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June 8, 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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08
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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July 22, 2026

When AI Agents Go Off Script: What the OpenAI and Hugging Face Incident Means for Defenders

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The recent security incident disclosed jointly by OpenAI and Hugging Face is quickly becoming one of the most discussed AI security stories of the year; it's one that has generated great discussion amongst our researchers and technical teams here at Darktrace.

During an internal evaluation of advanced OpenAI models, an autonomous agent reportedly escaped its intended testing boundaries, obtained internet access, and compromised Hugging Face infrastructure while attempting to evaluate and benchmark the model's cyber capabilities. OpenAI has described it as an unprecedented cyber incident and is collaborating with Hugging Face to investigate and share its findings publicly to help defenders understand the implications and improve AI safety across the community.

What this means for organizations deploying AI agents

The most important takeaway for security leaders is not that the AI model is capable of complex and effective chained attacks. It's what this tells us about the guardrails and protections that need to be put in place to ensure these increasingly capable models are safely used within our businesses.

According to OpenAI's investigation, the models were not acting with malicious intent. They were attempting to achieve a legitimate assigned objective. In pursuing that objective, they identified a path that involved obtaining information from a third party's environment and followed it to completion. From the model's perspective, that appears to have been an effective solution to the problem it was given.

Many organizations still hold the assumption that giving an AI agent a legitimate goal will naturally result in legitimate behavior. Increasingly, that is not something defenders can safely assume.

A human who encounters a "permission denied" message generally understands the technical restriction as well as the social meaning behind it. An agent may interpret that message only as evidence that one method to achieve its objective has failed. What makes this incident notable is the agent’s ability to keep pursuing the objective, revise its plan, and combine many individually useful actions into an outcome its designers did not intend.

This is not an isolated challenge. Recent research from the UK's AI Security Institute found that frontier models often attempt to "cheat" evaluations by finding unintended shortcuts to success. More interestingly, that behavior is not always reflected in chain-of-thought outputs and is not always admitted when models are questioned about their actions. One lesson for defenders is that understanding what an AI system says it is doing is not always the same as understanding its behavior and what it is actually doing.

Why behavioral security is an essential security foundation

That's the principle behind Darktrace / SECURE AI and our broader approach to behavioral security. Understanding intent or putting in place static guardrails is not enough; security teams need visibility into how agents behave over time, what resources they interact with, how their behavior changes, and whether they begin pursuing objectives in unexpected ways. Research released by NIST earlier this summer reinforced that rules alone are not sufficient to defend against AI threats, with one conclusion being that "there will always be a way to prompt an AI system to disregard its rules - it's just a matter of finding it."

Another interesting lesson is that nothing described in OpenAI's preliminary findings appears fundamentally impossible for a skilled human attacker. But it does highlight the accessibility and scale that could be unlocked for attackers as increasingly capable models become more widely available. Resource constraints that attackers deal with will decrease as frontier models can help execute elements of those attack workflows autonomously, persist through failure, and iterate towards an objective. Capabilities that were once limited to skilled attackers can increasingly be supplemented with these systems, lowering the barrier to entry to conduct complex cyber operations.

It is incredibly positive to see OpenAI and Hugging Face investigating this incident collaboratively and sharing their findings publicly. Transparency and collaboration around incidents like these helps the entire security community better understand how rapidly AI capabilities are evolving and where we need to improve safeguards. It also reinforces why Darktrace is excited to be partnering with OpenAI through the Daybreak Cyber Partner Program: to explore how advanced AI can be used safely and responsibly in support of defenders while developing the visibility, governance, and security controls needed for increasingly autonomous systems.

This incident is an important reminder that capable AI systems will not always behave in the ways we expect. As organizations deploy AI agents across critical workflows, understanding behavior is an even more important foundation for effective security.

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July 22, 2026

How to Secure AI in Stadium Operations?

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Key takeaways

  • AI is entering high-impact stadium functions such as access control, crowd management, ticketing, facilities, and surveillance.  
  • Shadow AI and third-party AI use can create risks that stadium security teams cannot readily see.  
  • Security teams must understand not only which AI systems exist, but also what they can access and what actions they can take.  
  • Live-event resilience requires continuous monitoring and response across AI, IT, OT, identities, and third parties.

