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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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February 19, 2025

Darktrace Releases Annual 2024 Threat Insights

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Introduction: Darktrace’s threat research

Defenders must understand the threat landscape in order to protect against it. They can do that with threat intelligence.

Darktrace approaches threat intelligence with a unique perspective. Unlike traditional security vendors that rely on established patterns from past incidents, it uses a strategy that is rooted in the belief that identifying behavioral anomalies is crucial for identifying both known and novel threats.

For Darktrace analysts and researchers, the incidents detected by the AI solution mark the beginning of a deeper investigation, aiming to connect mitigated threats to wider trends from across the threat landscape. Through hindsight analysis, the Darktrace Threat Research team has highlighted numerous threats, including zero-day, n-day, and other novel attacks, showcasing their evolving nature and Darktrace’s ability to identify them.

In 2024, the Threat Research team observed major trends around vulnerabilities in internet-facing systems, new and re-emerging ransomware strains, and sophisticated email attacks. Read on to discover some of our key insights into the current cybersecurity threat landscape.

Multiple campaigns target vulnerabilities in internet-facing systems

It is increasingly common for threat actors to identify and exploit newly discovered vulnerabilities in widely used services and applications, and in some cases, these vulnerability exploitations occur within hours of disclosure.

In 2024, the most significant campaigns observed involved the ongoing exploitation of zero-day and n-day vulnerabilities in edge and perimeter network technologies. In fact, in the first half of the year, 40% of all identified campaign activity came from the exploitation of internet-facing devices. Some of the most common exploitations involved Ivanti Connect Secure (CS) and Ivanti Policy Secure (PS) appliances, Palo Alto Network (PAN-OS) firewall devices, and Fortinet appliances.

Darktrace helps security teams identify suspicious behavior quickly, as demonstrated with the critical vulnerability in PAN-OS firewall devices. The vulnerability was publicly disclosed on April 11, 2024, yet with anomaly-based detection, Darktrace’s Threat Research team was able to identify a range of suspicious behavior related to exploitation of this vulnerability, including command-and-control (C2) connectivity, data exfiltration, and brute-forcing activity, as early as March 26.

That means that Darktrace and our Threat Research team detected this Common Vulnerabilities and Exposure (CVE) exploitation 16 days before the vulnerability was disclosed. Addressing critical vulnerabilities quickly massively benefits security, as teams can reduce their effectiveness by slowing malicious operations and forcing attackers to pursue more costly and time-consuming methods.

Persistent ransomware threats continue to evolve

The continued adoption of the Ransomware-as-a-Service (RaaS) model provides even less experienced threat actors with the tools needed to carry out disruptive attacks, significantly lowering the barrier to entry.

The Threat Research team tracked both novel and re-emerging strains of ransomware across the customer fleet, including Akira, LockBit, and Lynx. Within these ransomware attempts and incidents, there were notable trends in attackers’ techniques: using phishing emails as an attack vector, exploiting legitimate tools to mask C2 communication, and exfiltrating data to cloud storage services.

Read the Annual 2024 Threat Report for the complete list of prominent ransomware actors and their commonly used techniques.

Onslaught of email threats continues

With a majority of attacks originating from email, it is crucial that organizations secure the inboxes and beyond.

Between December 21, 2023, and December 18, 2024, Darktrace / EMAIL detected over 30.4 million phishing emails across the fleet. Of these, 70% successfully bypassed Domain-based Message Authentication, Reporting, and Conformance (DMARC) verification checks and 55% passed through all other existing layers of customer email security.

The abuse of legitimate services and senders continued to be a significant method for threat actors throughout 2024. By leveraging trusted platforms and domains, malicious actors can bypass traditional security measures and increase the likelihood of their phishing attempts being successful.

This past year, there was a substantial use of legitimately authenticated senders and previously established domains, with 96% of phishing emails detected by Darktrace / EMAIL utilizing existing domains rather than registering new ones.

These are not the only types of email attacks we observed. Darktrace detected over 2.7 million emails with multistage payloads.

While most traditional cybersecurity solutions struggle to cover multiple vectors and recognize each stage of complex attacks as part of wider malicious activity, Darktrace can detect and respond across email, identities, network, and cloud.

Conclusion

The Darktrace Threat Research team continues to monitor the ever-evolving threat landscape. Major patterns over the last year have revealed the importance of fast-acting, anomaly-based detection like Darktrace provides.

For example, response speed is essential when campaigns target vulnerabilities in internet-facing systems, and these vulnerabilities can be exploited by attackers within hours of their disclosure if not even before that.

