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February 17, 2021

Compromised 2FA: Preventing Microsoft Account Takeovers

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17
Feb 2021
Discover how Darktrace's Microsoft 365 connector detected and investigated a 2FA-compromised Microsoft account takeover. Learn these preventative measures!

What is Two-factor authentication (2FA)?

2FA is now relied upon by almost a third of businesses. It requires a user to present more than one method of identification when logging into an account. This prevents cyber-criminals from simply using password credentials to hack a system; instead, extra security layers, such as biometrics (inherence), personal information (knowledge), or a code sent to your phone or email (possession), are required to gain access to an account.

What happens when 2FA has been compromised?

Darktrace recently observed this exact scenario when a Microsoft 365 account was hijacked and the attacker temporarily changed the authentication settings so that the SMS codes were sent to their phone. The attack attempted to blend into the user activity and remain undetected. However, Darktrace was able to identify the account compromise from subtle anomalies in the user’s behavior, including suspicious logins, unusual email rule creations, and file deletions.

There has been a sharp increase in these SaaS-based attacks, which comes as no surprise as companies increasingly rely on SaaS platforms to conduct their remote business. Microsoft 365 is now used regularly across organizations for email, user management, file storage and sharing. This phenomenon has widened the attack surface and provides great opportunities for cyber-criminals. SaaS platforms are often siloed, and security teams tend to lack visibility over them and struggle to correlate events across these multiple platforms.

Darktrace Cyber AI protects the entire SaaS environment, providing full coverage over Microsoft 365 and Azure platforms. In this case, the customer was using the Microsoft 365 module. Despite the attack bypassing all other security tools, it was identified by Darktrace’s Microsoft 365 connector and investigated by Cyber AI Analyst – the world’s first AI investigation technology, which automatically triages, interprets, and reports on the full scope of security incidents.

How a Microsoft account was compromised through 2FA

An account belonging to a user on the financial team of a company with around 10,000 Microsoft 365 users was recently compromised. The initial infection most likely happened because the employee had clicked on a malicious link in a phishing email.

Figure 1: A timeline of the attack

Darktrace began detecting suspicious logins into the Microsoft 365 account from unusual locations in the US and Ghana. These logins successfully passed the multi-factor authentication (MFA) security, as the attacker had subtly manipulated the user’s details, modifying the registered phone number so the authentication text message went directly to them.

Figure 2: Darktrace’s dedicated SaaS console surfaces unusual activity across Microsoft 365

2FA can be compromised using several tactics. It may be hacked via a SIM swapping attack or through the use of a malicious OAuth application. An attacker could even resort to a phishing or social-engineering attack, and work in real time to use the one-time password at the same time as the victim enters it on the phishing page.

Following the unusual logins, Darktrace observed that the attacker had changed email rules for the compromised user’s account, as well as several shared inboxes, including one related to credit control.

During this time, the attacker was seen accessing multiple emails in the compromised user’s inbox. The attacker may have been scouring the inbox for sensitive data, or familiarizing themselves with the user’s normal activity and writing style, enabling them to craft believable phishing emails impersonating the account owner. The attacker also deleted multiple emails for that user in an attempt to cover their tracks.

While the rest of the organization’s security stack was blind to this threat, Darktrace’s Microsoft 365 connector detected the anomalous behavior and launched an automated investigation with Cyber AI Analyst. The security team then responded, before the attacker was able to fully exploit some of the critical shared mailboxes.

Had the hacker been able to continue, they would have been able to access intellectual property (IP) and sensitive financial data about the organization and its customers. This could have served as ammunition for future fraudulent payment requests, which have been known to cost organizations tens of thousands of dollars.

Cyber AI Analyst investigates 2FA threat

Trained on hundreds of expert cyber analysts, Cyber AI Analyst conducts autonomous investigations on the full range of threats – including SaaS account compromise. In this case, it stitched together the anomalous login and user behavior and generated a natural language summary of the incident, ready for review. A human analyst would have taken an average of three hours to do this. Yet Cyber AI Analyst did it in a matter of seconds, delivering a 92% time saving.

Figure 3: A demonstration of how Cyber AI Analyst reports on unusual logins and file access

Concluding thoughts

The dynamic workforce is more dispersed than ever, relying on SaaS applications and sprawling IT systems to host valuable data. In this digitally globalized world, cyber security must also be ubiquitous, providing full visibility across the digital environment.

This cyber-attack was targeted and sophisticated. The attack had used compromised credentials so no bruteforce activity was seen prior to the successful logins. Furthermore, the attacker passed the two-factor authentication, as well as covering their tracks through deleted emails and blending into legitimate user activity.

Darktrace AI, however, detected the subtle anomalies in the user’s behavior and thus identified that there was an unwanted presence in the environment. Darktrace is able to cover attacks in cloud and SaaS across the entire attack lifecycle – from an initial spear phishing email to full account takeover – even when other security methods, such as 2FA, have been compromised. In these attacks, early detection and response is key. There could have been significant financial and reputational repercussions had Darktrace not detected the attack.

Thanks to Darktrace analyst Brianna Leddy for her insights on the above threat find.

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

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

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Reimagining Your SOC: Overcoming Alert Fatigue with AI-Led Investigations  

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The efficiency of a Security Operations Center (SOC) hinges on its ability to detect, analyze and respond to threats effectively. With advancements in AI and automation, key early SOC team metrics such as Mean Time to Detect (MTTD) have seen significant improvements:

  • 96% of defenders believing AI-powered solutions significantly boost the speed and efficiency of prevention, detection, response, and recovery.
  • Organizations leveraging AI and automation can shorten their breach lifecycle by an average of 108 days compared to those without these technologies.

While tool advances have improved performance and effectiveness in the detection phase, this has not been as beneficial to the next step of the process where initial alerts are investigated further to determine their relevance and how they relate to other activities. This is often measured with the metric Mean Time to Analysis (MTTA), although some SOC teams operate a two-level process with teams for initial triage to filter out more obviously uninteresting alerts and for more detailed analysis of the remainder. SOC teams continue to grapple with alert fatigue, overwhelmed analysts, and inefficient triage processes, preventing them from achieving the operational efficiency necessary for a high-performing SOC.

Addressing this core inefficiency requires extending AI's capabilities beyond detection to streamline and optimize the following investigative workflows that underpin effective analysis.

Challenges with SOC alert investigation

Detecting cyber threats is only the beginning of a much broader challenge of SOC efficiency. The real bottleneck often lies in the investigation process.

Detection tools and techniques have evolved significantly with the use of machine learning methods, improving early threat detection. However, after a detection pops up, human analysts still typically step in to evaluate the alert, gather context, and determine whether it’s a true threat or a false alarm and why. If it is a threat, further investigation must be performed to understand the full scope of what may be a much larger problem. This phase, measured by the mean time to analysis, is critical for swift incident response.

Challenges with manual alert investigation:

  • Too many alerts
  • Alerts lack context
  • Cognitive load sits with analysts
  • Insufficient talent in the industry
  • Fierce competition for experienced analysts

For many organizations, investigation is where the struggle of efficiency intensifies. Analysts face overwhelming volumes of alerts, a lack of consolidated context, and the mental strain of juggling multiple systems. With a worldwide shortage of 4 million experienced level two and three SOC analysts, the cognitive burden placed on teams is immense, often leading to alert fatigue and missed threats.

Even with advanced systems in place not all potential detections are investigated. In many cases, only a quarter of initial alerts are triaged (or analyzed). However, the issue runs deeper. Triaging occurs after detection engineering and alert tuning, which often disable many alerts that could potentially reveal true threats but are not accurate enough to justify the time and effort of the security team. This means some potential threats slip through unnoticed.

Understanding alerts in the SOC: Stopping cyber incidents is hard

Let’s take a look at the cyber-attack lifecycle and the steps involved in detecting and stopping an attack:

First we need a trace of an attack…

The attack will produce some sort of digital trace. Novel attacks, insider threats, and attacker techniques such as living-off-the-land can make attacker activities extremely hard to distinguish.

A detection is created…

Then we have to detect the trace, for example some beaconing to a rare domain. Initial detection alerts being raised underpin the MTTD (mean time to detection). Reducing this initial unseen duration is where we have seen significant improvement with modern threat detection tools.

When it comes to threat detection, the possibilities are vast. Your initial lead could come from anything: an alert about unusual network activity, a potential known malware detection, or an odd email. Once that lead comes in, it’s up to your security team to investigate further and determine if this is this a legitimate threat or a false alarm and what the context is behind the alert.

Investigation begins…

It doesn’t just stop at a detection. Typically, humans also need to look at the alert, investigate, understand, analyze, and conclude whether this is a genuine threat that needs a response. We normally measure this as MTTA (mean time to analyze).

Conducting the investigation effectively requires a high degree of skill and efficiency, as every second counts in mitigating potential damage. Security teams must analyze the available data, correlate it across multiple sources, and piece together the timeline of events to understand the full scope of the incident. This process involves navigating through vast amounts of information, identifying patterns, and discerning relevant details. All while managing the pressure of minimizing downtime and preventing further escalation.

Containment begins…

Once we confirm something as a threat, and the human team determines a response is required and understand the scope, we need to contain the incident. That's normally the MTTC (mean time to containment) and can be further split into immediate and more permanent measures.

For more about how AI-led solutions can help in the containment stage read here: Autonomous Response: Streamlining Cybersecurity and Business Operations

The challenge is not only in 1) detecting threats quickly, but also 2) triaging and investigating them rapidly and with precision, and 3) prioritizing the most critical findings to avoid missed opportunities. Effective investigation demands a combination of advanced tools, robust workflows, and the expertise to interpret and act on the insights they generate. Without these, organizations risk delaying critical containment and response efforts, leaving them vulnerable to greater impacts.

While there are further steps (remediation, and of course complete recovery) here we will focus on investigation.

Developing an AI analyst: How Darktrace replicates human investigation

Darktrace has been working on understanding the investigative process of a skilled analyst since 2017. By conducting internal research between Darktrace expert SOC analysts and machine learning engineers, we developed a formalized understanding of investigative processes. This understanding formed the basis of a multi-layered AI system that systematically investigates data, taking advantage of the speed and breadth afforded by machine systems.

With this research we found that the investigative process often revolves around iterating three key steps: hypothesis creation, data collection, and results evaluation.

All these details are crucial for an analyst to determine the nature of a potential threat. Similarly, they are integral components of our Cyber AI Analyst which is an integral component across our product suite. In doing so, Darktrace has been able to replicate the human-driven approach to investigating alerts using machine learning speed and scale.

Here’s how it works:

  • When an initial or third-party alert is triggered, the Cyber AI Analyst initiates a forensic investigation by building multiple hypotheses and gathering relevant data to confirm or refute the nature of suspicious activity, iterating as necessary, and continuously refining the original hypothesis as new data emerges throughout the investigation.
  • Using a combination of machine learning including supervised and unsupervised methods, NLP and graph theory to assess activity, this investigation engine conducts a deep analysis with incidents raised to the human team only when the behavior is deemed sufficiently concerning.
  • After classification, the incident information is organized and processed to generate the analysis summary, including the most important descriptive details, and priority classification, ensuring that critical alerts are prioritized for further action by the human-analyst team.
  • If the alert is deemed unimportant, the complete analysis process is made available to the human team so that they can see what investigation was performed and why this conclusion was drawn.
Darktrace cyber ai analyst workflow, how it works

To illustrate this via example, if a laptop is beaconing to a rare domain, the Cyber AI Analyst would create hypotheses including whether this could be command and control traffic, data exfiltration, or something else. The AI analyst then collects data, analyzes it, makes decisions, iterates, and ultimately raises a new high-level incident alert describing and detailing its findings for human analysts to review and follow up.

Learn more about Darktrace's Cyber AI Analyst

  • Cost Savings Equivalent to adding 30 full-time Level 2 analysts without increasing headcount
  • Minimize Business Risk Takes on the busy work from human analysts and elevates a team’s overall decision making
  • Improve Security Outcomes Identifies subtle, sophisticated threats through holistic investigations

Unlocking an efficient SOC

To create a mature and proactive SOC, addressing the inefficiencies in the alert investigation process is essential. By extending AI's capabilities beyond detection, SOC teams can streamline and optimize investigative workflows, reducing alert fatigue and enhancing analyst efficiency.

This holistic approach not only improves Mean Time to Analysis (MTTA) but also ensures that SOCs are well-equipped to handle the evolving threat landscape. Embracing AI augmentation and automation in every phase of threat management will pave the way for a more resilient and proactive security posture, ultimately leading to a high-performing SOC that can effectively safeguard organizational assets.

Every relevant alert is investigated

The Cyber AI Analyst is not a generative AI system, or an XDR or SEIM aggregator that simply prompts you on what to do next. It uses a multi-layered combination of many different specialized AI methods to investigate every relevant alert from across your enterprise, native, 3rd party, and manual triggers, operating at machine speed and scale. This also positively affects detection engineering and alert tuning, because it does not suffer from fatigue when presented with low accuracy but potentially valuable alerts.

Retain and improve analyst skills

Transferring most analysis processes to AI systems can risk team skills if they don't maintain or build them and if the AI doesn't explain its process. This can reduce the ability to challenge or build on AI results and cause issues if the AI is unavailable. The Cyber AI Analyst, by revealing its investigation process, data gathering, and decisions, promotes and improves these skills. Its deep understanding of cyber incidents can be used for skill training and incident response practice by simulating incidents for security teams to handle.

Create time for cyber risk reduction

Human cybersecurity professionals excel in areas that require critical thinking, strategic planning, and nuanced decision-making. With alert fatigue minimized and investigations streamlined, your analysts can avoid the tedious data collection and analysis stages and instead focus on critical decision-making tasks such as implementing recovery actions and performing threat hunting.

Stay tuned for part 3/3

Part 3/3 in the Reimagine your SOC series explores the preventative security solutions market and effective risk management strategies.

Coming soon!

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About the author
Brittany Woodsmall
Product Marketing Manager, AI & Attack Surface

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January 29, 2025

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Inside the SOC

Bytesize Security: Insider Threats in Google Workspace

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What is an insider threat?

An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.

Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.

For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.

Attack overview: Insider threat

In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.

While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.

A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.

Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.

In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.

Conclusion

Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.

Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.

Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Appendices

Darktrace Model Detections

SaaS / Resource::Unusual Download Of Externally Shared Google Workspace File

References

[1]https://www.adobe.com/creativecloud/file-types/image/vector/indd-file.html

MITRE ATT&CK Mapping

Technqiue – Tactic – ID

Data from Cloud Storage Object – COLLECTION -T1530

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About the author
Vivek Rajan
Cyber Analyst
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