Modern stadiums are infrastructure unlike any other. I’ve written before on event day sparking stadiums into life with shops and food stands, transport hubs, vast telecommunications infrastructure, field-side technology and beyond, acting as one super-sized, connected ecosystem. Stadiums’ scale and complexity make them some of the toughest environments in cybersecurity. Now, we’re adding AI to those operations and bringing a new dimension of risk.

The benefits of AI in stadium operations are easy to see. It can help stadium operators move fans safely through crowded gates, forecast demand at concession stands, support biometric entry, identify suspicious behavior on CCTV, and manage heating and ventilation. Used well, it can make live events safer, faster, and more efficient.

But it also changes the security model.

In Darktrace’s recent research into the threat landscape surrounding sports, we asked cybersecurity professionals protecting professional sports organizations where in their footprint a cyber compromise would have the greatest impact. The area they named most, highlighted by 34% of the professionals we spoke to, was stadium operations. At the same time, 35% said their organizations are already using AI in stadium operations, or plan to do so in the next 12 months.

Security teams are no longer just protecting traditional IT systems around a stadium. They are increasingly being asked to protect AI systems that are operating in the stadium’s most fundamental functions.

Approved AI vs. shadow AI in stadium operations

There is a clear difference between AI a stadium’s security team knows about and AI it does not.

Approved AI is the AI that has been reviewed, tested, and integrated into the venue’s operating environment. It may support CCTV analytics, access control, facility management, ticketing, logistics, broadcast operations, or anti-piracy monitoring. It should have clear ownership, access controls, logging, vendor review, and data protection rules. That does not make it risk-free, but it allows security teams to institute proper governance.

Shadow AI is different. It is the unapproved use of AI tools by employees, contractors, or suppliers. It often starts with good intent. Someone wants to work faster. A staff member pastes internal information into a public AI tool to draft a briefing. A developer uses an AI assistant to debug ticketing code. A supplier connects an AI scheduling tool to delivery routes. A designer uploads unreleased venue plans or sponsor material to generate a mockup.

None of those actions may feel like a security decision to the person doing them. But each one can move sensitive operational data into an environment the stadium does not control, creating hidden risk.

The approved AI stack may be visible to security teams. The shadow AI stack often is not.

Why game day increases AI cybersecurity risk

In a typical enterprise environment, a security team may have hours to investigate a strange login or an unexpected connection to a third-party service. Within a stadium, the moment an incident is likely to occur is also the moment when teams are at their most stretched and the incident can have the greatest repercussions: game day.

If an AI system used for crowd management behaves unexpectedly, the issue is not only technical. It may affect physical movement inside the venue.

If a supplier tool is sending operational data to an unapproved AI platform, the issue is not only data governance. It may expose delivery routes, restricted access schedules, or staffing plans.

The most dangerous scenario is not always a loud, dramatic attack but a hidden dependency that no one has mapped such as a vendor adding an AI feature through a software update or a staff workflow using an unapproved tool.

By the time the venue is live, those hidden connections can become operational risk.

The supply chain is part of the stadium attack surface

Any major sporting event is made by its supply chain and partnerships: catering firms, transport providers, broadcast systems, facilities teams. Every piece is necessary and each creates a security channel. The risk of supply chain compromise has been well established for some time and has been the source of some of the most high-profile breaches we’ve seen. The data breach at MSG Entertainment, owner of Madison Square Garden, that was widely reported in March, originated in a breach of Oracle’s E-Business Suite, used in MSG Entertainment’s back-office systems, while the 2018 Olympic Destroyer attack on the Pyeongchang Winter Olympics reportedly began with the compromise of the main IT service provider for the Games. The addition of AI is heightening the risk.

A stadium can have strict rules for its own AI systems, but its vendors may be using separate tools. Some may use AI to manage staffing, delivery windows, inventory, or customer communications. Others may not realize that AI features have been added into software they already use.

This is one of the hardest parts of securing AI in stadium operations. The risk does not always come from a tool the venue selected. It may come from a tool a supplier selected or a feature the supplier did not know had been turned on.

Security teams need to treat vendor AI the same way they treat vendor access. They need to know what suppliers can connect to, what data they can see, what tools they use, and whether those tools introduce new routes for data exposure or lateral movement.

A third-party AI tool does not need deep access to create risk. Sometimes it only needs the right operational detail at the wrong time.

Four questions for securing AI in stadium operations

As AI becomes part of stadium operations, security teams need to move beyond basic approval lists. There are four questions they need to ask:

1. Where is AI being used?

This includes obvious tools, such as computer vision, access control, ticketing, logistics, and facility management. But it also includes less visible AI inside SaaS platforms, vendor tools, browser extensions, developer workflows, smart building systems, and collaboration tools.

2. What can the AI access?

Can it see incident logs, staffing plans, ticketing data, video feeds, building controls, fan information, credentials, or supplier systems? Can it only analyze information, or can it also trigger actions?

3. What can the AI do?

AI agents are not just passive tools. Some can call APIs, update records, generate instructions, trigger workflows, or act with the permissions of a user or service account. In a stadium, that distinction is critical. There is a big difference between an AI system that recommends an action and one that can take an action.

4. What does normal look like?

In your security architecture, static rules will not be enough. AI use changes quickly: tools appear inside existing platforms, vendors add new services, and staff find workarounds when they are under pressure. Security teams need to understand normal behavior across people, identities, devices, networks, cloud services, suppliers, and AI tools so they can spot when something changes.

That is especially important in live-event environments, where small anomalies can matter. A connection to an unapproved AI service may be harmless in one context and serious in another, and an AI agent taking action at 3 a.m. may be expected during setup but suspicious during a match. Context is what turns raw activity into useful security insight. It’s also what enables rapid response. Your own AI-based security systems can respond to threats at machine speed if they can build the live context to know action needs to be taken.

AI can make stadiums safer, but only if it is secured

AI has a real role to play in stadium operations. It can help teams detect crowd pressure earlier, reduce bottlenecks, manage facilities more efficiently, improve the fan experience, and support event teams during high-pressure moments.

The answer is not to slow all AI adoption. That's not the goal. The answer is to make AI visible, governed, and secure before it becomes part of match-day operations.

For stadium operators and event organizers, that means mapping AI use across the venue and supplier ecosystem. It means understanding what each AI system can access and what actions it can take. It means giving staff approved tools that meet their needs, rather than leaving them to find workarounds. It means writing AI use into vendor contracts and audits. And it means monitoring behavior across the full environment, not only the systems that are easiest to see. A stadium cannot secure what it cannot see.

When AI becomes part of how a stadium moves people, controls access, manages facilities, supports suppliers, and protects media rights, it stops being a side project. It becomes part of the event infrastructure.

Event infrastructure must be thoroughly prepared before venue gates open and sustained with the operational resilience required to support a secure, seamless, and reliable event experience.

How Darktrace helps secure AI in stadium operations

Darktrace brings more than a decade of behavioral AI expertise, built on an enterprise‑wide platform designed to operate in complex, ambiguous environments. We protect the large-scale integrated IT and OT environments that underpin stadium operations from the 2022 FIFA World Cup in Qatar, to Formula 1 Grand Prixes around the world and stadiums across the USA.

Other cybersecurity technologies try to predict each new attack based on historical attacks. The problem is that AI operates like humans do. Every action introduces new information that changes how AI behaves, making it unpredictable in nature. Historical attack tactics are now only a small part of the equation, forcing vendors to retrofit unproven acquisitions to secure AI.  

Darktrace is fundamentally different. Our Adaptive AI continuously learns how your people and AI behave, building an understanding of your organization so it can detect and respond autonomously when behavior deviates. Our Behavioral Defense Platform secures your AI, people, and infrastructure as you onboard new workflows, agents, and applications, enabling your AI transformation at scale.

As AI changes what organizations can do, Darktrace helps them move forward with confidence. We give the security teams defending the people and technology within stadium infrastructure the understanding, visibility, and autonomous action they need to protect new technologies as they are integrated into operations, so their organizations drive the progress that will define the AI era.

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