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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 26, 2026

The CIP-015 Countdown: What Utilities Should Be Doing Before October 2028

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CIP-015 what you need to know

The electric sector already knows CIP-015 is coming. The better question is whether utilities are using the time before October 1, 2028 to build an Internal Network Security Monitoring program that is defensible, auditable, and operationally useful.

I have spent most of my OT cybersecurity career around the power sector, from early NERC CIP program work as an asset owner, to consulting with utilities ranging from small municipalities and rural cooperatives to some of the largest power companies in the country, to now working with technology that helps organizations improve visibility and detection across IT and OT. One lesson has been consistent across all of those roles: compliance is not just about having a control in place. It is about being able to prove the control works.

That is where CIP-015 becomes important.

The standard is not simply asking utilities to deploy a tool inside the Electronic Security Perimeter and call the job done. CIP-015 is about improving the probability of detecting anomalous or unauthorized network activity so that organizations can improve response and recovery from an attack. That purpose is directly stated in the standard itself. (NERC)

The real work between now and October 2028 is not just buying technology. It is building an INSM capability that can collect the right data, detect meaningful activity, support evaluation, retain the right evidence, and protect that evidence from unauthorized deletion or modification.

Why CIP-015 exists

CIP-015 exists because perimeter security alone does not solve the internal visibility problem.

For years, many CIP controls have focused heavily on access management, segmentation, patching, logging, training, and other security practices that help reduce the likelihood of unauthorized access. Those controls still matter. But they do not fully answer what happens after an attacker, insider, compromised vendor account, misused credential, or malicious activity is already operating inside a trusted environment.

NERC’s technical rationale explains that Internal Network Security Monitoring focuses on the collection and analysis of network communications inside a “trust zone,” such as an ESP. In other words, CIP-015 is not only about defending the edge. It is about understanding what is happening inside the environment once traffic is already within the trusted zone. (NERC)

That is the internal visibility gap utilities need to close.

Why traditional security monitoring does not fully satisfy CIP-015

One mistake utilities should avoid is assuming that existing security event monitoring automatically solves CIP-015.

Many organizations already have logging programs tied to CIP-007, SIEM use cases, host-level security events, authentication logs, malware alerts, and incident response workflows. Those capabilities remain valuable, but they are not the same as Internal Network Security Monitoring.

Security event monitoring often tells you what happened on or to a system. INSM is intended to help show what is happening between systems, across network communications, devices, connections, and internal traffic patterns. That distinction is especially important in OT environments where adversaries may use legitimate pathways, valid credentials, native protocols, remote access, engineering workstations, or trusted systems to move inside the environment.

CIP-015 pushes utilities toward a different level of visibility: not just “did a system log something,” but “can we see and evaluate anomalous or unauthorized activity occurring inside the ESP?”

What CIP-015 requires

At a high level, CIP-015-1 requires three core capabilities.

Requirement R1: Monitoring internal network activity  

First, under Requirement R1, Responsible Entities must implement, using a risk-based rationale, network data feeds to monitor network activity, including connections, devices, and network communications. They must also implement one or more methods to detect anomalous network activity using those feeds, and one or more methods to evaluate detected anomalous activity to determine further actions.

Requirement R2: Retaining INSM data for investigations

Second, under Requirement R2, entities must retain INSM data associated with anomalous network activity at least until the related evaluation and action are complete. The standard also notes that entities are not required to retain INSM data that is not relevant to detected anomalous activity.

Requirement R3: Protecting monitoring data from tampering

Third, under Requirement R3, entities must protect INSM data collected for R1 and retained for R2 from unauthorized deletion or modification.

Those requirements may sound straightforward, but implementation is where the challenge begins.

What should utilities be asking themselves for CIP-015?

  • Where are we collecting network data inside the ESP, and why are those feeds defensible?
  • What methods are we using to detect anomalous network activity?
  • How do we distinguish meaningful anomalous behavior from normal operational change?
  • Who evaluates detections, and how are decisions documented?
  • What data is retained, and how is it protected from unauthorized deletion or modification?
  • Can we produce evidence that proves this process has worked over time?

Those answers matter because auditors will not be looking for marketing claims. They will be looking for evidence.

Why anomaly detection is central to CIP-015 compliance

One of the most important parts of CIP-015 is also one of the easiest to oversimplify: the word anomalous.

NERC’s technical rationale provides useful context. It explains that, as used in CIP-015, “anomalous” refers to unexpected, undesired, unusual, or undetermined network traffic. It also makes clear that the term does not refer to any single proprietary technology commonly marketed as “anomaly detection.”

Understanding static baselines vs true anomaly detection

A static baseline is not the same thing as meaningful anomaly detection. If a platform observes traffic for a limited period of time, assumes that observed behavior is “normal,” and then flags future deviations without deeper context, the result can be noisy, brittle, and operationally frustrating.

In real OT environments, “normal” is not fixed. Maintenance windows, vendor access, failovers, engineering changes, testing activity, backup jobs, and operational shifts can all change behavior. Detection has to keep learning and understand context. Otherwise, the organization may end up with alerts that are technically anomalous but not practically useful.

CIP-015 is not just about producing anomalies. It is about producing meaningful detections that can be evaluated, documented, and acted upon.

What should utilities consider when looking for anomaly detection tools

Some technologies were built around behavioral analysis and anomaly detection long before CIP-015 existed. What practitioners should look for is if the technology behind the phrase can identify meaningful deviations, provide context, reduce noise, and support the evaluation and evidence expectations of the standard.

Utilities should be cautious of vendor positioning that treats “anomaly” as a simple compliance keyword. This is especially important when evaluating tools historically built around signature-based, threat-based, or rule-based detection methods that are now being positioned as anomaly detection because CIP-015 uses the term.

A platform does not solve CIP-015 simply because it can baseline traffic or generate alerts when something changes.

The question is not: Can this tool create alerts?

The question is: Can this tool identify meaningful anomalous activity with enough context, prioritization, and evidence to support evaluation and response?

Why evidence and audit readiness matter for CIP-015

In NERC CIP, the control is only part of the story. Evidence is the part that proves the control existed, worked, and was followed.

That is why CIP-015 readiness should not be treated as a simple deployment project. It should be treated as a compliance operations and evidence program.

What auditors will expect utilities to prove

For R1, examples of evidence include documentation of network data feeds and the risk-based rationale for selecting them, anomalous network detection events, INSM configuration settings, communication baselines or other detection methods, methods used to evaluate anomalous activity, and actions taken in response to detected anomalies.

For R2, evidence may include documentation of the retention process, system configurations, or system-generated reports showing retention timelines sufficient to support evaluation. For R3, evidence may include documentation showing how INSM data is protected from unauthorized deletion or modification.

Common evidence gaps that can create compliance risk

If an entity implements a platform that generates noisy detections, lacks context, does not retain the right data, cannot demonstrate how data is protected, or cannot produce useful audit evidence, the issue may not become obvious until much later. By then, an organization may discover during an audit that it cannot prove what it thought it had implemented.

That is a bad place to be.

CIP evidence gaps can create exposure that goes back over time, not just to the day the audit finding is discovered. This is why utilities need to validate the process early. Do not wait until an audit cycle to find out whether your INSM approach can stand up to scrutiny.

How utilities should prepare for CIP-015 before 2028

October 2028 may sound far away, but in utility planning terms, it is not.

Utilities should already be moving through a structured readiness process.

Assessing internal network visibility across trusted environments

Start with scope. Identify the applicable High and Medium Impact BES Cyber Systems, the relevant ESPs, and the environments where INSM requirements will apply. Then map current visibility. Where do you already have useful network monitoring? Where are you relying mostly on logs, perimeter controls, or assumptions? Where do you have limited east-west visibility inside trusted environments?

Building a defensible network data feed strategy

Next, define the network data feed strategy. CIP-015 requires a risk-based rationale, so the organization should be able to explain why specific feeds were selected and how they support detection of anomalous activity across relevant connections, devices, and communications.

Validating anomaly detection workflows

Then validate the detection method. This is where utilities need to go deeper than vendor claims. Ask how the platform identifies anomalous activity. Ask how it reduces noise. Ask what context is provided for evaluation. Ask how it handles changes in normal operations. Ask what evidence is retained and how that evidence can be produced.

Testing evidence retention and protection processes

After that, build the evaluation workflow. Who reviews detections? How are anomalies classified as benign, abnormal but not suspicious, suspicious, or potentially malicious? When does an event move into CIP-008 incident response? What documentation is created during that process?

Finally, test evidence production. Utilities should be able to show detection records, configuration settings, evaluation notes, response actions, retention records, and data protection controls before an auditor asks for them.

Where Darktrace Fits into CIP-015

This is where technology matters, but only as part of the broader program.

Darktrace was built on self-learning anomaly detection long before CIP-015 created a new compliance driver around anomalous network activity. Its value is rooted in continuous behavioral understanding, multiple analytical techniques, and the ability to identify meaningful deviations across complex IT and OT environments. That matters because CIP-015 requires more than basic alerting. It requires detection that supports evaluation, evidence, and action.

This IT and OT visibility is especially important in power utility environments. High and Medium Impact environments are not made up only of industrial protocols and field devices. Control centers, operational workstations, engineering workstations, servers, remote access systems, domain services, printers, and other enterprise-class assets often sit inside or adjacent to critical operational environments. A useful INSM capability should understand a wide range of communications across both IT and OT, not only traditional industrial protocols like Modbus, DNP3, or IEC 61850.

That distinction matters because “protocol support” can mean very different things. Identifying that a protocol is present is not the same as performing deeper packet analysis that can provide behavioral context, richer protocol understanding, and meaningful detection across the communications actually used inside the environment. For CIP-015, utilities should be asking whether a platform can help evaluate activity across both enterprise and industrial communications, because real power utility environments are rarely “OT-only.”

This is also why utilities should look carefully at how vendors use the word “anomaly.” Some platforms were designed around behavioral understanding and anomaly detection long before CIP-015 created a new compliance driver. Others may now be adopting the language because the standard uses the term. The difference matters. Utilities should ask whether the platform’s detection approach is foundational to the technology, or simply a new label applied to existing signature-based, threat-based, or rule-based methods.

In OT environments, detection quality matters. Utilities do not need more noise. They need visibility into internal communications, confidence in what is normal, context when something changes, and prioritization that helps security and operations teams focus on what matters.

A strong INSM program should help utilities move from raw monitoring to operational confidence. It should support east-west visibility, better anomaly evaluation, defensible evidence retention, protection of monitoring data, and alignment between compliance and security outcomes.

That is the right way to think about CIP-015.

Not as “deploy a tool and move on.”But as “build a capability that can be trusted, operated, and proven.”

CIP-015 is about proving your INSM capability works

The CIP-015 countdown is real, but the countdown itself is not the whole story.

The real story is what utilities do with the time that remains.

Organizations that treat CIP-015 as a checkbox may be able to say they deployed something. But organizations that treat it as an opportunity to close the internal visibility gap will gain something much more valuable: better detection, better response, better evidence, and stronger operational resilience.

The question utilities should be asking now is not whether they can produce more alerts before October 2028.

The question is whether they can prove their INSM capability actually works.

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About the author
Jeffrey Macre
Principal Industrial Security Solutions Architect

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Email

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May 26, 2026

Journey of a Threat: How Multi-Layered AI Works in Darktrace / EMAIL

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Darktrace / EMAIL is an implementation of the Darktrace methodology – a multi-layered AI system built into a single product. As with other Darktrace products, Darktrace / EMAIL learns the expected behaviours of an organization and its employees to identify novel threats and anomalous activity.

The diagram below represents the architecture of Darktrace / EMAIL’s multi-layered AI: a structured visualization of how intelligence is built, step by step, from raw data to actionable insight. Each layer plays a distinct role, feeding into the next: collecting data, understanding behaviour, analysing intent, making decisions, and presenting clear outcomes.

It all starts with an email

In this blog, we’ll follow a malicious email as it passes through the Darktrace / EMAIL system, showing exactly what happens as it travels through each layer of the pyramid, from basic data extraction to AI-powered metric creation, and finally deciding on any autonomous actions.

Let’s take this example email. As an end-user, you can see that this is an obvious extortion attempt where an adversary is threatening legal action if money isn’t paid within 24 hours, but how does Darktrace figure that out?

Part 1: Data Gathering

Processing of an email begins on point-of-transit for all inbound, outbound, or lateral emails. The first step is to extract information directly. This includes taking information from the headers (such as sending and receiving addresses, sender IP address, routing, and authentication protocols), as well as extraction of raw HTML and CSS data from the email itself.

This directly extracted information only allows for immediate surface level analysis, such as identifying signature-based attacks (known malicious addresses / domains), but is insufficient for identifying novel threats, complex attacks, or potential email or vendor compromise. This is where Darktrace’s AI analysis shines.

In this example, the SPF, DKIM, and DMARC authentication all passed successfully, showing that even malicious emails can still bypass these signature-based checks. Even with this success, Darktrace will continue to analyse the email.

Diving deeper into the technical information, we can see further information extracted from the headers, including aggregations from the header information, historical calculations such as the frequency and volume of emails to and from a particular domain, and much more.

Part 2: Social Graphing

Social Graphing involves the analysis of sending and receiving behaviours of different mailboxes to create peer-groups. Mailboxes who often send and receive to and from the same mailboxes, or exhibit other correlated behaviours, will be clustered together using a collection of unsupervised AI clustering systems. These groups may represent uses in the same teams who perform similar activity, groups of external facing mailboxes which often receive unsolicited emails, or groups of VIP users (such as C-suite or executives).

Social graphing is an essential component of Darktrace’s pattern of life analysis. This clustering allows Darktrace to understand the responsibilities of individuals – for example, behaviours which are anomalous for one group of users may be completely expected of another group.

In our example, the email was sent to 3 different users within the organization. As part of the social graphing, an “Association Anomaly” is calculated which indicates the likelihood that these users would receive emails from this user or domain, based on historical patterns.

Part 3: Metric Calculation

Metrics are calculated for every email, representing more complex characteristics of an email which can’t be directly extracted. Darktrace / EMAIL features over 1000 unique metrics, calculated both algorithmically and using an ensemble of AI systems.

Algorithmically calculated (non-AI) metrics include further historical calculations, and counts of features such as code blocks, and hidden text, to name a few.

AI-driven metrics include Inducement Classification which uses Natural Language Processing to identify potential phishing, solicitation, or extortion attempts; Named Entity Recognition to identify PII and other sensitive data within an email to support Data Loss Prevention; and many more.

We can follow our example email through this process and view the outcome of these metric calculations. Looking at the language metrics for this email, we can see that our email has reported a high extortion inducement, along with identification of banking information and language indicating urgency.

Part 4: Evaluation and Combination Engine (models)

Once all metrics have been calculated for an email, it gets sent to an evaluation and combination engine where the metrics are compared against blocks of logic to determine if an email contains a threat. One key model which alerted for this example message was a model to tag and block extortion attempts.

Since our example email has a high inducement score for extortion, along the presence of a bitcoin wallet address in the message, this model alerts. When a model in the engine is activated, actions are taken – in this case adding a tag to the email to flag it as extortion in the console and hold the email to prevent it from reaching the end-user mailbox.

Part 5: Meta-Modelling and Actions

Once the models have been run, the actions are taken against the email. If the email hasn’t been blocked or held, this is the point where it will reach the end-user's mailbox.

In the Darktrace / EMAIL UI, all actions models which alerted for an email and actions taken as a result can be seen. At the top of this page, you can see the alert indicating an extortion attempt along with the action to hold the message.

Alongside this, a meta-classifier is used to calculate an overall anomaly score for each email, based on how much the email differs from the pattern of life for the user. The score of the email is boosted by any actions that have taken place.

Part 6: Campaign Clustering

All emails are passed through the Darktrace / EMAIL campaign clustering system. This system creates clusters based on related features within the emails to identify groups of emails with the same sender or intent.

In our case, the email was identified as part of a campaign, alongside other emails which were also identified as extortion attempts against a small group of recipients.

Email campaigns may have additional actions applied to them if the campaign is deemed malicious, and in this case, you can see that the autonomous response was to hold all emails in the campaign. This means that if an email manages to avoid being blocked in the evaluation and combination engine but gets identified as part of the campaign, the hold action will be applied to it retroactively.

Part 7: Cyber AI Analyst

Darktrace’s Cyber AI Analyst presents key information and anomaly indicators for each email, such as further information about authentication, specific metrics, or other identified anomalies and mismatches.

Cyber AI Analyst can also utilize data from Darktrace / EMAIL to enhance its investigation of incidents from other Darktrace products, correlating relevant information to build a fuller picture. More information about the Cyber AI Analyst is available in the Darktrace AI Arsenal.

Part 8: Data Presentation (UI)

Once all processing has taken place against the email, it is presented in the Darktrace / EMAIL UI. Here, members of the SOC team can investigate incidents and anomalies, interact with malicious emails to see why they were blocked, and much more.

Our email stands out here with its 100 anomaly score. Every email which passes through a Darktrace / EMAIL will undergo the same thorough and rigorous analysis to identify potential risks, apply autonomous actions where required, and will ultimately be assigned a score to be displayed here. By providing a single overall score in the UI, rather than presenting emails in full, Darktrace / EMAIL allows SOC teams to more easily identify which emails are most important to investigate, increasing efficiency and reducing alert fatigue.

Take the next step

Many email security tools on the market that claim to be AI-driven are in fact bolting AI onto attack-centric approaches, which rely on automating the identification of known threats. These approaches struggle, and will continue to struggle, with adapting to novel, AI-generated threats.

By analyzing every email within its deeply integrated, multi-layered AI system, Darktrace / EMAIL is able to identify the subtle threats that others miss. This depth not only improves detection accuracy, but enables confident, autonomous action, giving security teams clearer insight into AI outcomes and greater control while supporting users.

For a full deep dive into each stage of the AI system, check out the white paper: A Guide to the Multi-Layered AI in Darktrace / EMAIL

Learn more about securing AI in your enterprise.

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About the author
Jamie Bali
Technical Author (AI) Developer
Your data. Our AI.
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