Similarly, anomaly-based detection can identify hard to find threats like ransomware attacks that increasingly use living-off-the-land techniques and legitimate tools to hide malicious activity. A similar pattern can be found in the realm of email security, where attacks are also getting harder to spot, especially as they frequently exploit trusted senders, use redirects via legitimate services, and craft attacks that bypass DMARC and other layers of email security.

As attacks appear with greater complexity, speed, and camouflage, defenders must have timely detection and containment capabilities to handle all emerging threats. These hard-to-spot attacks can be identified and stopped by Darktrace.

Download the full report

Discover the latest threat landscape trends and recommendations from the Darktrace Threat Research team.

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The Darktrace Threat Research Team

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February 18, 2025

Unifying IT & OT With AI-Led Investigations for Industrial Security

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As industrial environments modernize, IT and OT networks are converging to improve efficiency, but this connectivity also creates new attack paths. Previously isolated OT systems are now linked to IT and cloud assets, making them more accessible to attackers.

While organizations have traditionally relied on air gaps, firewalls, data diodes, and access controls to separate IT and OT, these measures alone aren’t enough. Threat actors often infiltrate IT/Enterprise networks first then exploit segmentation, compromising credentials, or shared IT/OT systems to move laterally, escalate privileges, and ultimately enter the OT network.

To defend against these threats, organizations must first ensure they have complete visibility across IT and OT environments.

Visibility: The first piece of the puzzle

Visibility is the foundation of effective industrial cybersecurity, but it’s only the first step. Without visibility across both IT and OT, security teams risk missing key alerts that indicate a threat targeting OT at their earliest stages.

For Attacks targeting OT, early stage exploits often originate in IT environments, adversaries perform internal reconnaissance among other tactics and procedures but then laterally move into OT first affecting IT devices, servers and workstations within the OT network. If visibility is limited, these threats go undetected. To stay ahead of attackers, organizations need full-spectrum visibility that connects IT and OT security, ensuring no early warning signs are missed.

However, visibility alone isn’t enough. More visibility also means more alerts, this doesn’t just make it harder to separate real threats from routine activity, but bogs down analysts who have to investigate all these alerts to determine their criticality.

Investigations: The real bottleneck

While visibility is essential, it also introduces a new challenge: Alert fatigue. Without the right tools, analysts are often occupied investigating alerts with little to no context, forcing them to manually piece together information and determine if an attack is unfolding. This slows response times and increases the risk of missing critical threats.

Figure 1: Example ICS attack scenario

With siloed visibility across IT and OT each of these events shown above would be individually alerted by a detection engine with little to no context nor correlation. Thus, an analyst would have to try to piece together these events manually. Traditional security tools struggle to keep pace with the sophistication of these threats, resulting in an alarming statistic: less than 10% of alerts are thoroughly vetted, leaving organizations vulnerable to undetected breaches. As a result, incidents inevitably follow.

Darktrace’s Cyber AI Analyst uses AI-led investigations to improve workflows for analysts by automatically correlating alerts wherever they occur across both IT and OT. The multi-layered AI engine identifies high-priority incidents, and provides analysts with clear, actionable insights, reducing noise and highlighting meaningful threats. The AI significantly alleviates workloads, enabling teams to respond faster and more effectively before an attack escalates.

Overcoming organizational challenges across IT and OT

Beyond technical challenges like visibility and alert management, organizational dynamics further complicate IT-OT security efforts. Fundamental differences in priorities, workflows, and risk perspectives create challenges that can lead to misalignment between teams:

Non-transferable practices: IT professionals might assume that cybersecurity practices from IT environments can be directly applied to OT environments. This can lead to issues, as OT systems and workflows may not handle IT security processes as expected. It's crucial to recognize and respect the unique requirements and constraints of OT environments.

Segmented responsibilities: IT and OT teams often operate under separate organizational structures, each with distinct priorities, goals, and workflows. While IT focuses on data security, network integrity, and enterprise applications, OT prioritizes uptime, reliability, and physical processes.

Different risk perspectives: While IT teams focus on preventing cyber threats and regulatory violations, OT teams prioritize uptime and operational reliability making them drawn towards asset inventory tools that provide no threat detection capability.

Result: A combination of disparate and ineffective tools and misaligned teams can make any progress toward risk reduction at an organization seem impossible. The right tools should be able to both free up time for collaboration and prompt better communication between IT and OT teams where it is needed. However, different size operations structure their IT and OT teams differently which impacts the priorities for each team.

In real-world scenarios, small IT teams struggle to manage security across both IT and OT, while larger organizations with OT security teams face alert fatigue and numerous false positives slowing down investigations and hindering effective communication with the IT security teams.

