urgency, intimidation or fear. Corporate credentials can then be used to gain unauthorized access to an organization’s network, often bypassing traditional security measures and human security teams.

Darktrace’s coverage of vishing attack

On August 12, 2024, Darktrace / NETWORK identified malicious activity on the network of a customer in the hospitality sector. The customer later confirmed that a threat actor had gained unauthorized access through a vishing attack. The attacker successfully spoofed the IT support phone number and called a remote employee, eventually leading to the compromise.

Figure 1: Timeline of events in the kill chain of this attack.

Establishing a Foothold

During the call, the remote employee was requested to authenticate via multi-factor authentication (MFA). Believing the caller to be a member of their internal IT support, using the legitimate caller ID, the remote user followed the instructions and confirmed the MFA prompt, providing access to the customer’s network.

This authentication allowed the threat actor to login into the customer’s environment by proxying through their Virtual Private Network (VPN) and gain a foothold in the network. As remote users are assigned the same static IP address when connecting to the corporate environment, the malicious actor appeared on the network using the correct username and IP address. While this stealthy activity might have evaded traditional security tools and human security teams, Darktrace’s anomaly-based threat detection identified an unusual login from a different hostname by analyzing NTLM requests from the static IP address, which it determined to be anomalous.

Observed Activity

  • On 2024-08-12 the static IP was observed using a credential belonging to the remote user to initiate an SMB session with an internal domain controller, where the authentication method NTLM was used
  • A different hostname from the usual hostname associated with this remote user was identified in the NTLM authentication request sent from a device with the static IP address to the domain controller
  • This device does not appear to have been seen on the network prior to this event.

Darktrace, therefore, recognized that this login was likely made by a malicious actor.

Internal Reconnaissance

Darktrace subsequently observed the malicious actor performing a series of reconnaissance activities, including LDAP reconnaissance, device hostname reconnaissance, and port scanning:

  • The affected device made a 53-second-long LDAP connection to another internal domain controller. During this connection, the device obtained data about internal Active Directory (AD) accounts, including the AD account of the remote user
  • The device made HTTP GET requests (e.g., HTTP GET requests with the Target URI ‘/nice ports,/Trinity.txt.bak’), indicative of Nmap usage
  • The device started making reverse DNS lookups for internal IP addresses.
Figure 2: Model alert showing the IP address from which the malicious actor connected and performed network scanning activities via port 9401.
Figure 3: Model Alert Event Log showing the affected device connecting to multiple internal locations via port 9401.

Lateral Movement

The threat actor was also seen making numerous failed NTLM authentication requests using a generic default Windows credential, indicating an attempt to brute force and laterally move through the network. During this activity, Darktrace identified that the device was using a different hostname than the one typically used by the remote employee.

Cyber AI Analyst

In addition to the detection by Darktrace / NETWORK, Darktrace’s Cyber AI Analyst launched an autonomous investigation into the ongoing activity. The investigation was able to correlate the seemingly separate events together into a broader incident, continuously adding new suspicious linked activities as they occurred.

Figure 4: Cyber AI Analyst investigation showing the activity timeline, and the activities associated with the incident.

Upon completing the investigation, Cyber AI Analyst provided the customer with a comprehensive summary of the various attack phases detected by Darktrace and the associated incidents. This clear presentation enabled the customer to gain full visibility into the compromise and understand the activities that constituted the attack.

Figure 5: Cyber AI Analyst displaying the observed attack phases and associated model alerts.

Darktrace Autonomous Response

Despite the sophisticated techniques and social engineering tactics used by the attacker to bypass the customer’s human security team and existing security stack, Darktrace’s AI-driven approach prevented the malicious actor from continuing their activities and causing more harm.

Darktrace’s Autonomous Response technology is able to enforce a pattern of life based on what is ‘normal’ and learned for the environment. If activity is detected that represents a deviation from expected activity from, a model alert is triggered. When Darktrace’s Autonomous Response functionality is configured in autonomous response mode, as was the case with the customer, it swiftly applies response actions to devices and users without the need for a system administrator or security analyst to perform any actions.

In this instance, Darktrace applied a number of mitigative actions on the remote user, containing most of the activity as soon as it was detected:

  • Block all outgoing traffic
  • Enforce pattern of life
  • Block all connections to port 445 (SMB)
  • Block all connections to port 9401
Figure 6: Darktrace’s Autonomous Response actions showing the actions taken in response to the observed activity, including blocking all outgoing traffic or enforcing the pattern of life.

Conclusion

This vishing attack underscores the significant risks remote employees face and the critical need for companies to address vishing threats to prevent network compromises. The remote employee in this instance was deceived by a malicious actor who spoofed the phone number of internal IT Support and convinced the employee to perform approve an MFA request. This sophisticated social engineering tactic allowed the attacker to proxy through the customer’s VPN, making the malicious activity appear legitimate due to the use of static IP addresses.

Despite the stealthy attempts to perform malicious activities on the network, Darktrace’s focus on anomaly detection enabled it to swiftly identify and analyze the suspicious behavior. This led to the prompt determination of the activity as malicious and the subsequent blocking of the malicious actor to prevent further escalation.

While the exact motivation of the threat actor in this case remains unclear, the 2023 cyber-attack on MGM Resorts serves as a stark illustration of the potential consequences of such threats. MGM Resorts experienced significant disruptions and data breaches following a similar vishing attack, resulting in financial and reputational damage [1]. If the attack on the customer had not been detected, they too could have faced sensitive data loss and major business disruptions. This incident underscores the critical importance of robust security measures and vigilant monitoring to protect against sophisticated cyber threats.

Credit to Rajendra Rushanth (Cyber Security Analyst) and Ryan Traill (Threat Content Lead)

Appendices

Darktrace Model Detections

  • Device / Unusual LDAP Bind and Search Activity
  • Device / Attack and Recon Tools
  • Device / Network Range Scan
  • Device / Suspicious SMB Scanning Activity
  • Device / RDP Scan
  • Device / UDP Enumeration
  • Device / Large Number of Model Breaches
  • Device / Network Scan
  • Device / Multiple Lateral Movement Model Breaches (Enhanced Monitoring)
  • Device / Reverse DNS Sweep
  • Device / SMB Session Brute Force (Non-Admin)

List of Indicators of Compromise (IoCs)

IoC - Type – Description

/nice ports,/Trinity.txt.bak - URI – Unusual Nmap Usage

MITRE ATT&CK Mapping

Tactic – ID – Technique

INITIAL ACCESS – T1200 – Hardware Additions

DISCOVERY – T1046 – Network Service Scanning

DISCOVERY – T1482 – Domain Trust Discovery

RECONNAISSANCE – T1590 – IP Addresses

T1590.002 – DNS

T1590.005 – IP Addresses

RECONNAISSANCE – T1592 – Client Configurations

T1592.004 – Client Configurations

RECONNAISSANCE – T1595 – Scanning IP Blocks

T1595.001 – Scanning IP Blocks

T1595.002 – Vulnerability Scanning

References

[1] https://www.bleepingcomputer.com/news/security/securing-helpdesks-from-hackers-what-we-can-learn-from-the-mgm-breach/

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About the author
Rajendra Rushanth
Cyber Analyst

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October 3, 2024

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Cloud

Introducing real-time multi-cloud detection & response powered by AI

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We are delighted to announce the general availability of Microsoft Azure support for Darktrace / CLOUD, enabling real-time cloud detection and response across dynamic multi-cloud environments. Built on Self-Learning AI, Darktrace / CLOUD leverages Microsoft’s new virtual network flow logs (VNet flow) to offer an agentless-first approach that dramatically simplifies detection and response within Azure, unifying cloud-native security with Darktrace’s innovative ActiveAI Security Platform.

As organizations increasingly adopt multi-cloud architectures, the need for advanced, real-time threat detection and response is critical to keep pace with evolving cloud threats. Security teams face significant challenges, including increased complexity, limited visibility, and siloed tools. The dynamic nature of multi-cloud environments introduces ever-changing blind spots, while traditional security tools struggle to provide real-time insights, often offering static snapshots of risk. Additionally, cloud security teams frequently operate in isolation from SOC teams, leading to fragmented visibility and delayed responses. This lack of coordination, especially in hybrid environments, hinders effective threat detection and response. Compounding these challenges, current security solutions are split between agent-based and agentless approaches, with agentless solutions often lacking real-time awareness and agent-based options adding complexity and scalability concerns. Darktrace / CLOUD helps to solve these challenges with real-time detection and response designed specifically for dynamic cloud environments like Azure and AWS.

Pioneering AI-led real-time cloud detection & response

Darktrace has been at the forefront of real-time detection and response for over a decade, continually pushing the boundaries of AI-driven cybersecurity. Our Self-Learning AI uniquely positions Darktrace with the ability to automatically understand and instantly adapt to changing cloud environments. This is critical in today’s landscape, where cloud infrastructures are highly dynamic and ever-changing.  

Built on years of market-leading network visibility, Darktrace / CLOUD understands ‘normal’ for your unique business across clouds and networks to instantly reveal known, unknown, and novel cloud threats with confidence. Darktrace Self-Learning AI continuously monitors activity across cloud assets, containers, and users, and correlates it with detailed identity and network context to rapidly detect malicious activity. Platform-native identity and network monitoring capabilities allow Darktrace / CLOUD to deeply understand normal patterns of life for every user and device, enabling instant, precise and proportionate response to abnormal behavior - without business disruption.

Leveraging platform-native Autonomous Response, AI-driven behavioral containment neutralizes malicious activity with surgical accuracy while preventing disruption to cloud infrastructure or services. As malicious behavior escalates, Darktrace correlates thousands of data points to identify and instantly respond to unusual activity by blocking specific connections and enforcing normal behavior.

Figure 1: AI-driven behavioral containment neutralizes malicious activity with surgical accuracy while preventing disruption to cloud infrastructure or services.

Unparalleled agentless visibility into Azure

As a long-term trusted partner of Microsoft, Darktrace leverages Azure VNet flow logs to provide agentless, high-fidelity visibility into cloud environments, ensuring comprehensive monitoring without disrupting workflows. By integrating seamlessly with Azure, Darktrace / CLOUD continues to push the envelope of innovation in cloud security. Our Self-learning AI not only improves the detection of traditional and novel threats, but also enhances real-time response capabilities and demonstrates our commitment to delivering cutting-edge, AI-powered multi-cloud security solutions.

  • Integration with Microsoft Virtual network flow logs for enhanced visibility
    Darktrace / CLOUD integrates seamlessly with Azure to provide agentless, high-fidelity visibility into cloud environments. VNet flow logs capture critical network traffic data, allowing Darktrace to monitor Azure workloads in real time without disrupting existing workflows. This integration significantly reduces deployment time by 95%1 and cloud security operational costs by up to 80%2 compared to traditional agent-based solutions. Organizations benefit from enhanced visibility across dynamic cloud infrastructures, scaling security measures effortlessly while minimizing blind spots, particularly in ephemeral resources or serverless functions.
  • High-fidelity agentless deployment
    Agentless deployment allows security teams to monitor and secure cloud environments without installing software agents on individual workloads. By using cloud-native APIs like AWS VPC flow logs or Azure VNet flow logs, security teams can quickly deploy and scale security measures across dynamic, multi-cloud environments without the complexity and performance overhead of agents. This approach delivers real-time insights, improving incident detection and response while reducing disruptions. For organizations, agentless visibility simplifies cloud security management, lowers operational costs, and minimizes blind spots, especially in ephemeral resources or serverless functions.
  • Real-time visibility into cloud assets and architectures
    With real-time Cloud Asset Enumeration and Dynamic Architecture Modeling, Darktrace / CLOUD generates up-to-date architecture diagrams, giving SecOps and DevOps teams a unified view of cloud infrastructures. This shared context enhances collaboration and accelerates threat detection and response, especially in complex environments like Kubernetes. Additionally, Cyber AI Analyst automates the investigation process, correlating data across networks, identities, and cloud assets to save security teams valuable time, ensuring continuous protection and efficient cloud migrations.
Figure 2: Real-time visibility into Azure assets and architectures built from network, configuration and identity and access roles.

Unified multi-cloud security at scale

As organizations increasingly adopt multi-cloud strategies, the complexity of managing security across different cloud providers introduces gaps in visibility. Darktrace / CLOUD simplifies this by offering agentless, real-time monitoring across multi-cloud environments. Building on our innovative approach to securing AWS environments, our customers can now take full advantage of robust real-time detection and response capabilities for Azure. Darktrace is one of the first vendors to leverage Microsoft’s virtual network flow logs to provide agentless deployment in Azure, enabling unparalleled visibility without the need for installing agents. In addition, Darktrace / CLOUD offers automated Cloud Security Posture Management (CSPM) that continuously assesses cloud configurations against industry standards.  Security teams can identify and prioritize misconfigurations, vulnerabilities, and policy violations in real-time. These capabilities give security teams a complete, live understanding of their cloud environments and help them focus their limited time and resources where they are needed most.

This approach offers seamless integration into existing workflows, reducing configuration efforts and enabling fast, flexible deployment across cloud environments. By extending its capabilities across multiple clouds, Darktrace / CLOUD ensures that no blind spots are left uncovered, providing holistic, multi-cloud security that scales effortlessly with your cloud infrastructure. diagrams, visualizes cloud assets, and prioritizes risks across cloud environments.

Figure 3: Unified view of AWS and Azure cloud posture and compliance over time.

The future of cloud security: Real-time defense in an unpredictable world

Darktrace / CLOUD’s support for Microsoft Azure, powered by Self-Learning AI and agentless deployment, sets a new standard in multi-cloud security. With real-time detection and autonomous response, organizations can confidently secure their Azure environments, leveraging innovation to stay ahead of the constantly evolving threat landscape. By combining Azure VNet flow logs with Darktrace’s AI-driven platform, we can provide customers with a unified, intelligent solution that transforms how security is managed across the cloud.

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References

1. Based on internal research and customer data

2. Based on internal research

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About the author
Adam Stevens
Director of Product, Cloud Security
Your data. Our AI.
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