Blog
/

Email

Threat Finds

/
August 26, 2020

Darktrace Detects Malicious ISO Files with AI Darktrace Email

Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
26
Aug 2020
Darktrace AI detects malicious ISO file in email attack. Learn more about how Antigena Email stopped the attack without relying on signatures or blacklists.

Darktrace has recently seen a string of email attacks that use some degree of social engineering to convince the recipient to open a misleading link and divulge their credentials. In this blog, we look at an email attack targeting a Spanish customer that involved hiding malicious content in an unusual file type that is not regularly checked by common email security tools.

An ISO file, often referred to as an ISO image, is an archive file that contains an identical copy of data found on an optical disc, like a CD or DVD. They are primarily used for backing up optical discs or distributing large file sets that are intended to be burned onto an optical disc. Since they are relatively unusual – and are typically extremely large files – most standard email controls don’t analyze them in any depth, if at all.

Darktrace detected one cyber-criminal using ISO files to inflict damage on a food distributor in Spain. The organization, which had adopted Antigena Email just two weeks earlier, received around 84 emails from the same sender, each containing a malicious ISO attachment. The emails were received from info@valeplaz[.]com, a clever and well-executed spoof of the email address info@valenplas[.]com, which is the contact email of a legitimate Spanish manufacturer – possibly even a supplier of the victim organization.

Figure 1: A snapshot of Antigena Email’s user interface

Darktrace noticed that the sender had never been seen in any prior correspondences across the business. Additionally, the personal field does not correspond with the header in the email itself – which is what would be visible to the recipient. In the connection IP address and checks, Darktrace’s AI revealed that the true sender does not correspond with the domain valeplaz[.]com.

The subject line suggests that the email is about an order the client made. Analyzing the attachments, Darktrace surfaced a file titled URGENTE_PO_120620.iso. The name of the file suggests the sender is attempting to use the social engineering tactic of urgency in order to alarm the recipients, leading them to jump into action and click a link or open attachments without carefully considering the details of the email.

Darktrace’s AI also recognized that the file extension .iso is highly anomalous for the group, user, and the organization as a whole. Even more suspiciously, the size of the attachment is incredibly small (just 485.4 kB), which makes it highly unlikely that it was, in fact, a genuine invoice in the form of a PDF or Word attachment. These findings, in conjunction with the New Contact and Wide Distribution tags of the email, caused Antigena Email to strip the email of the attachment and hold it back from each recipient’s inbox. In addition, Darktrace’s AI revealed that the email contained an anomalous link which it deemed highly suspicious, and locked the link in all emails while the security team investigated the incident.

Figure 2: The suspicious link in question

Stopping the attack without a Patient Zero

When the security team later checked the file hash on the attachment, they discovered that some anti-virus vendors, including Microsoft, had already labelled it as malware. The crucial challenge is to stop the malicious email in the first instance – before it lands in the first inbox. With a continuously updated understanding of ‘self’, Darktrace’s AI is able to do just that – stopping attacks without requiring a ‘Patient Zero’ be infected.

Moreover, many legacy solutions hadn’t yet recognized this file hash as malicious, suggesting that this was a relatively new attack. This exposes an increasingly obvious limitation of such tools – attackers are refreshing their attack infrastructure so often that no matter how frequently legacy tools or blacklists are updated, they are outdated almost immediately.

Antigena Email caught this attack without relying on any signatures and blacklists, but instead by learning whether or not the email, file, and behavior was normal for the unique business. With Cyber AI protecting their inbox, this organization was able to thwart this attack in the first instance – before any emails landed in an inbox or any employees clicked on the link.

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Author
Mariana Pereira
VP, Cyber Innovation

Mariana is the VP of Cyber Innovation at Darktrace, and works closely with the development, analyst, and marketing teams to advise technical and non-technical audiences on how best to augment cyber resilience, and how to implement AI technology as a means of defense. She speaks regularly at international events, with a specialism in presenting on sophisticated, AI-powered email attacks. She holds an MBA from the University of Chicago, and speaks several languages including French, Italian, and Portuguese.

