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November 27, 2024

Behind the Veil: Darktrace's Detection of VPN Exploitation in SaaS Environments

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27
Nov 2024
A recent phishing attack compromised an internal email account, but Darktrace’s advanced AI quickly intervened. By identifying unusual activity across email and SaaS environments, Darktrace uncovered the attacker’s use of VPNs to mask their location and shut down the threat.

Introduction

In today’s digital landscape, Software-as-a-Service (SaaS) platforms have become indispensable for businesses, offering unparalleled flexibly, scalability, and accessibly across locations. However, this convenience comes with a significant caveat - an expanded attack surface that cyber criminals are increasingly exploiting. In 2023, 96.7% of organizations reported security incidents involving at least one SaaS application [1].

Virtual private networks (VPNs) play a crucial role in SaaS security, acting as gateways for secure remote access and safeguarding sensitive data and systems when properly configured. However, vulnerabilities in VPNs can create openings for attacks to exploit, allowing them to infiltrate SaaS environments, compromise data, and disrupt business operations. Notably, in early 2024, the Darktrace Threat Research team investigated the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPNs, which would allow threat actors to gain access to sensitive systems and execute remote code.

More recently, in August, Darktrace identified a SaaS compromise where a threat actor logged into a customer’s VPN from an unusual IP address, following an initial email compromise. The attacker then used a separate VPN to create a new email rule designed to obfuscate the phishing campaign they would later launch.

Attack Overview

The initial attack vector in this case appeared to be through the customer’s email environment. A trusted external contact received a malicious email from another mutual contact who had been compromised and forwarded it to several of the organization’s employees, believing it to be legitimate. Attackers often send malicious emails from compromised accounts to their past contacts, leveraging the trust associated with familiar email addresses. In this case, that trust caused an external victim to unknowingly propagate the attack further. Unfortunately, an internal user then interacted with a malicious payload included in the reply section of the forwarded email.

Later the same day, Darktrace / IDENTITY detected unusual login attempts from the IP 5.62.57[.]7, which had never been accessed by other SaaS users before. There were two failed attempts prior to the successful logins, with the error messages “Authentication failed due to flow token expired” and “This occurred due to 'Keep me signed in' interrupt when the user was signing in.” These failed attempts indicate that the threat actor may have been attempting to gain unauthorized access using stolen credentials or exploiting session management vulnerabilities. Furthermore, there was no attempt to use multi-factor authentication (MFA) during the successful login, suggesting that the threat actor had compromised the account’s credentials.

Following this, Darktrace detected the now compromised account creating a new email rule named “.” – a telltale sign of a malicious actor attempting to hide behind an ambiguous or generic rule name.

The email rule itself was designed to archive incoming emails and mark them as read, effectively hiding them from the user’s immediate view. By moving emails to the “Archive” folder, which is not frequently checked by end users, the attacker can conceal malicious communications and avoid detection. The settings also prevent any automatic deletion of the rules or forced overrides, indicating a cautious approach to maintaining control over the mailbox without raising suspicion. This technique allows the attacker to manipulate email visibility while maintaining a façade of normality in the compromised account.

Email Rule:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: .
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace further identified that this email rule had been created from another IP address, 95.142.124[.]42, this time located in Canada. Open-source intelligence (OSINT) sources indicated this endpoint may have been malicious [2].

Given that this new email rule was created just three minutes after the initial login from a different IP in a different country, Darktrace recognized a geographic inconsistency. By analyzing the timing and rarity of the involved IP addresses, Darktrace identified the likelihood of malicious activity rather than legitimate user behavior, prompting further investigation.

Figure 1: The compromised SaaS account making anomalous login attempts from an unusual IP address in the US, followed by the creation of a new email rule from another VPN IP in Canada.

Just one minute later, Darktrace observed the attacker sending a large number of phishing emails to both internal and external recipients.

Figure 2: The compromised SaaS user account sending a high volume of outbound emails to new recipients or containing suspicious content.

Darktrace / EMAIL detected a significant spike in inbound emails for the compromised account, likely indicating replies to phishing emails.

Figure 3: The figure demonstrates the spike in inbound emails detected for the compromised account, including phishing-related replies.

Furthermore, Darktrace identified that these phishing emails contained a malicious DocSend link. While docsend[.]com is generally recognized as a legitimate file-sharing service belonging to Dropbox, it can be vulnerable to exploitation for hosting malicious content. In this instance, the DocSend domain in question, ‘hxxps://docsend[.]com/view/h9t85su8njxtugmq’, was flagged as malicious by various OSINT vendors [3][4].

