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June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

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07
Jun 2020
We cover two real cases on how Darktrace stopped Microsoft 365 account takeovers by correlating insights across SaaS applications & email activity.

Social engineering’. ‘Credential theft’. ‘Account takeover’. If you were a fly on the wall of a Security Operations Center in 2020, you would have heard these phrases far more often than ‘banking trojan’, ‘SQL injection’ or ‘exploit kit’. The reason for this is simple – the reality for most security teams now is that their perimeter has shifted into the cloud. Identities are being attacked more than devices.

Microsoft 365 account compromise’ is the current favorite, with 29% of organizations reporting a related incident in one month alone. Security teams struggle with these attacks because the evidence needed to detect them is scattered across the enterprise: they begin via email, are executed over the network, and progress in the cloud. This broad and spread out digital footprint means that following the breadcrumbs is not easy.

Darktrace’s Cyber AI Platform is designed to understand a user’s behavior as they move between devices and cloud services, tracking their activity to identify a compromise. To help understand how these attacks avoid detection, it is useful to look at a couple of examples of Microsoft Office 365 compromise detected recently in one of our customers.

Microsoft 365 compromised to launch external email threat

A Microsoft 365 account was recently compromised at a public accounting firm based in the United States. Darktrace initially picked up on several anomalies, including a sudden surge in outbound email traffic as well as the unusual login location – while the company and nearly all of its users were located in Wisconsin, an IP address located in Kansas was used to log in to the Microsoft 365 account. Along with the unusual login, a login to Microsoft Teams from the same Kansas IP address was detected.

Figure 1: Just after the new email rule was created, a Microsoft Teams 100% rare IP login occurred.

‘Impossible travel’ rules alone would have missed these anomalies, but an understanding of activity and behavior across different SaaS applications allowed Darktrace’s AI to recognize these events as one systematic case of credential theft. When the threat-actor subsequently created a new email rule, Darktrace was able to connect this event with the other anomalous behavior and understand its potentially malicious nature.

Figure 2: Darktrace’s SaaS Module noted a 100% rare IP logging into the user’s Microsoft 365 account and the creation of a new mailbox rules. All factors indicated 100% unusual SaaS activity.

Five minutes later, Antigena Email alerted on a large number of outbound emails containing a generic subject line and an attached PDF. The technology also detected that there was a clear spike in outbound emails from this user and flagged each of these emails with the “Out of Character” tag, which in this case denoted a change from normal behavior with the surge in recipients, and likely internal compromise.

Figure 3: Antigena Email detected a surge in recipients that indicated a serious breach of normal behavior for this user.

The unusual login behavior detected by Darktrace’s SaaS Module could be connected to the anomalous outbound email behavior flagged by Antigena Email, allowing the security team to see the extent of the attack and neutralize it as it emerged. It was clear that the account was being used to engage in malicious activity, as each of the 220 outbound emails used a generic subject line and contained a suspicious attachment. The security team therefore immediately disabled the compromised account.

Figure 4: A recreation of the email sent by the attacker, containing the malicious attachment.

‘Change of bank details’ sent from accounts department

When an Accounts Department’s Microsoft 365 account was compromised and used to send targeted phishing emails, Darktrace was able to track the attacker’s movement within the inbox, tying together information from Darktrace’s SaaS Module with Antigena Email’s alerts to understand the full picture of the threat and stop the attack.

The SaaS account appears to have been compromised via an inbound spear phishing attack, or some other form of attack that occurred before Darktrace began monitoring the organization. While Darktrace Cyber AI had no oversight of the initial compromise, it was still able to distinguish later attacker behavior as malicious, based on its actively evolving understanding of the organization and its workforce.

When the account user logged in from a 100% rare French IP address, Darktrace’s SaaS Module picked up on the anomaly immediately, and further detected a series of activities carried out after the unusual login. At the same time, Antigena Email noted an email being sent.

Figure 5: The login from a French IP was noted as 100% rare for this user and SaaS account.

Darktrace then identified more activity occurring from a second rare login location, a Swiss IP address. Very little email activity occurred when the account was logged in from this IP. Instead, Cyber AI saw the threat-actor using their illegitimate SaaS access to view information on the legitimate account user and files related to banking, invoices, and payments.

Antigena Email then identified a series of email communications that, when seen in the context of the SaaS account compromise, pointed to a clear threat. There were no obvious malicious attachments or links in the emails. However, the subject of the final reply was ‘Change of Bank Details’, and the email prompted a high Solicitation Inducement Score within Antigena Email, strongly implying that the malicious actor had sent emails instructing the destination to change payment details in order to route money to the attacker, instead of the company.

It seems the attackers went through the banking and invoicing files in order to find a customer with a big bill to pay, then used the compromised email account to launch an outbound phishing attack, changing the billing details. With Darktrace AI correlating information within the SaaS platform and insights from Antigena Email, this targeted phishing attack could be contained before further compromise or damage could occur.

The below screenshot also indicates a series of inbox processing rules made on the compromised account, showing actions that are typical of an account takeover.

Figure 6: Darktrace’s records of new inbox rules being set up on the compromised SaaS account.

The benefits of a unified approach

These stories are all too familiar. Most security tools would not be able to take action on any one of these steps individually. But the combination reveals the tell-tale sign of a Microsoft 365 account hijack. Organizations are struggling to manage their user identities across their cloud infrastructure, and rule and policy-based detection is no longer feasible.

However, by learning identities and behavior across the enterprise, Darktrace is able to detect, and seamlessly respond, to combat these threats. Hundreds of organizations are now using Antigena Email to protect their email and cloud environments continuously, trusting it to dynamically enforce MFA, lock accounts, block network traffic, and withhold emails when necessary.

As cloud-native applications become more popular, organizations face the growing problem of separate end-to-end security solutions for each type of workload. With Antigena Email working in conjunction with Darktrace’s Enterprise Immune System, defenders can be assured that a single, unified platform is tracking every suspicious behavior, wherever it arises in the organization.

Learn more about Antigena Email

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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September 26, 2024

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Inside the SOC

Thread Hijacking: How Attackers Exploit Trusted Conversations to Infiltrate Networks

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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

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About the author
Maria Geronikolou
Cyber Analyst

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September 26, 2024

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How AI can help CISOs navigate the global cyber talent shortage

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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
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