Book a 1-1 meeting with one of our experts
Share this article

More in this series

No items found.

Blog

/

September 26, 2024

/

Inside the SOC

Thread Hijacking: How Attackers Exploit Trusted Conversations to Infiltrate Networks

Default blog imageDefault blog image

What is Thread Hijacking?

Cyberattacks are becoming increasingly stealthy and targeted, with malicious actors focusing on high-value individuals to gain privileged access to their organizations’ digital environments. One technique that has gained prominence in recent years is thread hijacking. This method allows attackers to infiltrate ongoing conversations, exploiting the trust within these threads to access sensitive systems.

Thread hijacking typically involves attackers gaining access to a user’s email account, monitoring ongoing conversations, and then inserting themselves into these threads. By replying to existing emails, they can send malicious links, request sensitive information, or manipulate the conversation to achieve their goals, such as redirecting payments or stealing credentials. Because such emails appear to come from a trusted source, they often bypass human security teams and traditional security filters.

How does threat hijacking work?

  1. Initial Compromise: Attackers first gain access to a user’s email account, often through phishing, malware, or exploiting weak passwords.
  2. Monitoring: Once inside, they monitor the user’s email threads, looking for ongoing conversations that can be exploited.
  3. Infiltration: The attacker then inserts themselves into these conversations, often replying to existing emails. Because the email appears to come from a trusted source within an ongoing thread, it bypasses many traditional security filters and raises less suspicion.
  4. Exploitation: Using the trust established in the conversation, attackers can send malicious links, request sensitive information, or manipulate the conversation to achieve their goals, such as redirecting payments or stealing credentials.

A recent incident involving a Darktrace customer saw a malicious actor attempt to manipulate trusted email communications, potentially exposing critical data. The attacker created a new mailbox rule to forward specific emails to an archive folder, making it harder for the customer to notice the malicious activity. This highlights the need for advanced detection and robust preventive tools.

Darktrace’s Self-Learning AI is able to recognize subtle deviations in normal behavior, whether in a device or a Software-as-a-Service (SaaS) user. This capability enables it to detect emerging attacks in their early stages. In this post, we’ll delve into the attacker’s tactics and illustrate how Darktrace / IDENTITY™ successfully identified and mitigated a thread hijacking attempt, preventing escalation and potential disruption to the customer’s network.

Threat hijacking attack overview & Darktrace coverage

On August 8, 2024, Darktrace detected an unusual email received by a SaaS account on a customer’s network. The email appeared to be a reply to a previous chain discussing tax and payment details, likely related to a transaction between the customer and one of their business partners.

Headers of the suspicious email received.
Figure 1: Headers of the suspicious email received.

A few hours later, Darktrace detected the same SaaS account creating a new mailbox rule named “.”, a tactic commonly used by malicious actors to evade detection when setting up new email rules [2]. This rule was designed to forward all emails containing a specific word to the user’s “Archives” folder. This evasion technique is typically used to move any malicious emails or responses to a rarely opened folder, ensuring that the genuine account holder does not see replies to phishing emails or other malicious messages sent by attackers [3].

Darktrace recognized the newly created email rule as suspicious after identifying the following parameters:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: “.”
  • FromAddressContainsWords: [Redacted]
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace also noted that the user attempting to create this new email rule had logged into the SaaS environment from an unusual IP address. Although the IP was located in the same country as the customer and the ASN used by the malicious actor was typical for the customer’s network, the rare IP, coupled with the anomalous behavior, raised suspicions.

Figure 2: Hijacked SaaS account creating the new mailbox rule.

Given the suspicious nature of this activity, Darktrace’s Security Operations Centre (SOC) investigated the incident and alerted the customer’s security team of this incident.

Due to a public holiday in the customer's location (likely an intentional choice by the threat actor), their security team did not immediately notice or respond to the notification. Fortunately, the customer had Darktrace's Autonomous Response capability enabled, which allowed it to take action against the suspicious SaaS activity without human intervention.