Figure 4: Phishing emails detected containing a malicious DocSend link.

In this case, Darktrace Autonomous Response was not in active mode in the customer’s environment, which allowed the compromise to escalate until their security team intervened based on Darktrace’s alerts. Had Autonomous Response been enabled during the incident, it could have quickly mitigated the threat by disabling users and inbox rules, as suggested by Darktrace as actions that could be manually applied, exhibiting unusual behavior within the customer’s SaaS environment.

Figure 5: Suggested Autonomous Response actions for this incident that required human confirmation.

Despite this, Darktrace’s Managed Threat Detection service promptly alerted the Security Operations Center (SOC) team about the compromise, allowing them to conduct a thorough investigation and inform the customer before any further damage could take place.

Conclusion

This incident highlights the role of Darktrace in enhancing cyber security through its advanced AI capabilities. By detecting the initial phishing email and tracking the threat actor's actions across the SaaS environment, Darktrace effectively identified the threat and brought it to the attention of the customer’s security team.

Darktrace’s proactive monitoring was crucial in recognizing the unusual behavior of the compromised account. Darktrace / IDENTITY detected unauthorized access attempts from rare IP addresses, revealing the attacker’s use of a VPN to hide their location.

Correlating these anomalies allowed Darktrace to prompt immediate investigation, showcasing its ability to identify malicious activities that traditional security tools might miss. By leveraging AI-driven insights, organizations can strengthen their defense posture and prevent further exploitation of compromised accounts.

Credit to Priya Thapa (Cyber Analyst), Ben Atkins (Senior Model Developer) and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Models

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compromise / High Priority New Email Rule
  • SaaS / Compromise / New Email Rule and Unusual Email Activity
  • SaaS / Compromise / Unusual Login and Outbound Email Spam
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
  • SaaS / Email Nexus / Possible Outbound Email Spam

Autonomous Response Models

  • Antigena / SaaS / Antigena Email Rule Block
  • Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Technique Name Tactic ID Sub-Technique of

  • Cloud Accounts. DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS T1078.004 T1078
  • Compromise Accounts RESOURCE DEVELOPMENT T1586
  • Email Accounts RESOURCE DEVELOPMENT T1586.002 T1586
  • Internal Spearphishing LATERAL MOVEMENT T1534 -
  • Outlook Rules PERSISTENCE T1137.005 T1137
  • Phishing INITIAL ACCESS T1566 -

Indicators of Compromise (IoCs)

IoC – Type – Description

5.62.57[.]7 – Unusual Login Source

95.142.124[.]42– IP – Unusual Source for Email Rule

hxxps://docsend[.]com/view/h9t85su8njxtugmq - Domain - Phishing Link

References

[1] https://wing.security/wp-content/uploads/2024/02/2024-State-of-SaaS-Report-Wing-Security.pdf

[2] https://www.virustotal.com/gui/ip-address/95.142.124.42

[3] https://urlscan.io/result/0caf3eee-9275-4cda-a28f-6d3c6c3c1039/

[4] https://www.virustotal.com/gui/url/8631f8004ee000b3f74461e5060e6972759c8d38ea8c359d85da9014101daddb

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.
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Priya Thapa
Cyber Analyst
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March 28, 2025

Darktrace Recognized as the Only Visionary in the 2025 Gartner® Magic Quadrant™ for CPS Protection Platforms

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We are thrilled to announce that Darktrace has been named the only Visionary in the inaugural Gartner® Magic Quadrant™ for Cyber-Physical Systems (CPS) Protection Platforms. We feel This recognition highlights Darktrace’s AI-driven approach to securing industrial environments, where conventional security solutions struggle to keep pace with increasing cyber threats.

A milestone for CPS security

It's our opinion that the first-ever Gartner Magic Quadrant for CPS Protection Platforms reflects a growing industry shift toward purpose-built security solutions for critical infrastructure. As organizations integrate IT, OT, and cloud-connected systems, the cyber risk landscape continues to expand. Gartner evaluated 17 vendors based on their Ability to Execute and Completeness of Vision, establishing a benchmark for security leaders looking to enhance cyber resilience in industrial environments.