By unifying visibility and investigations, Darktrace / OT helps organizations of all sizes detect threats earlier, streamline workflows, and enhance security across both IT and OT environments. The following examples illustrate how AI-driven investigations can transform security operations, improving detection, investigation, and response.

Before and after AI-led investigation

Before: Small manufacturing company

At a small manufacturing company, a 1-3 person IT team juggles everything from email security to network troubleshooting. An analyst might see unusual traffic through the firewall:

  • Unusual repeated outbound traffic from an IP within their OT network destined to an unidentifiable external IP.

With no dedicated OT security tools and limited visibility into the industrial network, they don’t know what the internal device in question is, if it is beaconing to a malicious external IP, and what it may be doing to other devices within the OT network. Without a centralized dashboard, they must manually check logs, ask operators about changes, and hunt for anomalies across different systems.

After a day of investigation, they concluded the traffic was not to be expected activity. They stop production within their smaller OT network, update their firewall rules and factory reset all OT devices and systems within the blast radius of the IP device in question.

After: Faster, automated response with Cyber AI Analyst

With Darktrace / OT and Cyber AI Analyst, the IT team moves from reactive, manual investigations to proactive, automated threat detection:

  • Cyber AI Analyst connects alerts across their IT and OT infrastructure temporally mapping them to attack frameworks and provides contextual analysis of how alerts are linked, revealing in real time attackers attempting lateral movement from IT to OT.
  • A human-readable incident report explains the full scope of the incident, eliminating hours of manual investigation.
  • The team is faster to triage as they are led directly to prioritized high criticality alerts, now capable of responding immediately instead of wasting valuable time hunting for answers.

By reducing noise, providing context, and automating investigations, Cyber AI Analyst transforms OT security, enabling small IT teams to detect, understand, and respond to threats—without deep OT cybersecurity expertise.

Before: Large critical infrastructure organization

In large critical infrastructure operations, OT and IT teams work in separate silos. The OT security team needs to quickly assess and prioritize alerts, but their system floods them with notifications:

  • Multiple new device connected to the ICS network alerts
  • Multiple failed logins to HMI detected
  • Multiple Unusual Modbus/TCP commands detected
  • Repeated outbound OT traffic to IT destinations

At first glance, these alerts seem important, but without context, it’s unclear whether they indicate a routine error, a misconfiguration, or an active cyber-attack. They might ask:

  • Are the failed logins just a mistake, or a brute-force attempt?
  • Is the outbound traffic part of a scheduled update, or data exfiltration?

Without correlation across events, the engineer must manually investigate each one—checking logs, cross-referencing network activity, and contacting operators—wasting valuable time. Meanwhile, if it’s a coordinated attack, the adversary may already be disrupting operations.

After: A new workflow with Cyber AI Analyst

With Cyber AI Analyst, the OT security team gets clear, automated correlation of security events, making investigations faster and more efficient:

  • Automated correlation of OT threats: Instead of isolated alerts, Cyber AI Analyst stitches together related events, providing a single, high-confidence incident report that highlights key details.
  • Faster time to meaning: The system connects anomalous behaviors (e.g., failed logins, unusual traffic from an HMI, and unauthorized PLC modifications) into a cohesive narrative, eliminating hours of manual log analysis.
  • Prioritized and actionable alerts: OT security receives clear, ranked incidents, immediately highlighting what matters most.
  • Rapid threat understanding: Security teams know within minutes whether an event is a misconfiguration or a cyber-attack, allowing for faster containment.

With Cyber AI Analyst, large organizations cut through alert noise, accelerate investigations, and detect threats faster—without disrupting OT operations.

An AI-led approach to industrial cybersecurity

Security vendors with a primary focus on IT may lack insight into OT threats. Even OT-focused vendors have limited visibility into IT device exploitation within OT networks, leading to failed ability to detect early indicators of compromise. A comprehensive solution must account for the unique characteristics of various OT environments.

In a world where industrial security is no longer just about protecting OT but securing the entire digital-physical ecosystem as it interacts with the OT network, Darktrace / OT is an AI-driven solution that unifies visibility across IT, IoT and OT, Cloud into one cohesive defense strategy.

Whether an attack originates from an external breach, an insider threat, a supply chain compromise, in the Cloud, OT, or IT domains Cyber AI Analyst ensures that security teams see the full picture - before disruption occurs.

Learn more about Darktrace / OT 

  • Unify IT and OT security under a single platform, ensuring seamless communication and protection for all interconnected devices.
  • Maintain uptime with AI-driven threat containment, stopping attacks without disrupting production.
  • Mitigate risks with or without patches, leveraging MITRE mitigations to reduce attack opportunities.

Download the solution brief to see how Darktrace secures critical infrastructure.

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About the author
Daniel Simonds
Director of Operational Technology
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