In this instance, Darktrace swiftly disabled the seemingly compromised SaaS user for 24 hours. This action halted the spread of the compromise to other accounts on the customer’s SaaS platform and prevented any sensitive data exfiltration. Additionally, it provided the security team with ample time to investigate the threat and remove the user from their environment. The customer also received detailed incident reports and support through Darktrace’s Security Operations Support service, enabling direct communication with Darktrace’s expert Analyst team.

Conclusion

Ultimately, Darktrace’s anomaly-based detection allowed it to identify the subtle deviations from the user’s expected behavior, indicating a potential compromise on the customer’s SaaS platform. In this case, Darktrace detected a login to a SaaS platform from an unusual IP address, despite the attacker’s efforts to conceal their activity by using a known ASN and logging in from the expected country.

Despite the attempted SaaS hijack occurring on a public holiday when the customer’s security team was likely off-duty, Darktrace autonomously detected the suspicious login and the creation of a new email rule. It swiftly blocked the compromised SaaS account, preventing further malicious activity and safeguarding the organization from data exfiltration or escalation of the compromise.

This highlights the growing need for AI-driven security capable of responding to malicious activity in the absence of human security teams and detect subtle behavioral changes that traditional security tools.

Credit to: Ryan Traill, Threat Content Lead for his contribution to this blog

Appendices

Darktrace Model Detections

SaaS / Compliance / Anomalous New Email Rule

Experimental / Antigena Enhanced Monitoring from SaaS Client Block

Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Antigena / SaaS / Antigena Email Rule Block

References

[1] https://blog.knowbe4.com/whats-the-best-name-threadjacking-or-man-in-the-inbox-attacks

[2] https://darktrace.com/blog/detecting-attacks-across-email-saas-and-network-environments-with-darktraces-combined-ai-approach

[3] https://learn.microsoft.com/en-us/defender-xdr/alert-grading-playbook-inbox-manipulation-rules

Continue reading
About the author
Maria Geronikolou
Cyber Analyst

Blog

/

September 26, 2024

/
No items found.

How AI can help CISOs navigate the global cyber talent shortage

Default blog imageDefault blog image

The global picture

4 million cybersecurity professionals are needed worldwide to protect and defend the digital world – twice the number currently in the workforce.1

Innovative technologies are transforming business operations, enabling access to new markets, personalized customer experiences, and increased efficiency. However, this digital transformation also challenges Security Operations Centers (SOCs) with managing and protecting a complex digital environment without additional resources or advanced skills.

At the same time, the cybersecurity industry is suffering a severe global skills shortage, leaving many SOCs understaffed and under-skilled. With a 72% increase in data breaches from 2021-20232, SOCs are dealing with overwhelming alert volumes from diverse security tools. Nearly 60% of cybersecurity professionals report burnout3, leading to high turnover rates. Consequently, only a fraction of alerts are thoroughly investigated, increasing the risk of undetected breaches. More than half of organizations that experienced breaches in 2024 admitted to having short-staffed SOCs.4

How AI can help organizations do more with less

Cyber defense needs to evolve at the same pace as cyber-attacks, but the global skills shortage is making that difficult. As threat actors increasingly abuse AI for malicious purposes, using defensive AI to enable innovation and optimization at scale is reshaping how organizations approach cybersecurity.

The value of AI isn’t in replacing humans, but in augmenting their efforts and enabling them to scale their defense capabilities and their value to the organization. With AI, cybersecurity professionals can operate at digital speed, analyzing vast data sets, identifying more vulnerabilities with higher accuracy, responding and triaging faster, reducing risks, and implementing proactive measures—all without additional staff.

Research indicates that organizations leveraging AI and automation extensively in security functions—such as prevention, detection, investigation, or response—reduced their average mean time to identify (MTTI) and mean time to contain (MTTC) data breaches by 33% and 43%, respectively. These organizations also managed to contain breaches nearly 100 days faster on average compared to those not using AI and automation.5

First, you've got to apply the right AI to the right security challenge. We dig into how different AI technologies can bridge specific skills gaps in the CISO’s Guide to Navigating the Cybersecurity Skills Shortage.

Cases in point: AI as a human force multiplier

Let’s take a look at just some of the cybersecurity challenges to which AI can be applied to scale defense efforts and relieve the burden on the SOC. We go further into real-life examples in our white paper.

Automated threat detection and response

AI enables 24/7 autonomous response, eliminating the need for after-hours SOC shifts and providing security leaders with peace of mind. AI can scale response efforts by analyzing vast amounts of data in real time, identifying anomalies, and initiating precise autonomous actions to contain incidents, which buys teams time for investigation and remediation.  

Triage and investigation

AI enhances the triage process by automatically categorizing and prioritizing security alerts, allowing cybersecurity professionals to focus on the most critical threats. It creates a comprehensive picture of an attack, helps identify its root cause, and generates detailed reports with key findings and recommended actions.  

Automation also significantly reduces overwhelming alert volumes and high false positive rates, enabling analysts to concentrate on high-priority threats and engage in more proactive and strategic initiatives.

Eliminating silos and improving visibility across the enterprise

Security and IT teams are overwhelmed by the technological complexity of operating multiple tools, resulting in manual work and excessive alerts. AI can correlate threats across the entire organization, enhancing visibility and eliminating silos, thereby saving resources and reducing complexity.

With 88% of organizations favoring a platform approach over standalone solutions, many are consolidating their tech stacks in this direction. This consolidation provides native visibility across clouds, devices, communications, locations, applications, people, and third-party security tools and intelligence.

Upskilling your existing talent in AI

As revealed in the State of AI Cybersecurity Survey 2024, only 26% of cybersecurity professionals say they have a full understanding of the different types of AI in use within security products.6

Understanding AI can upskill your existing staff, enhancing their expertise and optimizing business outcomes. Human expertise is crucial for the effective and ethical integration of AI. To enable true AI-human collaboration, cybersecurity professionals need specific training on using, understanding, and managing AI systems. To make this easier, the Darktrace ActiveAI Security Platform is designed to enable collaboration and reduce the learning curve – lowering the barrier to entry for junior or less skilled analysts.  

However, to bridge the immediate expertise gap in managing AI tools, organizations can consider expert managed services that take the day-to-day management out of the SOC’s hands, allowing them to focus on training and proactive initiatives.

Conclusion

Experts predict the cybersecurity skills gap will continue to grow, increasing operational and financial risks for organizations. AI for cybersecurity is crucial for CISOs to augment their teams and scale defense capabilities with speed, scalability, and predictive insights, while human expertise remains vital for providing the intuition and problem-solving needed for responsible and efficient AI integration.

If you’re thinking about implementing AI to solve your own cyber skills gap, consider the following:

  • Select an AI cybersecurity solution tailored to your specific business needs
  • Review and streamline existing workflows and tools – consider a platform-based approach to eliminate inefficiencies
  • Make use of managed services to outsource AI expertise
  • Upskill and reskill existing talent through training and education
  • Foster a knowledge-sharing culture with access to knowledge bases and collaboration tools

Interested in how AI could augment your SOC to increase efficiency and save resources? Read our longer CISO’s Guide to Navigating the Cybersecurity Skills Shortage.

And to better understand cybersecurity practitioners' attitudes towards AI, check out Darktrace’s State of AI Cybersecurity 2024 report.

References

  1. https://www.isc2.org/research  
  2. https://www.forbes.com/advisor/education/it-and-tech/cybersecurity-statistics/  
  3. https://www.informationweek.com/cyber-resilience/the-psychology-of-cybersecurity-burnout  
  4. https://www.ibm.com/downloads/cas/1KZ3XE9D  
  5. https://www.ibm.com/downloads/cas/1KZ3XE9D  
  6. https://darktrace.com/resources/state-of-ai-cyber-security-2024
Continue reading
About the author
The Darktrace Community
Your data. Our AI.
Elevate your network security with Darktrace AI