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February 17, 2021

Compromised 2FA: Preventing Microsoft Account Takeovers

Discover how Darktrace's Microsoft 365 connector detected and investigated a 2FA-compromised Microsoft account takeover. Learn these preventative measures!
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.
Written by
Max Heinemeyer
Global Field CISO
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17
Feb 2021

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.
Written by
Max Heinemeyer
Global Field CISO

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May 7, 2025

Anomaly-based threat hunting: Darktrace's approach in action

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What is threat hunting?

Threat hunting in cybersecurity involves proactively and iteratively searching through networks and datasets to detect threats that evade existing automated security solutions. It is an important component of a strong cybersecurity posture.

There are several frameworks that Darktrace analysts use to guide how threat hunting is carried out, some of which are:

  • MITRE Attack
  • Tactics, Techniques, Procedures (TTPs)
  • Diamond Model for Intrusion Analysis
  • Adversary, Infrastructure, Victims, Capabilities
  • Threat Hunt Model – Six Steps
  • Purpose, Scope, Equip, Plan, Execute, Feedback
  • Pyramid of Pain

These frameworks are important in baselining how to run a threat hunt. There are also a combination of different methods that allow defenders diversity– regardless of whether it is a proactive or reactive threat hunt. Some of these are:

  • Hypothesis-based threat hunting
  • Analytics-driven threat hunting
  • Automated/machine learning hunting
  • Indicator of Compromise (IoC) hunting
  • Victim-based threat hunting

Threat hunting with Darktrace

At its core, Darktrace is an anomaly-based detection tool. It combines various machine learning types that allows it to characterize what constitutes ‘normal’, based on the analysis of many different measures of a device or actor’s behavior. Those types of learning are then curated into what are called models.

Darktrace models leverage anomaly detection and integrate outputs from Darktrace Deep Packet Inspection, telemetry inputs, and additional modules, creating tailored activity detection.

This dynamic understanding allows Darktrace to identify, with a high degree of precision, events or behaviors that are both anomalous and unlikely to be benign.  On top of machine learning models for detection, there is also the ability to change and create models showcasing the tool’s diversity. The Model Editor allows security teams to specify values, priorities, thresholds, and actions they want to detect. That means a team can create custom detection models based on specific use cases or business requirements. Teams can also increase the priority of existing detections based on their own risk assessments to their environment.

This level of dexterity is particularly useful when conducting a threat hunt. As described above, and in previous ‘Inside the SOC’ blogs such a threat hunt can be on a specific threat actor, specific sector, or a  hypothesis-based threat hunt combined with ‘experimenting’ with some of Darktrace’s models.

Conducting a threat hunt in the energy sector with experimental models

In Darktrace’s recent Threat Research report “AI & Cybersecurity: The state of cyber in UK and US energy sectors” Darktrace’s Threat Research team crafted hypothesis-driven threat hunts, building experimental models and investigating existing models to test them and detect malicious activity across Darktrace customers in the energy sector.

For one of the hunts, which hypothesised utilization of PerfectData software and multi-factor authentication (MFA) bypass to compromise user accounts and destruct data, an experimental model was created to detect a Software-as-a-Service (SaaS) user performing activity relating to 'PerfectData Software’, known to allow a threat actor to exfiltrate whole mailboxes as a PST file. Experimental model alerts caused by this anomalous activity were analyzed, in conjunction with existing SaaS and email-related models that would indicate a multi-stage attack in line with the hypothesis.

Whilst hunting, Darktrace researchers found multiple model alerts for this experimental model associated with PerfectData software usage, within energy sector customers, including an oil and gas investment company, as well as other sectors. Upon further investigation, it was also found that in June 2024, a malicious actor had targeted a renewable energy infrastructure provider via a PerfectData Software attack and demonstrated intent to conduct an Operational Technology (OT) attack.

The actor  logged into Azure AD from a rare US IP address. They then granted Consent to ‘eM Client’ from the same IP. Shortly after, the actor granted ‘AddServicePrincipal’ via Azure  to PerfectData Software. Two days later, the actor created a  new email rule from a London IP to move emails to an RSS Feed Folder, stop processing rules, and mark emails as read. They then accessed mail items in the “\Sent” folder from a malicious IP belonging to anonymization network,  Private Internet Access Virtual Private Network (PIA VPN). The actor then conducted mass email deletions , deleting multiple instances of emails with subject “[Name] shared "[Company Name] Proposal" With You” from the  “\Sent folder”. The emails’ subject suggests the email likely contains a link to file storage for phishing purposes. The mass deletion likely represented an attempt to obfuscate a potential outbound phishing email campaign.

The Darktrace Model Alert that triggered for the mass deletes of the likely phishing email containing a file storage link.
Figure 1: The Darktrace Model Alert that triggered for the mass deletes of the likely phishing email containing a file storage link.

A month later, the same user was observed downloading mass mLog CSV files related to proprietary and Operational Technology information. In September, three months after the initial attack, another mass download of operational files occurred by this actor, pertaining to operating instructions and measurements, The observed patience and specific file downloads seemingly demonstrated an intent to conduct or research possible OT attack vectors. An attack on OT could have significant impacts including operational downtime, reputational damage, and harm to everyday operations. Darktrace alerted the impacted customer once findings were verified, and subsequent actions were taken by the internal security team to prevent further malicious activity.