We believe the Gartner recognition of Darktrace as the only Visionary reaffirms the platform’s ability to proactively defend against cyber risks through AI-driven anomaly detection, autonomous response, and risk-based security strategies. With increasingly sophisticated attacks targeting industrial control systems, organizations need a solution that continuously evolves to defend against both known and unknown threats.

AI-driven security for CPS environments

Securing CPS environments requires an approach that adapts to the dynamic nature of industrial operations. Traditional security tools rely on static signatures and predefined rules, leaving gaps in protection against novel and sophisticated threats. Darktrace / OT takes a different approach, leveraging Self-Learning AI to detect and neutralize threats in real time, even in air-gapped or highly regulated environments.

Darktrace / OT continuously analyzes network behaviors to establish a deep understanding of what is “normal” for each industrial environment. This enables it to autonomously identify deviations that signal potential cyber threats, providing early warning and proactive defense before attacks can disrupt operations. Unlike rule-based security models that require constant manual updates, Darktrace / OT improves with the environment, ensuring long-term resilience against emerging cyber risks.

Bridging the IT-OT security gap

A major challenge for organizations protecting CPS environments is the disconnect between IT and OT security. While IT security has traditionally focused on data

protection and compliance, OT security is driven by operational uptime and safety, leading to siloed security programs that leave critical gaps in visibility and response.

Darktrace / OT eliminates these silos by providing unified visibility across IT, OT, and IoT assets, ensuring that security teams have a complete picture of their attack surface. Its AI-driven approach enables cross-domain threat detection, recognizing risks that move laterally between IT and OT environments. By seamlessly integrating with existing security architectures, Darktrace / OT helps organizations close security gaps without disrupting industrial processes.

Proactive OT risk management and resilience

Beyond detection and response, Darktrace / OT strengthens organizations’ ability to manage cyber risk proactively. By mapping vulnerabilities to real-world attack paths, it prioritizes remediation actions based on actual exploitability and business impact, rather than relying on isolated CVE scores. This risk-based approach enables security teams to focus resources where they matter most, reducing overall exposure to cyber threats.

With autonomous threat response capabilities, Darktrace / OT not only identifies risks but also contains them in real time, preventing attackers from escalating intrusions. Whether mitigating ransomware, insider threats, or sophisticated nation-state attacks, Darktrace / OT ensures that industrial environments remain secure, operational, and resilient, no matter how threats evolve.

AI-powered incident response and SOC automation

Security teams are facing an overwhelming volume of alerts, making it difficult to prioritize threats and respond effectively. Darktrace / OT’s Cyber AI Analyst acts as a force multiplier for security teams by automating threat investigation, alert triage, and response actions. By mimicking the workflow of a human SOC analyst, Cyber AI Analyst provides contextual insights that accelerate incident response and reduce the manual workload on security teams.

With 24/7 autonomous monitoring, Darktrace / OT ensures that threats are continuously detected and investigated in real time. Whether facing ransomware, insider threats, or sophisticated nation-state attacks, organizations can rely on AI-driven security to contain threats before they disrupt operations.

Trusted by customers: Darktrace / OT recognized in Gartner Peer Insights

Source: Gartner Peer Insights (Oct 28th)

Beyond our recognition in the Gartner Magic Quadrant, we feel Darktrace / OT is one of the highest-rated CPS security solutions on Gartner Peer Insights, reflecting strong customer trust and validation. With a 4.9/5 overall rating and the highest "Willingness to Recommend" score among CPS vendors, organizations across critical infrastructure and industrial sectors recognize the impact of our AI-driven security approach. Source: Gartner Peer Insights (Oct 28th)

This strong customer endorsement underscores why leading enterprises trust Darktrace / OT to secure their CPS environments today and in the future.

Redefining the future of CPS security

It's our view that Darktrace’s recognition as the only Visionary in the Gartner Magic Quadrant for CPS Protection Platforms validates its leadership in next-generation industrial security. As cyber threats targeting critical infrastructure continue to rise, organizations must adopt AI-driven security solutions that can adapt, respond, and mitigate risks in real time.

We believe this recognition reinforces our commitment to innovation and our mission to secure the world’s most essential systems. This recognition reinforces our commitment to innovation and our mission to secure the world’s most essential systems.

® Download the full Gartner Magic Quadrant for CPS Protection Platforms

® Request a demo to see Darktrace OT in action.

Gartner, Magic Quadrant for CPS Protection Platforms , Katell Thielemann, Wam Voster, Ruggero Contu 12 February 2025

Gartner does not endorse any vendor, product or service depicted in its research publications and does not advise technology users to select only those vendors with the highest ratings or other designation. Gartner research publications consist of the opinions of Gartner’s research organization and should not be construed as statements of fact. Gartner disclaims all warranties, expressed or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose.

GARTNER is a registered trademark and service mark of Gartner and Magic Quadrant and Peer Insights are a registered trademark, of Gartner, Inc. and/or its affiliates in the U.S. and internationally and are used herein with permission. All rights reserved. Gartner Peer Insights content consists of the opinions of individual end users based on their own experiences with the vendors listed on the platform, should not be construed as statements of fact, nor do they represent the views of Gartner or its affiliates. Gartner does not endorse any vendor, product or service depicted in this content nor makes any warranties, expressed or implied, with respect to this content, about its accuracy or completeness, including any warranties of merchantability or fitness for a particular purpose.

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Pallavi Singh
Product Marketing Manager, OT Security & Compliance

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March 28, 2025

Survey Findings: AI Cybersecurity Priorities and Objectives in 2025

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AI is changing the cybersecurity field, both on the offensive and defensive sides. We surveyed over 1,500 cybersecurity professionals from around the world to uncover their attitudes, understanding, and priorities when it comes to AI cybersecurity in 2025. Our full report, unearthing some telling trends, is available now.  

Download the full report to explore these findings in depth

It is clear that security professionals know their field is changing fast, and that AI will continue to influence those changes. Our survey results show that they are aware that the rise of AI will require them to adopt new tools and learn to use them effectively. Still, they aren’t always certain about how to plan for the future, or what to invest in.

The top priorities of security stakeholders for improving their defenses against AI-powered threats include augmenting their existing tool stacks with AI-powered solutions and improving integration among their security tools.

Figure 1: Year-over-year changes to the priorities of securitystakeholders.

Increasing cybersecurity staff

As was also the case last year, security stakeholders are less interested in hiring additional staff than in adding new AI-powered tools onto their existing security stacks, with only with 11% (and only 8% of executives) planning to increase cybersecurity staff in 2025.

This suggests that leaders are looking for new methods to overcome talent resource shortages.

Adding AI-powered security tools to supplement existing solutions

Executives are particularly enthusiastic about adopting AI-driven tools. Within that goal, there is consensus about the qualities cyber professionals are looking for when purchasing new security capabilities or replacing existing products.

  • 87% of survey respondents prefer solutions that are part of a broader platform over individual point products

These results are similar to last year’s, where again, almost nine out of ten agreed that a platform-oriented security solution was more effective at stopping cyber threats than a collection of individual products.

  • 88% of survey respondents agree that the use of AI within the security stack is critical to freeing up time for security teams to become more proactive, compared to reactive

AI itself can contribute to this shift from reactive to proactive security, improving risk prioritization and automating preventative strategies like Attack Surface Management (ASM) and proactive exposure management.

  • 84% of survey respondents prefer defensive AI solutions that do not require the organization’s data to be shared externally

This preference may reflect increasing attention to the data privacy and security risks posed by generative AI (gen AI) adoption. It may also reflect growing awareness of data residency requirements and other restrictions that regulators are imposing.

Improving cybersecurity awareness training for end users

Based on the survey results, practitioners in SecOps are more interested in improving security awareness training.

This goal is not necessarily mutually exclusive from the addition of AI tools. For example, teams can leverage AI to build more effective security awareness training programs, and as gen AI tools are adopted, users will need to be taught about data privacy and associated security risks.

Looking towards the future

One conclusion we can draw from the attitudinal shifts from last year’s survey to this year’s: while hiring more security staff might be a nice-to-have, implementing AI-powered tools so that existing employees can work smarter is increasingly viewed as a must-have.

However, trending goals are not just about managing resources, whether headcount or AI investments, to keep up with workloads. Existing end users must also be trained to follow safe practices while using established and newly adopted tools.

Security professionals, including executives, SecOps, and every role in between, continue to shift their identified challenges and priorities as they gear up for the coming year in the Era of AI.

State of AI report

Download the full report to explore these findings in depth

The full report for Darktrace’s State of AI Cybersecurity is out now. Download the paper to dig deeper into these trends, and see how results differ by industry, region, organization size, and job title.  

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