Blog
/
/
June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

We cover two real cases on how Darktrace stopped Microsoft 365 account takeovers by correlating insights across SaaS applications & email activity.
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
Dan Fein
VP, Product
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
07
Jun 2020

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.
Written by
Dan Fein
VP, Product

More in this series

No items found.

Blog

/

Network

/

April 2, 2026

How Chinese-Nexus Cyber Operations Have Evolved – And What It Means For Cyber Risk and Resilience 

Chinese-Nexus Cyber OperationsDefault blog imageDefault blog image

Cybersecurity has traditionally organized risk around incidents, breaches, campaigns, and threat groups. Those elements still matter—but if we fixate on individual incidents, we risk missing the shaping of the entire ecosystem. Nation‑state–aligned operators are increasingly using cyber operations to establish long-term strategic leverage, not just to execute isolated attacks or short‑term objectives.  

Our latest research, Crimson Echo, shifts the lens accordingly. Instead of dissecting campaigns, malware families, or actor labels as discrete events, the threat research team analyzed Chinese‑nexus activity as a continuum of behaviors over time. That broader view reveals how these operators position themselves within environments: quietly, patiently, and persistently—often preparing the ground long before any recognizable “incident” occurs.  

How Chinese-nexus cyber threats have changed over time

Chinese-nexus cyber activity has evolved in four phases over the past two decades. This ranges from early, high-volume operations in the 1990s and early 2000s to more structured, strategically-aligned activity in the 2010s, and now toward highly adaptive, identity-centric intrusions.  

Today’s phase is defined by scale, operational restraint, and persistence. Attackers are establishing access, evaluating its strategic value, and maintaining it over time. This reflects a broader shift: cyber operations are increasingly integrated into long-term economic and geopolitical strategies. Access to digital environments, specifically those tied to critical national infrastructure, supply chains, and advanced technology, has become a form of strategic leverage for the long-term.  

How Darktrace analysts took a behavioral approach to a complex problem

One of the challenges in analyzing nation-state cyber activity is attribution. Traditional approaches often rely on tracking specific threat groups, malware families, or infrastructure. But these change constantly, and in the case of Chinese-nexus operations, they often overlap.

Crimson Echo is the result of a retrospective analysis of three years of anomalous activity observed across the Darktrace fleet between July 2022 and September 2025. Using behavioral detection, threat hunting, open-source intelligence, and a structured attribution framework (the Darktrace Cybersecurity Attribution Framework), the team identified dozens of medium- to high-confidence cases and analyzed them for recurring operational patterns.  

This long-horizon, behavior-centric approach allows Darktrace to identify consistent patterns in how intrusions unfold, reinforcing that behavioral patterns that matter.  

What the data shows

Several clear trends emerged from the analysis:

  • Targeting is concentrated in strategically important sectors. Across the dataset, 88% of intrusions occurred in organizations classified as critical infrastructure, including transportation, critical manufacturing, telecommunications, government, healthcare, and Information Technology (IT) services.  
  • Strategically important Western economies are a primary focus. The US alone accounted for 22.5% of observed cases, and when combined with major European economies including Germany, Italy, Spain and the UK, over half of all intrusions (55%) were concentrated in these regions.  
  • Nearly 63% of intrusions of intrusions began with the exploitation of internet-facing systems, reinforcing the continued risk posed by externally exposed infrastructure.  

Two models of cyber operations

Across the dataset, Chinese-nexus activity followed two operational models.  

The first is best described as “smash and grab.” These are short-horizon intrusions optimized for speed. Attackers move quickly – often exfiltrating data within 48 hours – and prioritize scale over stealth. The median duration of these compromises is around 10 days. It’s clear they are willing to risk detection for short-term gain.  

The second is “low and slow.” These operations were less prevalent in the dataset, but potentially more consequential. Here, attackers prioritize persistence, establishing durable access through identity systems and legitimate administrative tools, so they can maintain access undetected for months or even years. In one notable case, the actor had fully compromised the environment and established persistence, only to resurface in the environment more than 600 days after. The operational pause underscores both the depth of the intrusion and the actor’s long‑term strategic intent. This suggests that cyber access is a strategic asset to preserve and leverage over time, and we observed these attacks most often inin sectors of the high strategic importance.  

It’s important to note that the same operational ecosystem can employ both models concurrently, selecting the appropriate model based on target value, urgency, intended access. The observation of a “smash and grab” model should not be solely interpreted as a failure of tradecraft, but instead an operational choice likely aligned with objectives. Where “low and slow” operations are optimized for patience, smash and grab is optimized for speed; both seemingly are deliberate operational choices, not necessarily indicators of capability.  

Rethinking cyber risk

For many organizations, cyber risk is still framed as a series of discrete events. Something happens, it is detected and contained, and the organization moves on. But persistent access, particularly in deeply interconnected environments that span cloud, identity-based SaaS and agentic systems, and complex supply chain networks, creates a major ongoing exposure risk. Even in the absence of disruption or data theft, that access can provide insight into operations, dependencies, and strategic decision-making. Cyber risk increasingly resembles long-term competitive intelligence.  

This has impact beyond the Security Operations Center. Organizations need to shift how they think about governance, visibility, and resilience, and treat cyber exposure as a structural business risk instead of an incident response challenge.  

What comes next

The goal of this research is to provide a clearer understanding of how these operations work, so defenders can recognize them earlier and respond more effectively. That includes shifting from tracking indicators to understanding behaviors, treating identity providers as critical infrastructure risks, expanding supplier oversight, investing in rapid containment capabilities, and more.  

Learn more about the findings of Darktrace’s latest research, Crimson Echo: Understanding Chinese-nexus Cyber Operations Through Behavioral Analysis, by downloading the full report and summaries for business leaders, CISOs, and SOC analysts here.  