Conclusion

Harnessing the power of different tools in a security stack is a key element to cyber defense. The above hypothesis-based threat hunt and custom demonstrated intent to conduct an experimental model creation demonstrates different threat hunting approaches, how Darktrace’s approach can be operationalized, and that proactive threat hunting can be a valuable complement to traditional security controls and is essential for organizations facing increasingly complex threat landscapes.

Credit to Nathaniel Jones (VP, Security & AI Strategy, Field CISO at Darktrace) and Zoe Tilsiter (EMEA Consultancy Lead)

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About the author
Nathaniel Jones
VP, Security & AI Strategy, Field CISO

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May 6, 2025

Combatting the Top Three Sources of Risk in the Cloud

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With cloud computing, organizations are storing data like intellectual property, trade secrets, Personally Identifiable Information (PII), proprietary code and statistics, and other sensitive information in the cloud. If this data were to be accessed by malicious actors, it could incur financial loss, reputational damage, legal liabilities, and business disruption.

Last year data breaches in solely public cloud deployments were the most expensive type of data breach, with an average of $5.17 million USD, a 13.1% increase from the year before.

So, as cloud usage continues to grow, the teams in charge of protecting these deployments must understand the associated cybersecurity risks.

What are cloud risks?

Cloud threats come in many forms, with one of the key types consisting of cloud risks. These arise from challenges in implementing and maintaining cloud infrastructure, which can expose the organization to potential damage, loss, and attacks.

There are three major types of cloud risks:

1. Misconfigurations

As organizations struggle with complex cloud environments, misconfiguration is one of the leading causes of cloud security incidents. These risks occur when cloud settings leave gaps between cloud security solutions and expose data and services to unauthorized access. If discovered by a threat actor, a misconfiguration can be exploited to allow infiltration, lateral movement, escalation, and damage.

With the scale and dynamism of cloud infrastructure and the complexity of hybrid and multi-cloud deployments, security teams face a major challenge in exerting the required visibility and control to identify misconfigurations before they are exploited.

Common causes of misconfiguration come from skill shortages, outdated practices, and manual workflows. For example, potential misconfigurations can occur around firewall zones, isolated file systems, and mount systems, which all require specialized skill to set up and diligent monitoring to maintain

2. Identity and Access Management (IAM) failures

IAM has only increased in importance with the rise of cloud computing and remote working. It allows security teams to control which users can and cannot access sensitive data, applications, and other resources.

Cybersecurity professionals ranked IAM skills as the second most important security skill to have, just behind general cloud and application security.

There are four parts to IAM: authentication, authorization, administration, and auditing and reporting. Within these, there are a lot of subcomponents as well, including but not limited to Single Sign-On (SSO), Two-Factor Authentication (2FA), Multi-Factor Authentication (MFA), and Role-Based Access Control (RBAC).

Security teams are faced with the challenge of allowing enough access for employees, contractors, vendors, and partners to complete their jobs while restricting enough to maintain security. They may struggle to track what users are doing across the cloud, apps, and on-premises servers.

When IAM is misconfigured, it increases the attack surface and can leave accounts with access to resources they do not need to perform their intended roles. This type of risk creates the possibility for threat actors or compromised accounts to gain access to sensitive company data and escalate privileges in cloud environments. It can also allow malicious insiders and users who accidentally violate data protection regulations to cause greater damage.

3. Cross-domain threats

The complexity of hybrid and cloud environments can be exploited by attacks that cross multiple domains, such as traditional network environments, identity systems, SaaS platforms, and cloud environments. These attacks are difficult to detect and mitigate, especially when a security posture is siloed or fragmented.  

Some attack types inherently involve multiple domains, like lateral movement and supply chain attacks, which target both on-premises and cloud networks.  

Challenges in securing against cross-domain threats often come from a lack of unified visibility. If a security team does not have unified visibility across the organization’s domains, gaps between various infrastructures and the teams that manage them can leave organizations vulnerable.

Adopting AI cybersecurity tools to reduce cloud risk

For security teams to defend against misconfigurations, IAM failures, and insecure APIs, they require a combination of enhanced visibility into cloud assets and architectures, better automation, and more advanced analytics. These capabilities can be achieved with AI-powered cybersecurity tools.

Such tools use AI and automation to help teams maintain a clear view of all their assets and activities and consistently enforce security policies.

Darktrace / CLOUD is a Cloud Detection and Response (CDR) solution that makes cloud security accessible to all security teams and SOCs by using AI to identify and correct misconfigurations and other cloud risks in public, hybrid, and multi-cloud environments.

It provides real-time, dynamic architectural modeling, which gives SecOps and DevOps teams a unified view of cloud infrastructures to enhance collaboration and reveal possible misconfigurations and other cloud risks. It continuously evaluates architecture changes and monitors real-time activity, providing audit-ready traceability and proactive risk management.

Real-time visibility into cloud assets and architectures built from network, configuration, and identity and access roles. In this unified view, Darktrace / CLOUD reveals possible misconfigurations and risk paths.
Figure 1: Real-time visibility into cloud assets and architectures built from network, configuration, and identity and access roles. In this unified view, Darktrace / CLOUD reveals possible misconfigurations and risk paths.

Darktrace / CLOUD also offers attack path modeling for the cloud. It can identify exposed assets and highlight internal attack paths to get a dynamic view of the riskiest paths across cloud environments, network environments, and between – enabling security teams to prioritize based on unique business risk and address gaps to prevent future attacks.  

Darktrace’s Self-Learning AI ensures continuous cloud resilience, helping teams move from reactive to proactive defense.

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About the author
Pallavi Singh
Product Marketing Manager, OT Security & Compliance
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