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September 28, 2023

How Darktrace Stopped an Account Hijack Fast

Learn how Darktrace detected an account hijack within days of deployment. Discover the strategies used to protect against cyber threats.
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
Min Kim
Cyber Security Analyst
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28
Sep 2023

Cloud Migration Expanding the Attack Surface

Cloud migration is here to stay – accelerated by pandemic lockdowns, there has been an ongoing increase in the use of public cloud services, and Gartner has forecasted worldwide public cloud spending to grow around 20%, or by almost USD 600 billion [1], in 2023. With more and more organizations utilizing cloud services and moving their operations to the cloud, there has also been a corresponding shift in malicious activity targeting cloud-based software and services, including Microsoft 365, a prominent and oft-used Software-as-a-Service (SaaS).

With the adoption and implementation of more SaaS products, the overall attack surface of an organization increases – this gives malicious actors additional opportunities to exploit and compromise a network, necessitating proper controls to be in place. This increased attack surface can leave organization’s open to cyber risks like cloud misconfigurations, supply chain attacks and zero-day vulnerabilities [2]. In order to achieve full visibility over cloud activity and prevent SaaS compromise, it is paramount for security teams to deploy sophisticated security measures that are able to learn an organization’s SaaS environment and detect suspicious activity at the earliest stage.

Darktrace Immediately Detects Hijacked Account

In May 2023, Darktrace observed a chain of suspicious SaaS activity on the network of a customer who was about to begin their trial of Darktrace/Apps™ and Darktrace/Email™. Despite being deployed on the network for less than a week, Darktrace DETECT™ recognized that the legitimate SaaS account, belonging to an executive at the organization, had been hijacked. Darktrace/Email was able to provide full visibility over inbound and outbound mail and identified that the compromised account was subsequently used to launch an internal spear-phishing campaign.

If Darktrace RESPOND™ were enabled in autonomous response mode at the time of this compromise, it would have been able to take swift preventative action to disrupt the account compromise and prevent the ensuing phishing attack.

Account Hijack Attack Overview

Unusual External Sources for SaaS Credentials

On May 9, 2023, Darktrace/Apps detected the first in a series of anomalous activities performed by a Microsoft 365 user account that was indicative of compromise, namely a failed login from an external IP address located in Virginia.

Figure 1: The failed login notice, as seen in Darktrace/Apps. The notice includes additional context about the failed login attempt to the SaaS account.

Just a few minutes later, Darktrace observed the same user credential being used to successfully login from the same unusual IP address, with multi-factor authentication (MFA) requirements satisfied.

Figure 2: The “Unusual External Source for SaaS Credential Use” model breach summary, showing the successful login to the SaaS user account (with MFA), from the rare external IP address.

A few hours after this, the user credential was once again used to login from a different city in the state of Virginia, with MFA requirements successfully met again. Around the time of this activity, the SaaS user account was also observed previewing various business-related files hosted on Microsoft SharePoint, behavior that, taken in isolation, did not appear to be out of the ordinary and could have represented legitimate activity.

The following day, May 10, however, there were additional login attempts observed from two different states within the US, namely Texas and Florida. Darktrace understood that this activity was extremely suspicious, as it was highly improbable that the legitimate user would be able to travel over 2,500 miles in such a short period of time. Both login attempts were successful and passed MFA requirements, suggesting that the malicious actor was employing techniques to bypass MFA. Such MFA bypass techniques could include inserting malicious infrastructure between the user and the application and intercepting user credentials and tokens, or by compromising browser cookies to bypass authentication controls [3]. There have also been high-profile cases in the recent years of legitimate users mistakenly (and perhaps even instinctively) accepting MFA prompts on their token or mobile device, believing it to be a legitimate process despite not having performed the login themselves.

New Email Rule

On the evening of May 10, following the successful logins from multiple US states, Darktrace observed the Microsoft 365 user creating a new inbox rule, named “.’, in Microsoft Outlook from an IP located in Florida. Threat actors are often observed naming new email rules with single characters, likely to evade detection, but also for the sake of expediency so as to not expend any additional time creating meaningful labels.

In this case the newly created email rules included several suspicious properties, including ‘AlwaysDeleteOutlookRulesBlob’, ‘StopProcessingRules’ and “MoveToFolder”.

Firstly, ‘AlwaysDeleteOutlookRulesBlob’ suppresses or hides warning messages that typically appear if modifications to email rules are made [4]. In this case, it is likely the malicious actor was attempting to implement this property to obfuscate the creation of new email rules.

The ‘StopProcessingRules’ rule meant that any subsequent email rules created by the legitimate user would be overridden by the email rule created by the malicious actor [5]. Finally, the implementation of “MoveToFolder” would allow the malicious actor to automatically move all outgoing emails from the “Sent” folder to the “Deleted Items” folder, for example, further obfuscating their malicious activities [6]. The utilization of these email rule properties is frequently observed during account hijackings as it allows attackers to delete and/or forward key emails, delete evidence of exploitation and launch phishing campaigns [7].

In this incident, the new email rule would likely have enabled the malicious actor to evade the detection of traditional security measures and achieve greater persistence using the Microsoft 365 account.

Figure 3: Screenshot of the “New Email Rule” model breach. The Office365 properties associated with the newly modified Microsoft Outlook inbox rule, “.”, are highlighted in red.

Account Update

A few hours after the creation of the new email rule, Darktrace observed the threat actor successfully changing the Microsoft 365 user’s account password, this time from a new IP address in Texas. As a result of this action, the attacker would have locked out the legitimate user, effectively gaining full access over the SaaS account.

Figure 4: The model breach event log showing the user password and token change updates performed by the compromised SaaS account.

Phishing Emails

The compromised SaaS account was then observed sending a high volume of suspicious emails to both internal and external email addresses. Darktrace was able to identify that the emails attempting to impersonate the legitimate service DocuSign and contained a malicious link prompting users to click on the text “Review Document”. Upon clicking this link, users would be redirected to a site hosted on Adobe Express, namely hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/.

Adobe Express is a free service that allows users to create web pages which can be hosted and shared publicly; it is likely that the threat actor here leveraged the service to use in their phishing campaign. When clicked, such links could result in a device unwittingly downloading malware hosted on the site, or direct unsuspecting users to a spoofed login page attempting to harvest user credentials by imitating legitimate companies like Microsoft.

Figure 5: Screenshot of the phishing email, containing a malicious link hidden behind the “Review Document” text. The embedded link directs to a now-defunct page that was hosted on Adobe Express.

The malicious site hosted on Adobe Express was subsequently taken down by Adobe, possibly in response to user reports of maliciousness. Unfortunately though, platforms like this that offer free webhosting services can easily and repeatedly be abused by malicious actors. Simply by creating new pages hosted on different IP addresses, actors are able to continue to carry out such phishing attacks against unsuspecting users.

In addition to the suspicious SaaS and email activity that took place between May 9 and May 10, Darktrace/Email also detected the compromised account sending and receiving suspicious emails starting on May 4, just two days after Darktrace’s initial deployment on the customer’s environment. It is probable that the SaaS account was compromised around this time, or even prior to Darktrace’s deployment on May 2, likely via a phishing and credential harvesting campaign similar to the one detailed above.

Figure 6: Event logs of the compromised SaaS user, here seen breaching several Darktrace/Email model breaches on 4th May.

Darktrace Coverage

As the customer was soon to begin their trial period, Darktrace RESPOND was set in “human confirmation” mode, meaning that any preventative RESPOND actions required manual application by the customer’s security team.

If Darktrace RESPOND had been enabled in autonomous response mode during this incident, it would have taken swift mitigative action by logging the suspicious user out of the SaaS account and disabling the account for a defined period of time, in doing so disrupting the attack at the earliest possible stage and giving the customer the necessary time to perform remediation steps.  As it was, however, these RESPOND actions were suggested to the customer’s security team for them to manually apply.

Figure 7: Example of Darktrace RESPOND notices, in response to the anomalous user activity.

Nevertheless, with Darktrace/Apps in place, visibility over the anomalous cloud-based activities was significantly increased, enabling the swift identification of the chain of suspicious activities involved in this compromise.

In this case, the prospective customer reached out to Darktrace directly through the Ask the Expert (ATE) service. Darktrace’s expert analyst team then conducted a timely and comprehensive investigation into the suspicious activity surrounding this SaaS compromise, and shared these findings with the customer’s security team.

Conclusion

Ultimately, this example of SaaS account compromise highlights Darktrace’s unique ability to learn an organization’s digital environment and recognize activity that is deemed to be unexpected, within a matter of days.

Due to the lack of obvious or known indicators of compromise (IoCs) associated with the malicious activity in this incident, this account hijack would likely have gone unnoticed by traditional security tools that rely on a rules and signatures-based approach to threat detection. However, Darktrace’s Self-Learning AI enables it to detect the subtle deviations in a device’s behavior that could be indicative of an ongoing compromise.

Despite being newly deployed on a prospective customer’s network, Darktrace DETECT was able to identify unusual login attempts from geographically improbable locations, suspicious email rule updates, password changes, as well as the subsequent mounting of a phishing campaign, all before the customer’s trial of Darktrace had even begun.

When enabled in autonomous response mode, Darktrace RESPOND would be able to take swift preventative action against such activity as soon as it is detected, effectively shutting down the compromise and mitigating any subsequent phishing attacks.

With the full deployment of Darktrace’s suite of products, including Darktrace/Apps and Darktrace/Email, customers can rest assured their critical data and systems are protected, even in the case of hybrid and multi-cloud environments.

Credit: Samuel Wee, Senior Analyst Consultant & Model Developer

Appendices

References

[1] https://www.gartner.com/en/newsroom/press-releases/2022-10-31-gartner-forecasts-worldwide-public-cloud-end-user-spending-to-reach-nearly-600-billion-in-2023

[2] https://www.upguard.com/blog/saas-security-risks

[3] https://www.microsoft.com/en-us/security/blog/2022/11/16/token-tactics-how-to-prevent-detect-and-respond-to-cloud-token-theft/

[4] https://learn.microsoft.com/en-us/powershell/module/exchange/disable-inboxrule?view=exchange-ps

[5] https://learn.microsoft.com/en-us/dotnet/api/microsoft.exchange.webservices.data.ruleactions.stopprocessingrules?view=exchange-ews-api

[6] https://learn.microsoft.com/en-us/dotnet/api/microsoft.exchange.webservices.data.ruleactions.movetofolder?view=exchange-ews-api

[7] https://blog.knowbe4.com/check-your-email-rules-for-maliciousness

Darktrace Model Detections

Darktrace DETECT and RESPOND Models Breached:

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Unusual Activity / Multiple Unusual External Sources for SaaS Credential

Antigena / SaaS / Antigena Unusual Activity Block (RESPOND Model)

SaaS / Compliance / New Email Rule

Antigena / SaaS / Antigena Significant Compliance Activity Block

SaaS / Compromise / Unusual Login and New Email Rule (Enhanced Monitoring Model)

Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)

SaaS / Compromise / SaaS Anomaly Following Anomalous Login (Enhanced Monitoring Model)

SaaS / Compromise / Unusual Login and Account Update

Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)

IoC – Type – Description & Confidence

hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/ - Domain – Probable Phishing Page (Now Defunct)

37.19.221[.]142 – IP Address – Unusual Login Source

35.174.4[.]92 – IP Address – Unusual Login Source

MITRE ATT&CK Mapping

Tactic - Techniques

INITIAL ACCESS, PRIVILEGE ESCALATION, DEFENSE EVASION, PERSISTENCE

T1078.004 – Cloud Accounts

DISCOVERY

T1538 – Cloud Service Dashboards

CREDENTIAL ACCESS

T1539 – Steal Web Session Cookie

RESOURCE DEVELOPMENT

T1586 – Compromise Accounts

PERSISTENCE

T1137.005 – Outlook Rules

Probability yardstick used to communicate the probability that statements or explanations given are correct.
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
Min Kim
Cyber Security Analyst

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July 24, 2026

Darktrace / EMAIL Expands Behavioral Defense Across Email and Collaboration Workflows

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Email and collaboration tools do more than carry messages. They are where organizations approve payments, share sensitive data, reset credentials, and make thousands of everyday decisions. Increasingly, they are interfaces through which humans direct AI agents in their daily activity. Email, Slack and Teams are high volume, rich with sensitive data, and an easy place to hide malicious activity.

The opportunity isn’t lost on bad actors. Darktrace / EMAIL detected more than 32 million high-confidence phishing emails globally in 2025, and 70% of those messages passed DMARC authentication.  Phishing is increasingly difficult to detect and familiar trust signals alone are not enough. People and security teams need to understand how a message fits the normal behavior of the sender, recipient, and organization. They also need to correlate activity across platforms to spot threats that span multiple channels.

To effectively secure against today’s evolved threats, security teams need to act at two levels: they need to help each employee make a safer decision ‘in the moment’, and they need to understand the wider patterns that may expose the business to risk.

Darktrace is introducing four new capabilities in Darktrace / EMAIL to address both challenges. The new features explain suspicious content more clearly to end users, strengthen the capabilities of Darktrace / Adaptive Human Defense with richer guidance, let organizations define their own patterns for detecting sensitive data in messages, and give security teams a process-level view of risk across email and collaboration workflows.

Darktrace / EMAIL Inbox Analysis highlights risky content within your emails

A warning is more useful when it explains what the user should look at. To help do that, we’ve expanded Darktrace / EMAIL’s Inbox Analysis Add-In to highlight potentially dangerous content within the body of emails that Darktrace / EMAIL flags as potentially suspicious or high risk.  

The add-in can highlight language designed to create urgency, financial references, requests for payment, suspicious links, and content that is unusual for the sender. Each highlighted element includes a pop up that explains why it may be suspicious. Instead of asking an employee to accept a verdict without context, the analysis helps them examine the message and make a more informed decision.

Enhanced Just-In-Time Training Banners in Darktrace / Adaptive Human Defense

Enhanced Just-In-Time Training Banners build on the same principle. The banners now include a contextual header, actionable advice, and specific detection context. This gives employees more useful guidance at the point of risk without adding unnecessary information or cognitive load.

Together, the capabilities help turn a warning into a short learning moment. Employees can see what looks unusual, understand what action to take, and build their judgment.

Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention

Sensitive data is different for every business. Standard categories such as payment card details or government identifiers matter, but organizations also have their own customer codes, project names, research formats, account structures, and internal identifiers.

Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention allows administrators to write custom expressions for the data their organization needs to protect. Matched content can trigger existing model actions and data loss prevention (DLP) workflows, extending Darktrace's DLP capabilities.

This extends data loss detection beyond a fixed library of common data types. Security teams can apply controls to information that is sensitive in the context of their own organization and adapt those controls as the business changes.

Introducing Email and Collaboration Workflow Risk Posture Dashboards

Some of the most important risks are not isolated events. They are repeated ways of working that create an opening for error, misuse, or attack. For example, a payment request may be one suspicious message, but a recurring approval workflow that relies on weak verification is a business process risk.

The new Email and Collaboration Workflow Risk Posture Dashboard analyzes email and collaboration data across Email, Microsoft Teams, Slack and Zoom to provide a process-level view of risk in the organization. These may include financial authorization workflows, sensitive data sharing patterns, and activity that could expose credentials.

The dashboard brings these patterns into a view and provides actionable recommendations. This helps security teams determine where to investigate or strengthen controls, where ownership needs to be clarified, and where the business may need to change a risky process. It gives CISOs a clearer view of how human and communication risk is embedded in everyday operations, not only where individual alerts occur.

Behavior connects the individual decision to the wider risk

These capabilities build on Darktrace’s unique behavioral approach to security. We use Adaptive AI to learn how people and AI normally behave within an organization, creating the context needed to recognize when activity changes.

Within the Darktrace Behavioral Defense Platform, Darktrace / EMAIL helps protect people against phishing, account takeover, data exfiltration, and human risk across email and collaboration tools. The new capabilities extend that protection in both directions. They give employees clearer context for the decision in front of them, while giving security leaders a broader view of the workflows and behavior that create risk across the organization.

The result is not simply more alerts. It is a better understanding of why something is risky, what action to take, and where the organization can reduce risk before a familiar process becomes an easy route for an attacker.

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Carlos Gray
Senior Product Marketing Manager, Email

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July 24, 2026

When Guardrails Break: Why Securing AI Requires Behavioral Detection and Autonomous Containment

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Bottom line up front: Governance, guardrails, identity controls, and secure development are necessary to secure AI, but they are not sufficient. AI systems are probabilistic, adaptive, and non-deterministic. Therefore, organizations need two additional layers of security:

  1. Behavioral-based detection that can identify when AI begins to act outside its intended purpose; and  
  2. Surgical, explainable autonomous containment that can stop risky activity before it causes material damage.  

That capability depends on multiple specialized AI models working together, not one LLM making every decision.

Organizations are embedding AI into development, business operations, and security workflows faster than most security programs can adapt. The risk is no longer limited to the model. It extends across prompts, data, identities, agents, memory, APIs, tools, permissions, and the trust relationships connecting them.

In my recent blog, Securing AI: Analysis of the Complete Security Stack with Governance and Controls, I outlined a defense-in-depth strategy spanning governance, identity, data security, secure development, runtime detection, autonomous containment, and recovery. The most urgent requirement across that architecture is the ability to understand how AI behaves in practice and contain it when that behavior becomes risky.  

Why non-deterministic systems require behavioral-based detection

Traditional controls remain foundational. Organizations need least privilege, strong identity controls, secure-by-design architecture, data governance, AI inventories, guardrails, testing, and clear boundaries on autonomy.

But deterministic controls, which assume predictable and repeatable behavior, cannot fully secure non-deterministic systems, where the same input may not always produce the same outcome.

AI agents can interpret the same instruction differently, chain individually authorized actions into an unsafe outcome, or pursue a legitimate goal through a method the organization did not anticipate. One of the most recent examples of this is the incident that OpenAI and Hugging Face jointly disclosed, where an autonomous agent escaped its intended testing boundaries and compromised Hugging Face infrastructure.  

An agent may have permission to access data and invoke a tool, but that does not mean every use of that access is appropriate. It is not enough to know whether an action is allowed. Organizations need to know whether it makes sense.

  • Is this normal for this agent?  
  • Is it acting within its intended purpose?  
  • Is it accessing unusual data, invoking an unexpected tool, or beginning to drift?  
  • Do a series of ordinary-looking actions become risky when viewed together?

Behavioral-based detection specific to an environment or organization with an understanding of context and risk enables provides the needed detection engineering for AI systems. It learns normal activity across people, systems, data, devices, and AI agents, then identifies deviations and evaluates their risk, intent, and context. This enables detection of misuse, abuse, compromise, manipulation, and unintended behavior even when no known attack signature or explicit policy violation exists.

Why accuracy is the foundation for SOC optimization

AI will only improve the SOC if it produces accurate, explainable, and actionable outcomes.

If analysts must manually validate every AI-generated finding because they cannot understand the evidence or confidence behind it, automation has not reduced workload. It has moved the workload. False positives increase fatigue. False negatives cause the most risk and damage to organizations. Inaccurate autonomous actions can disrupt critical operations.

Accuracy is therefore more than a model-performance metric. It is the prerequisite for analyst trust, SOC optimization, and safe autonomous response.

That accuracy is unlikely to come from one model.

Generative AI is valuable for natural-language analysis, summarization, and human interaction. But an LLM should not be the sole analytical engine for behavioral-based detection, investigation, risk assessment, and containment. Interpretability and consistency are required for high-consequence security decisions.

A stronger architecture uses multiple specialized AI systems collaboratively:  

  • Behavioral models can establish normal activity.  
  • Unsupervised learning can identify novel anomalies.  
  • Graph analysis can evaluate relationships among agents, identities, systems, and tools.  
  • Other models can correlate events, investigate competing hypotheses, and assess risk.  
  • Semantic models can analyze language where behavior-based language analysis is needed but this can be used in tandem with vector embeddings, graph neural networks, and a variety of other AI systems.

Each model contributes a different analytical perspective. Their outputs can corroborate one another, improving accuracy and creating a more reliable basis for response. The objective is not one model operating as an oracle. It is layered, adaptive intelligence designed to produce decisions the SOC can understand and trust.

Autonomous containment is required to secure autonomous systems

Many SOCs remain hesitant to trust LLM-based agents with autonomous containment. That concern is reasonable. A poorly selected response can isolate the wrong asset, stop a critical workflow, block a legitimate identity, or create more operational damage than the original incident.

But relying exclusively on human response is also not viable.

AI systems can operate at machine speed. They can expose sensitive data, execute workflows, modify records, call tools, or propagate actions across connected systems before an analyst can investigate and intervene. The behavior may be unintentional, the result of an agent optimizing toward a goal, or caused by misuse, compromise, prompt injection, or offensive AI.

Intent affects the investigation. It does not change the need to stop the damage.

Organizations need autonomous response, but it must be surgical and explainable. The objective is not to shut down an entire agent, user, application, or business process whenever an anomaly occurs. It is to interrupt the specific risky behavior: block an unusual connection, constrain a tool call, stop an abnormal data transfer, or temporarily limit an agent when it is performing anomalous, risky activity.  

That buys humans time. It stops the spread, limits damage, and allows the SOC to investigate without unnecessarily disrupting the business.

Layered, Adaptive AI provides a path forward

Darktrace has spent more than a decade researching and operationalizing layered, behavioral, Adaptive AI that learns a specific organization rather than relying only on historic attacks or predefined signatures.

The approach is designed to understand normal behavior, identify anomalous activity, assess its risk, correlate related events, autonomously investigate, and, when necessary, apply targeted containment while normal operations continue.

That sequence matters. Autonomous response cannot simply be added to the end of an LLM workflow. Trusted containment depends on broad visibility, continuous behavioral understanding, multiple analytical techniques, risk and context evaluation, autonomous investigation, explainability, and precise response actions.

This represents a more responsible model for security autonomy: not automation for its own sake, but controlled autonomy built to improve security outcomes and protect business operations.

Security must enable AI adoption

The answer for security teams is not to block AI. Organizations are adopting it to improve productivity, accelerate development, and create new business value.

But innovation without behavioral detection and autonomous containment is not sustainable.

Organizations should continue investing in governance, identity, least privilege, data security, secure MLOps, guardrails, testing, evaluation, validation, verification, kill switches, rollback, and forensic readiness. At the same time, they cannot wait for every governance program to mature before addressing runtime risk.

Behavioral-based detection and autonomous containment provide an immediate layer of resilience. They allow organizations to detect exploitation and risky AI behavior they did not anticipate, contain it at machine speed, and preserve human control over broader remediation.

The future of AI security will not be defined by a single model making every decision. It will be defined by multiple specialized AI systems working collaboratively, with sufficient accuracy, transparency, and context to support trusted autonomous action.

Surgical, explainable autonomous containment is no longer a future capability. It is a requirement for scaling AI securely today.

Learn how to build a defense-in-depth strategy for securing AI at scale in our talk at Black Hat on August 5 at 3:15 PM.  

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