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

Blog

/

Proactive Security

/

April 1, 2026

AI-powered security for a rapidly growing grocery enterprise

Default blog imageDefault blog image

Protecting a complex, fast-growing retail organization

For this multi-banner grocery holding organization, cybersecurity is considered an essential business enabler, protecting operations, growth, and customer trust. The organization’s lean IT team manages a highly distributed environment spanning corporate offices, 100+ stores, distribution centers and  thousands of endpoints, users, and third-party connections.

Mergers and acquisitions fueled rapid growth, but they also introduced escalating complexity that constrained visibility into users, endpoints, and security risks inherited across acquired environments.

Closing critical visibility gaps with limited resources

Enterprise-wide visibility is a top priority for the organization, says the  Vice President of Information Technology. “We needed insights beyond the perimeter into how users and devices were behaving across the organization.”

A security breach that occurred before the current IT leadership joined the company reinforced the urgency and elevated cybersecurity to an executive-level priority with a focus on protecting customer trust. The goal was to build a multi-layered security model that could deliver autonomous, enterprise-wide protection without adding headcount.

Managing cyber risk in M&A

Mergers and acquisitions are central to the grocery holding company’s growth strategy. But each transaction introduces new cyber risk, including inherited network architectures, inconsistent tooling, excessive privileges, and remnants of prior security incidents that were never fully remediated.

“Our M&A targets range from small chains with a single IT person and limited cyber tools to large chains with more developed IT teams, toolsets and instrumentation,” explains the VP of IT. “We needed a fast, repeatable, and reliable way to assess cyber risk before transactions closed.”

AI-driven security built for scale, speed, and resilience

Rather than layering additional point tools onto an already complex environment, the retailer adopted the Darktrace ActiveAI Security Platform™ in 2020 as part of a broader modernization effort to improve resilience, close visibility gaps, and establish a security foundation that could scale with growth.

“Darktrace’s AI-driven approach provided the ideal solution to these challenges,” shares the VP of IT. “It has empowered our organization to maintain a robust security strategy, ensuring the protection of our network and the smooth operation of our business.”

Enterprise-wide visibility into traffic  

By monitoring both north-south and east-west traffic and applying Self-Learning AI, Darktrace develops a dynamic understanding of how users and devices normally behave across locations, roles, and systems.

“Modeling normal behavior across the environment enables us to quickly spot behavior that doesn’t fit. Even subtle changes that could signal a threat but appear legitimate at first glance,” explains the VP of IT.

Real-time threat containment, 24/7

Adopting autonomous response has created operational breathing room for the security team, says the company’s Cybersecurity  Engineer.

“Early on, we enabled full Darktrace autonomous mode and we continue to do so today,” shares the IT Security Architect. “Allowing the technology to act first gives us the time we need to investigate incidents during business hours without putting the business at risk.”

Unified, actionable view of security ecosystem

The grocery retailer integrated Darktrace with its existing security ecosystem of firewalls, vulnerability management tools, and endpoint detection and response, and the VP of IT described the adoption process as “exceptionally smooth.”

The team can correlate enterprise-wide security data for a unified and actionable picture of all activity and risk. Using this “single pane of glass” approach, the retailer trains Level 1 and Level 2 operations staff to assist with investigations and user follow-ups, effectively extending the reach of the security function without expanding headcount.

From reactive defense to security at scale

With Darktrace delivering continuous visibility, autonomous containment, and integrated security workflows, the organization has strengthened its cybersecurity posture while improving operational efficiency. The result is a security model that not only reduces risk, but also supports growth, resilience, and informed decision-making at the business level.

Faster detection, faster resolution

With autonomous detection and response, the retailer can immediately contain risk while analysts investigate and validate activity. With this approach, the company can maintain continuous protection even outside business hours and reduce the chance of lateral spread across systems or locations.

Enterprise-grade protection with a lean team

From cloud environments to clients to SaaS collaboration tools, Darktrace provides holistic autonomous AI defense, processing petabytes of the organization’s network traffic and investigating millions of individual events that could be indicative of a wider incident.

Today, Darktrace autonomously conducts the majority of all investigations on behalf of the IT team, escalating only a tiny fraction for analyst review. The impact has been profound, freeing analysts from endless alerts and hours of triage so they can focus on more valuable, proactive, and gratifying work.

“From an operational perspective, Darktrace gives us time back,” says the Cybersecurity Engineer. More importantly, says the VP of IT, “it gives us peace of mind that we’re protected even if we’re not actively monitoring every alert.”

A strategic input for M&A decision-making

One of the most strategic outcomes has been the role of cybersecurity on M&A. 90 days prior to closing a transaction, the security team uses Darktrace alongside other tools to perform a cyber risk assessment of the potential acquisition. “Our approach with Darktrace has consistently identified gaps and exposed risks,” says the VP of IT, including:

  • Remnants of previous incidents that were never fully remediated
  • Network configurations with direct internet exposure
  • Excessive administrative privileges in Active Directory or on critical hosts

While security findings may not alter deal timelines, the VP of IT says they can have enormous business implications. “With early visibility into these risks, we can reduce exposure to inherited cyber threats, strengthen our position during negotiations, and establish clear remediation requirements.”

A security strategy built to evolve with the business

As the holding group expands its cloud footprint, it will extend Darktrace protections into Azure, applying the same AI-driven visibility and autonomous response to cloud workloads. The VP of IT says Darktrace's evolving capabilities will be instrumental in addressing the organization’s future cybersecurity needs and ability to adapt to the dynamic nature of cloud security.

“With Darktrace’s AI-driven approach, we have moved beyond reactive defense, establishing a resilient security foundation for confident expansion and modernization.”

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI