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January 28, 2025

Bytesize Security: Insider Threats in Google Workspace

Insider threats pose significant risks due to access to internal systems. Darktrace detected a former employee attempting to steal data from the customer’s Google Workspace platform. Learn about this threat here.
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
Vivek Rajan
Cyber Analyst
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28
Jan 2025

What is an insider threat?

An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.

Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.

For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.

Attack overview: Insider threat

In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.

While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.

A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.

Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.

In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.

Conclusion

Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.

Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.

Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Get the latest insights on emerging cyber threats

Attackers are adapting, are you ready? This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.

  • Identity-based attacks: How attackers are bypassing traditional defenses
  • Zero-day exploitation: The rise of previously unknown vulnerabilities
  • AI-driven threats: How adversaries are leveraging AI to outmaneuver security controls

Stay ahead of evolving threats with expert analysis from Darktrace. Download the report here.

Appendices

Darktrace Model Detections

SaaS / Resource::Unusual Download Of Externally Shared Google Workspace File

References

[1]https://www.adobe.com/creativecloud/file-types/image/vector/indd-file.html

MITRE ATT&CK Mapping

Technqiue – Tactic – ID

Data from Cloud Storage Object – COLLECTION -T1530

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
Vivek Rajan
Cyber Analyst

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June 24, 2026

A New Security Challenge: The Curious Case of Prompt Language Analysis

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Why prompt analysis is emerging as a key AI security challenge

If securing AI has been one of the defining cybersecurity conversations of the past year, prompt analysis is quickly becoming one of its most interesting frontiers.

Security leaders are under pressure to understand how AI is being used across the business. In some organizations, that means governing employee use of chatbots. In others, it means overseeing copilots embedded into SaaS platforms, monitoring coding assistants, or assessing the growing footprint of autonomous agents. However different these use cases may appear on the surface, they share a common factor: humans and machines are usually interacting with enterprise systems through language.  

How prompt language differs from traditional security telemetry

For years, defenders have become used to working with familiar forms of telemetry: email traffic, network connections, API calls, endpoint processes, authentication events. Prompt language is different. It is not simply another log source. It is an expression of intent, instruction, curiosity, urgency, and sometimes manipulation. It reflects the end-goal of a user or agent, but not always with enough surrounding context to interpret the risk correctly.

Why existing security approaches only partially explain prompt risk

A growing number of vendors are approaching the task of securing AI from the angle they know best. Perimeter vendors are extending web or browser controls into AI usage. Identity vendors are emphasizing agent permissions and access governance. Data security and DLP providers are focusing on content inspection and exfiltration risk. All of these perspectives matter, but individually can’t fully explain the problem.

The challenge with securing AI is not just that a new application category has emerged. It is that language has become a new operating layer in the enterprise.

Employees now use prompts to summarize documents, generate code, analyze spreadsheets, query internal knowledge, and trigger multi-step actions through agents. In each case, prompt language acts as the interface between human intent and machine execution. That makes prompts incredibly valuable from a security perspective., as they can hint at misuse, policy violations, data exposure, or attempts to circumvent controls. However, they can also be deeply ambiguous when viewed in isolation.That ambiguity is the heart of the issue.

Prompts as behavioral signals, not just text to classify

A prompt by itself tells you what was asked. It does not necessarily tell you whether the request is expected, risky, accidental, or entirely legitimate in context. Two nearly identical prompts can carry very different meanings depending on the role and function of who issued them, , what systems they can access, and what actions followed. In other words, prompts are not just text to classify. They are behavioral signals to interpret.

Example: How context changes prompt risk entirely

Consider a common enterprise scenario. An employee is pulled into a new project with an aggressive deadline. Almost overnight, their use of AI tools spikes. They begin prompting more frequently, working across unfamiliar documents, querying new data sources, and interacting with more systems than usual to accelerate delivery. Viewed narrowly, this may look suspicious. Prompt volume increases, file access patterns change, API and SaaS activity rise. From some vantage points, it may resemble insider risk or unmanaged AI usage.

But now add context. Imagine that, earlier that day, the employee received instructions from a senior leader asking them to support a time-sensitive initiative. Their communication history shows that this leader is a legitimate reporting-line superior. Their recent collaboration patterns align with the new project team. Their subsequent activity, while unusual for that individual’s baseline, is consistent with the business task they were assigned.

What initially looked like a risk event may actually be a normal response to business pressure. