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April 28, 2021

How AI Email Security Benefits Human Defenders

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28
Apr 2021
Learn how autonomous AI frees up IT teams and allows them to focus on what matters. Say goodbye to weighed-down teams and lengthy security processes.

At the heart of any email attack is the goal of moving the recipient to engage: whether that’s clicking a link, filling in a form, or opening an attachment. And with over nine in ten cyber-attacks starting with an email, this attack vector continues to prove successful, despite organizations’ best efforts to safeguard their workforce by deploying email gateways and training employees to spot phishing attempts.

Email attackers have seen such success because they understand their victims. They know that, ultimately, human beings are creatures of habit, prone to error, and susceptible to their emotions. Years of experience has allowed attackers to fine tune their emails making them more plausible and more provocative. Automated tools are now increasing the speed and scale at which criminals can buy new domains and send emails en masse. This makes it even easier to ‘A/B test’ attack methods: abandoning those that don’t see high success rates and capitalizing on those that do.

We can classify phishing attempts into five broad categories, each aiming to trigger a different emotional reaction and elicit a response.

  • Fear: “We have detected a virus on your device, log in to your McAfee account.”
  • Curiosity: “You have 3 new voicemails, click here.”
  • Generosity: “COVID-19 has greatly impacted homelessness in your area. Donate now.”
  • Greed: “Only 23 iPhones left to give away, act now!”
  • Concern: “Coronavirus outbreak in your area: Find out more.”

It’s worth noting that today’s increasingly dynamic workforces are more susceptible to these techniques, isolated in their homes and hungry for new information.

Turning to tech

As email attacks continue to trick employees and find success, many organizations have realized that the built-in security tools that come with their email provider aren’t enough to defend against today’s attacks. Additional email gateways are successful in catching spam and other low-hanging fruit, but fail to stop advanced attacks – particularly those leveraging novel malware, new domains, or advanced techniques. These advanced attacks are also the most damaging to businesses.

This failure is due to an inherent weakness in the legacy approach of traditional security tools. They compare inbound mail against lists of ‘known bad’ IPs, domains, and file hashes. Senders and recipients are treated simply as data points – ignoring the nuances of the human beings behind the keyboards.

Looking at these metrics in isolation fails to take into account the full context that can only be gained by understanding the people behind email interactions: where they usually log in from, who they communicate with, how they write, and what types of attachments they send and receive. It is this rich, personal context that reveals seemingly benign emails to be unmistakably malicious, especially when other data fails to reveal the danger.

Misunderstanding the human

Frustrated with the ineffectiveness of traditional tools, many organizations think that the solution is to minimize the chances that employees engage with malicious emails through comprehensive employee training. Indeed, companies often attempt to train their employees to spot malicious emails to compensate for their technology’s lack of detection.

Considering humans to be the last line of defense is dangerous, and this approach overlooks the fact that today’s sophisticated fakes can appear indistinguishable to legitimate mails. It's only when you really break an email down beyond the text, beyond the personal name, beyond the domain and email address (in the case of compromised trusted senders), that you can decipher between real and fake.

Large data breaches of recent years have given attackers greater access than ever to corporate emails and stolen passwords, and so supply chain attacks are becoming increasingly common. When attackers take over a trusted account or an existing email thread, how can an employee be expected to notice a subtle change in wording or the different type of attached document? However rigorous the internal training program and regardless of how vigilant employees are, we are now at the point where humans cannot spot these very subtle indicators. And one click is all it takes.

Understanding the human

Email security, for a long time, remains an unsolved piece of the complex cyber security puzzle. The failure of both traditional tools and employee training has prompted organizations to take a radically different approach. Thousands of businesses across the world, in both the public and private sector, use artificial intelligence that understands the human behind the keyboard and forms a nuanced and continually evolving understanding of email interactions across the business.

By learning what a human does, who they interact with, how they write, and the substance of a typical conversation between any two or more people, AI begins to understand the habits of employees, and over time it builds a comprehensive picture of their normal patterns of behavior. Most importantly, AI is self-learning, continuously revising its understanding of ‘normal’ so that when employees’ habits change, so does the AI’s understanding.

This enables the technology to detect behavioral anomalies that fall outside of an employee’s ‘pattern of life’, or the pattern of life for the organization as a whole.

This fundamentally new approach to email security enables the system to recognize the subtle indicators of a threat and make accurate decisions to stop or allow emails to pass through, even if a threat has never been seen before.

Sitting behind email gateways, this self-learning technology has extremely high catch rates. It has caught countless malicious emails that other tools missed, from impersonations of senior financial personnel to ‘fearware’ that played on the workforce’s uncertainties at a time of pandemic.

Attackers are continuing to innovate, and automation has led to a new wave of email threats. 88% of security leaders now believe that cyber-attacks powered by offensive AI are inevitable. The email threat landscape is rapidly changing, and we can expect to receive more hoax emails that are more convincing. Now is a crucial moment for organizations to prepare for this eventuality by adopting AI in their email defenses.

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
Dan Fein
VP, Product

Based in New York, Dan joined Darktrace’s technical team in 2015, helping customers quickly achieve a complete and granular understanding of Darktrace’s product suite. Dan has a particular focus on Darktrace/Email, ensuring that it is effectively deployed in complex digital environments, and works closely with the development, marketing, sales, and technical teams. Dan holds a Bachelor’s degree in Computer Science from New York University.

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December 19, 2024

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Darktrace Recognized in the Gartner® Magic Quadrant™ for Email Security Platforms

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Darktrace has been recognized in the first ever Gartner Magic Quadrant for Email Security Platforms (ESP).  As a Challenger, we have been recognized based on our Ability to Execute and Completeness of Vision.

The Gartner Magic Quadrant for Email Security is designed to help organizations evaluate which email security solutions might be the best fit for their needs by providing a visual representation of the market vendors and the strengths and cautions of different vendors. We encourage our customers to read the full report to get the complete picture.

Darktrace / EMAIL has a unique AI approach to identifying threats, including NLP and behavioral analysis, instead of traditional security measures like signatures and sandboxing – providing protection against advanced attacks like Business Email Compromise (BEC) and spear phishing. We believe our AI-first approach delivers high-quality solutions that our customers trust, allowing them to stay ahead of sophisticated threats that other tools miss.  

We’re proud of Darktrace’s rapid growth, geographic scale, and ability to execute effectively in the email security market, which reflect our commitment to delivering high-quality, reliable solutions that meet the evolving needs of our customers.

What do we believe makes Darktrace the fastest growing email security solution on the market?

An AI-first approach to innovation: Catching the threats others miss

As one of the founders of the ICES category, Darktrace has a long history of innovation, backed by over 200 patents. While other email security solutions are only just starting to apply machine learning (ML) techniques to outdated methods like signature analysis, reputation lists, and sandboxing, Darktrace has redefined the approach to email threat detection with its pioneering AI-driven anomaly detection engine.

Traditional ESPs often miss advanced threats because they rely on rules and signatures that focus on payloads and blindly trust known sources. This approach requires constant updates and frequently fails to detect threats like Business Email Compromise and Spear Phishing. In contrast, Darktrace / EMAIL uses advanced anomaly detection to identify the most sophisticated threats by focusing on unusual patterns and behaviors. This innovative approach has consistently delivered superior detection, stopping on average 58% of the threats that other solutions in the security stack miss.1

But our AI-first approach doesn’t stop at the inbox. At Darktrace, we transcend the limitations of traditional email security by leveraging a platform that unifies insights across multiple domains, providing robust protection against multi-domain threats. Our award-winning solutions defend the most popular attack vectors, including email, messaging, network, and identity protection. By combining signals from all domains, we establish unique behavioral profiles for each device and user, significantly enhancing detection precision.  

This pioneering approach has led to introducing industry-first advancements like QR code analysis and automated incident investigations, alongside game-changing functionality including:

  • Microsoft Teams security with advanced messaging analysis: The ability to identify critical early phishing and insider threats across both email and Microsoft Teams messaging.  
  • AI analyst narratives for improved end user reporting: that reduces phishing investigations by 60% by exposing unique narratives that provide the context of each received email and give feedback to each employee as they interact with their mail.2
  • Mailbox Security Assistant: to perform advanced behavioral browser analysis and stop malicious links within webpages, detecting and remediating 70% more malicious phishing links than traditional tools.3  
  • AI based, autonomous data loss prevention: to immediately secure your organization from misdirected emails, insider threats, and data loss—both classified and unclassified- without any administrative overhead.

Customer trust that fuels exponential growth

With almost 5,000 customers in under 5 years, we've doubled the growth rate of other vendors in the email security market. Our rapid market penetration, fueled by customer satisfaction and pioneering technology, showcases our revolutionary approach and sets new industry standards. 

Darktrace’s exceptional customer retention is fueled by an unparalleled customer experience, extensive regional support, dedicated account teams, and cutting-edge scalable technology. We pride ourselves on having a global network with local expertise, consisting of 110 worldwide offices which provide local language and technical support to offer multilingual, in-house assistance to our customer base.

Check it out – Darktrace / EMAIL has the highest percentage of 5-star ratings with a 4.8 rating on Gartner® Peer Insights™.4

Supporting every stage of your email security journey

Darktrace / EMAIL supports your security maturity journey, from first time security buyers to mature security stacks looking to augment their existing ESPs – by handling advanced threats without extensive tuning. And unlike other solutions that create a siloed and parallel solution, it works harmoniously with native email providers to create a modern email security stack. That’s why Darktrace performs well with first-time email security buyers and has strong renewal rates.

Integrating with Microsoft and Google via API, we replace traditional Secure Email Gateways (SEGs) with a modern, comprehensive email security stack. By combining approaches, our solution merges attack-centric analysis, which learns attack patterns and threat intelligence, with a business-centric approach that understands user behavior and inbox activity to deliver a unified stack that defends the entire threat spectrum – leading Darktrace to be recognized as Microsoft Partner of the year UK 2024.  

Our user-friendly, self-learning AI solution requires minimal tuning and deployment, making it perfect for customers looking for a highly usable but lightly configurable solution that will accompany them throughout their lifetime as they mature their email security stack in line with the evolving threat landscape.

Learn more

Get complimentary access to the full Gartner® Magic Quadrant™ for Email Security Platforms here.

To learn more about Darktrace / EMAIL or to get a free demo, check out the product hub.

References

1 From September 1 – December 31 2023, 58% of the phishing emails analyzed by Darktrace / EMAIL had already passed through native spam filtering and email security controls. (Darktrace End of Year Threat Report 2023)

2 When customers deployed the Darktrace / EMAIL Outlook Add-in there was a 60% decrease in incorrectly reported phishing emails. Darktrace Internal Research, 2024

3 Once a user reports phishing that contains a link, an automated second level triage engages our link analysis infrastructure expanding the signals analyzed. Darktrace Internal Research, 2024

4 Based on 252 reviews as of 19th December 2024

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About the author
Carlos Gray
Product Manager

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December 17, 2024

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Inside the SOC

Cleo File Transfer Vulnerability: Patch Pitfalls and Darktrace’s Detection of Post-Exploitation Activities

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File transfer applications: A target for ransomware

File transfer applications have been a consistent target, particularly for ransomware groups, in recent years because they are key parts of business operations and have trusted access across different parts of an organization that include potentially confidential and personal information about an organization and its employees.

Recent targets of ransomware criminals includes applications like Acellion, Moveit, and GoAnywhere [1]. This seems to have been the case for Cleo’s managed file transfer (MFT) software solutions and the vulnerability CVE-2024-50623.

Threat overview: Understanding Cleo file transfer vulnerability

This vulnerability was believed to have been patched with the release of version 5.8.0.21 in late October 2024. However, open-source intelligence (OSINT) reported that the Clop ransomware group had managed to bypass the initial patch in late November, leading to the successful exploitation of the previously patched CVE.

In the last few days Cleo has published a new vulnerability, CVE-2024-55956, which is not a patch bypass of the CVE-2024-50623 but rather another vulnerability. This is also an unauthenticated file write vulnerability but while CVE-2024-50623 allows for both reading and writing arbitrary files, the CVE-2024-55956 only allows for writing arbitrary files and was addressed in version 5.8.0.24 [2].

Darktrace Threat Research analysts have already started investigating potential signs of devices running the Cleo software with network traffic supporting this initial hypothesis.

Comparison of CVE-2024-50623 and CVE-2024-55956

While CVE-2024-50623 was initially listed as a cross-site scripting issue, it was updated on December 10 to reflect unrestricted file upload and download. This vulnerability could lead to remote code execution (RCE) in versions of Cleo’s Harmony, VLTrader, and LexiCom products prior to 5.8.0.24. Attackers could leverage the fact that files are placed in the "autorun" sub-directory within the installation folder and are immediately read, interpreted, and evaluated by the susceptible software [3].

CVE-2024-55956, refers to an unauthenticated user who can import and execute arbitrary Bash or PowerShell commands on the host system by leveraging the default settings of the Autorun directory [4]. Both CVEs have occurred due to separate issues in the “/Synchronization” endpoint.

Investigating post exploitation patterns of activity on Cleo software

Proof of exploitation

Darktrace’s Threat Research analysts investigated multiple cases where devices identified as likely running Cleo software were detected engaging in unusual behavior. Analysts also attempted to identify any possible association between publicly available indicators of compromise (IoCs) and the exploitation of the vulnerability, using evidence of anomalous network traffic.

One case involved an Internet-facing device likely running Cleo VLTrader software (based on its hostname) reaching out to the 100% rare Lithuanian IP 181.214.147[.]164 · AS 15440 (UAB Baltnetos komunikacijos).

This activity occurred in the early hours of December 8 on the network of a customer in the energy sector. Darktrace detected a Cleo server transferring around over 500 MB of data over multiple SSL connections via port 443 to the Lithuanian IP. External research reported that this IP appears to be a callback IP observed in post-exploitation activity of vulnerable Cleo devices [3].

While this device was regularly observed sending data to external endpoints, this transfer represented a small increase in data sent to public IPs and coupled with the rarity of the destination, triggered a model alert as well as a Cyber AI Analyst Incident summarizing the transfer. Unfortunately, due to the encrypted connection no further analysis of the transmitted data was possible. However, due to the rarity of the activity, Darktrace’s Autonomous Response intervened and prevented any further connections to the IP.

 Model Alert Event Log show repeated connections to the rare IP, filtered with the rarity metric.
Figure 1: Model Alert Event Log show repeated connections to the rare IP, filtered with the rarity metric.
Shows connections to 181.214.147[.]164 and the amount of data transferred.
Figure 2: Shows connections to 181.214.147[.]164 and the amount of data transferred.

On the same day, external connections were observed to the external IP 45.182.189[.]225, along with inbound SSL connections from the same endpoint. OSINT has also linked this IP to the exploitation of Cleo software vulnerabilities [5].

Outgoing connections from a Cleo server to an anomalous endpoint.
Figure 3: Outgoing connections from a Cleo server to an anomalous endpoint.
 Incoming SSL connections from the external IP 45.182.189[.]225.
Figure 4: Incoming SSL connections from the external IP 45.182.189[.]225.

Hours after the last connection to 181.214.147[.]164, the integration detection tool from CrowdStrike, which the customer had integrated with Darktrace, issued an alert. This alert provided additional visibility into host-level processes and highlighted the following command executed on the Cleo server:

“D:\VLTrader\jre\bin\java.exe" -jar cleo.4889

Figure 5: The executed comand “D:\VLTrader\jre\bin\java.exe" -jar cleo.4889 and the Resource Location: \Device\HarddiskVolume3\VLTrader\jre\bin\java.exe.

Three days later, on December 11, another CrowdStrike integration alert was generated, this time following encoded PowerShell command activity on the server. This is consistent with post-exploitation activity where arbitrary PowerShell commands are executed on compromised systems leveraging the default settings of the Autorun directory, as highlighted by Cleo support [6]. According to external researchers , this process initiates connections to an external IP to retrieve JAR files with webshell-like functionality for continued post-exploitation [3]. The IP embedded in both commands observed by Darktrace was 38.180.242[.]122, hosted on ASN 58061(Scalaxy B.V.). There is no OSINT associating this IP with Cleo vulnerability exploitation at the time of writing.

Another device within the same customer network exhibited similar data transfer and command execution activity around the same time, suggesting it had also been compromised through this vulnerability. However, this second device contacted a different external IP, 5.45.74[.]137, hosted on AS 58061 (Scalaxy B.V.).

Like the first device, multiple connections to this IP were detected, with almost 600 MB of data transferred over the SSL protocol.

The Security Integration Detection Model that was triggered  and the PowerShell command observed
Figure 6: The Security Integration Detection Model that was triggered  and the PowerShell command observed
 Incoming connections from the external IP 38.180.242[.]122.
Figure 7: Incoming connections from the external IP 38.180.242[.]122.
Connections to the external IP 5.45.74[.]137.
Figure 8: Connections to the external IP 5.45.74[.]137.
Figure 9: Autonomous Response Actions triggered during the suspicious activities

While investigating potential Cleo servers involved in similar outgoing data activity, Darktrace’s Threat Research team identified two additional instances of likely Cleo vulnerability exploitation used to exfiltrate data outside the network. In those two instances, unusual outgoing data transfers were observed to the IP 176.123.4[.]22 (AS 200019, AlexHost SRL), with around 500 MB of data being exfiltrated over port 443 in one case (the exact volume could not be confirmed in the other instance). This IP was found embedded in encoded PowerShell commands examined by external researchers in the context of Cleo vulnerability exploitation investigations.

Conclusion

Overall, Cleo software represents a critical component of many business operations, being utilized by over 4,000 organizations worldwide. This renders the software an attractive target for threat actors who aim at exploiting internet-facing devices that could be used to compromise the software’s direct users but also other dependent industries resulting in supply chain attacks.

Darktrace / NETWORK was able to capture traffic linked to exploitation of CVE-2024-50623 within models that triggered such as Unusual Activity / Unusual External Data to New Endpoint while its Autonomous Response capability successfully blocked the anomalous connections and exfiltration attempts.

Information on new CVEs, how they're being exploited, and whether they've been patched can be fast-changing, sometimes limited and often confusing. Regardless, Darktrace is able to identify and alert to unusual behavior on these systems, indicating exploitation.

Credit to Maria Geronikolou, Alexandra Sentenac, Emma Fougler, Signe Zaharka and the Darktrace Threat Research team

Insights from Darktrace’s First 6: Half-year threat report for 2024

First 6: half year threat report darktrace screenshot

Darktrace’s First 6: Half-Year Threat Report 2024 highlights the latest attack trends and key threats observed by the Darktrace Threat Research team in the first six months of 2024.

  • Focuses on anomaly detection and behavioral analysis to identify threats
  • Maps mitigated cases to known, publicly attributed threats for deeper context
  • Offers guidance on improving security posture to defend against persistent threats

Appendices

References

[1] https://blog.httpcs.com/en/file-sharing-and-transfer-software-the-new-target-of-hackers/

[2] https://attackerkb.com/topics/geR0H8dgrE/cve-2024-55956/rapid7-analysis

[3] https://www.huntress.com/blog/threat-advisory-oh-no-cleo-cleo-software-actively-being-exploited-in-the-wild

[4] https://nvd.nist.gov/vuln/detail/CVE-2024-55956

[5] https://arcticwolf.com/resources/blog/cleopatras-shadow-a-mass-exploitation-campaign/

[6] https://support.cleo.com/hc/en-us/articles/28408134019735-Cleo-Product-Security-Advisory-CVE-Pending

[7] https://support.cleo.com/hc/en-us/articles/360034260293-Local-HTTP-Users-Configuration

Darktrace Model Alerts

Anomalous Connection / Data Sent to Rare Domain

Unusual Activity / Unusual External Data to New Endpoint

Unusual Activity / Unusual External Data Transfer

Device / Internet Facing Device with High Priority Alert

Anomalous Server Activity / Rare External from Server

Anomalous Connection / New User Agent to IP Without Hostname

Security Integration / High Severity Integration Incident

Security Integration / Low Severity Integration Detection

Autonomous Response Model Detections

Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

Cyber AI Analyst Incidents

Unusual External Data Transfer

MITRE ATT&CK Mapping

Tactic – Technique

INITIAL ACCESS – Exploit Public-Facing Application

COMMAND AND CONTROL – Application Layer Protocol (Web Protocols)

COMMAND AND CONTROL – Encrypted Channel

PERSISTENCE – Web Shell

EXFILTRATION - Exfiltration Over C2 Channel

IoC List

IoC       Type    Description + Probability

181.214.147[.]164      IP Address       Likely C2 Infrastructure

176.123.4[.]22            IP Address       Likely C2 Infrastructure

5.45.74[.]137               IP Address           Possible C2 Infrastructure

38.180.242[.]122        IP Address       Possible C2 Infrastructure

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About the author
Maria Geronikolou
Cyber Analyst
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