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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
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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

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May 21, 2025

Evaluating Email Security: How to Select the Best Solution for Your Organization

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When evaluating email security solutions, it’s crucial to move beyond marketing claims and focus on real-world performance. One of the most effective ways to achieve this is through an A/B comparison approach – a side-by-side evaluation of vendors based on consistent, predefined criteria.

This method cuts through biases, reveals true capability differences, and ensures that all solutions are assessed on a level playing field. It’s not just about finding an objectively good solution – it’s about finding the best solution for your organization’s specific needs.

An A/B comparison approach is particularly effective for three main reasons:

  1. Eliminates bias: By comparing solutions under identical conditions, it’s easier to spot differences in performance without the fog of marketing jargon.
  2. Highlights real capabilities: Direct side-by-side testing exposes genuine strengths and weaknesses, making it easier to judge which features are impactful versus merely decorative.
  3. Encourages objective decision-making: This structured method reduces emotional or brand-driven decisions, focusing purely on metrics and performance.

Let’s look at the key factors to consider when setting up your evaluation to ensure a fair, accurate, and actionable comparison.

Deployment: Setting the stage for fair evaluation

To achieve a genuine comparison, deployment must be consistent across all evaluated solutions:

  • Establish the same scope: All solutions should be granted identical visibility across relevant tenants and domains to ensure parity.
  • Set a concrete timeline: Deploy and test each solution with the same dataset, at the same points in time. This allows you to observe differences in learning periods and adaptive capabilities.

Equal visibility and synchronized timelines prevent discrepancies that could skew your understanding of each vendor’s true capabilities. But remember – quicker results might not equal better learning or understanding!

Tuning and configurations: Optimizing for real-world conditions

Properly tuning and configuring each solution is critical for fair evaluation:

  • Compare on optimal performance: Consult with each vendor to understand what optimal deployment looks like for their solution, particularly if machine learning is involved.
  • Consider the long term: Configuration adjustments should be made with long-term usage in mind. Short-term fixes can mask long-term challenges.
  • Data visibility: Ensure each solution can retain and provide search capabilities on all data collected throughout the evaluation period.

These steps guarantee that you are comparing fully optimized versions of each platform, not underperforming or misconfigured ones.

Evaluation: Applying consistent metrics

Once deployment and configurations are aligned, the evaluation itself must be consistent, to prevent unfair scoring and help to identify true differences in threat detection and response capabilities.

  • Coordinate your decision criteria: Ensure all vendors are measured against the same set of criteria, established before testing begins.
  • Understand vendor threat classification: Each vendor may have different ways of classifying threats, so be sure to understand these nuances.
  • Maintain communication: If results seem inaccurate, engage with the vendors. Their response and remediation capabilities are part of the evaluation.

Making a decision: Look beyond the metrics

When it comes to reviewing the performance of each solution, it’s important to both consider and look beyond the raw data. This is about choosing the solution that best aligns with your specific business needs, which may include factors and features not captured in the results.

  • Evaluate based on results: Consider accuracy, threats detected, precision, and response effectiveness.
  • Evaluate beyond results: Assess the overall experience, including support, integrations, training, and long-term alignment with your security strategy.
  • Review and communicate: Internally review the findings and communicate them back to the vendors.

Choosing the right email security solution isn’t just about ticking boxes, it’s about strategic alignment with your organization’s goals and the evolving threat landscape. A structured, A/B comparison approach will help ensure that the solution you select is truly the best fit.

For a full checklist of the features and capabilities to compare, as well as how to perform a commercial and technical evaluation, check out the full Buyer’s Checklist for Evaluating Email Security.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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May 21, 2025

Adapting to new USCG cybersecurity mandates: Darktrace for ports and maritime systems

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What is the Marine Transportation System (MTS)?

Marine Transportation Systems (MTS) play a substantial roll in U.S. commerce, military readiness, and economic security. Defined as a critical national infrastructure, the MTS encompasses all aspects of maritime transportation from ships and ports to the inland waterways and the rail and roadways that connect them.

MTS interconnected systems include:

  • Waterways: Coastal and inland rivers, shipping channels, and harbors
  • Ports: Terminals, piers, and facilities where cargo and passengers are transferred
  • Vessels: Commercial ships, barges, ferries, and support craft
  • Intermodal Connections: Railroads, highways, and logistics hubs that tie maritime transport into national and global supply chains

The Coast Guard plays a central role in ensuring the safety, security, and efficiency of the MTS, handling over $5.4 trillion in annual economic activity. As digital systems increasingly support operations across the MTS, from crane control to cargo tracking, cybersecurity has become essential to protecting this lifeline of U.S. trade and infrastructure.

Maritime Transportation Systems also enable international trade, making them prime targets for cyber threats from ransomware gangs to nation-state actors.

To defend against growing threats, the United States Coast Guard (USCG) has moved from encouraging cybersecurity best practices to enforcing them, culminating in a new mandate that goes into effect on July 16, 2025. These regulations aim to secure the digital backbone of the maritime industry.

Why maritime ports are at risk

Modern ports are a blend of legacy and modern OT, IoT, and IT digitally connected technologies that enable crane operations, container tracking, terminal storage, logistics, and remote maintenance.

Many of these systems were never designed with cybersecurity in mind, making them vulnerable to lateral movement and disruptive ransomware attack spillover.

The convergence of business IT networks and operational infrastructure further expands the attack surface, especially with the rise of cloud adoption and unmanaged IoT and IIoT devices.

Cyber incidents in recent years have demonstrated how ransomware or malicious activity can halt crane operations, disrupt logistics, and compromise safety at scale threatening not only port operations, but national security and economic stability.

Relevant cyber-attacks on maritime ports

Maersk & Port of Los Angeles (2017 – NotPetya):
A ransomware attack crippled A.P. Moller-Maersk, the world’s largest shipping company. Operations at 17 ports, including the Port of Los Angeles, were halted due to system outages, causing weeks of logistical chaos.

Port of San Diego (2018 – Ransomware Attack):
A ransomware attack targeted the Port of San Diego, disrupting internal IT systems including public records, business services, and dockside cargo operations. While marine traffic was unaffected, commercial activity slowed significantly during recovery.

Port of Houston (2021 – Nation-State Intrusion):
A suspected nation-state actor exploited a known vulnerability in a Port of Houston web application to gain access to its network. While the attack was reportedly thwarted, it triggered a federal investigation and highlighted the vulnerability of maritime systems.

Jawaharlal Nehru Port Trust, India (2022 – Ransomware Incident):
India’s largest container port experienced disruptions due to a ransomware attack affecting operations and logistics systems. Container handling and cargo movement slowed as IT systems were taken offline during recovery efforts.

A regulatory shift: From guidance to enforcement

Since the Maritime Transportation Security Act (MTSA) of 2002, ports have been required to develop and maintain security plans. Cybersecurity formally entered the regulatory fold in 2020 with revisions to 33 CFR Part 105 and 106, requiring port authorities to assess and address computer system vulnerabilities.

In January 2025, the USCG finalized new rules to enforce cybersecurity practices across the MTS. Key elements include (but are not limited to):

  • A dedicated cyber incident response plan (PR.IP-9)
  • Routine cybersecurity risk assessments and exercises (ID.RA)
  • Designation of a cybersecurity officer and regular workforce training (section 3.1)
  • Controls for access management, segmentation, logging, and encryption (PR.AC-1:7)
  • Supply chain risk management (ID.SC)
  • Incident reporting to the National Response Center

Port operators are encouraged to align their programs with the NIST Cybersecurity Framework (CSF 2.0) and NIST SP 800-82r3, which provide comprehensive guidance for IT and OT security in industrial environments.

How Darktrace can support maritime & ports

Unified IT + OT + Cloud coverage

Maritime ports operate in hybrid environments spanning business IT systems (finance, HR, ERP), industrial OT (cranes, gates, pumps, sensors), and an increasing array of cloud and SaaS platforms.

Darktrace is the only vendor that provides native visibility and threat detection across OT/IoT, IT, cloud, and SaaS environments — all in a single platform. This means:

  • Cranes and other physical process control networks are monitored in the same dashboard as Active Directory and Office 365.
  • Threats that start in the cloud (e.g., phishing, SaaS token theft) and pivot or attempt to pivot into OT are caught early — eliminating blind spots that siloed tools miss.

This unification is critical to meeting USCG requirements for network-wide monitoring, risk identification, and incident response.

AI that understands your environment. Not just known threats

Darktrace’s AI doesn’t rely on rules or signatures. Instead, it uses Self-Learning AI TM that builds a unique “pattern of life” for every device, protocol, user, and network segment, whether it’s a crane router or PLC, SCADA server, Workstation, or Linux file server.

  • No predefined baselines or manual training
  • Real-time anomaly detection for zero-days, ransomware, and supply chain compromise
  • Continuous adaptation to new devices, configurations, and operations

This approach is critical in diverse distributed OT environments where change and anomalous activity on the network are more frequent. It also dramatically reduces the time and expertise needed to classify and inventory assets, even for unknown or custom-built systems.

Supporting incident response requirements

A key USCG requirement is that cybersecurity plans must support effective incident response.

Key expectations include:

  • Defined response roles and procedures: Personnel must know what to do and when (RS.CO-1).
  • Timely reporting: Incidents must be reported and categorized according to established criteria (RS.CO-2, RS.AN-4).
  • Effective communication: Information must be shared internally and externally, including voluntary collaboration with law enforcement and industry peers (RS.CO-3 through RS.CO-5).
  • Thorough analysis: Alerts must be investigated, impacts understood, and forensic evidence gathered to support decision-making and recovery (RS.AN-1 through RS.AN-5).
  • Swift mitigation: Incidents must be contained and resolved efficiently, with newly discovered vulnerabilities addressed or documented (RS.MI-1 through RS.MI-3).
  • Ongoing improvement: Organizations must refine their response plans using lessons learned from past incidents (RS.IM-1 and RS.IM-2).

That means detections need to be clear, accurate, and actionable.

Darktrace cuts through the noise using AI that prioritizes only high-confidence incidents and provides natural-language narratives and investigative reports that explain:

  • What’s happening, where it’s happening, when it’s happening
  • Why it’s unusual
  • How to respond

Result: Port security teams often lean and multi-tasked can meet USCG response-time expectations and reporting needs without needing to scale headcount or triage hundreds of alerts.

Built-for-edge deployment

Maritime environments are constrained. Many traditional SaaS deployment types often are unsuitable for tugboats, cranes, or air-gapped terminal systems.

Darktrace builds and maintains its own ruggedized, purpose-built appliances and unique virtual deployment options that:

  • Deploy directly into crane networks or terminal enclosures
  • Require no configuration or tuning, drop-in ready
  • Support secure over-the-air updates and fleet management
  • Operate without cloud dependency, supporting isolated and air-gapped systems

Use case: Multiple ports have been able to deploy Darktrace directly into the crane’s switch enclosure, securing lateral movement paths without interfering with the crane control software itself.

Segmentation enforcement & real-time threat containment

Darktrace visualizes real-time connectivity and attack pathways across IT, OT, and IoT it and integrates with firewalls (e.g., Fortinet, Cisco, Palo Alto) to enforce segmentation using AI insights alongside Darktrace’s own native autonomous and human confirmed response capabilities.

Benefits of autonomous and human confirmed response:

  • Auto-isolate rogue devices before the threat can escalate
  • Quarantine a suspicious connectivity with confidence operations won’t be halted
  • Autonomously buy time for human responders during off-hours or holidays
  • This ensures segmentation isn't just documented but that in the case of its failure or exploitation responses are performed as a compensating control

No reliance on 3rd parties or external connectivity

Darktrace’s supply chain integrity is a core part of its value to critical infrastructure customers. Unlike solutions that rely on indirect data collection or third-party appliances, Darktrace:

  • Uses in-house engineered sensors and appliances
  • Does not require transmission of data to or from the cloud

This ensures confidence in both your cyber visibility and the security of the tools you deploy.

See examples here of how Darktrace stopped supply chain attacks:

Readiness for USCG and Beyond

With a self-learning system that adapts to each unique port environment, Darktrace helps maritime operators not just comply but build lasting cyber resilience in a high-threat landscape.

Cybersecurity is no longer optional for U.S. ports its operationally and nationally critical. Darktrace delivers the intelligence, automation, and precision needed to meet USCG requirements and protect the digital lifeblood of the modern port.

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About the author
Daniel Simonds
Director of Operational Technology
Your data. Our AI.
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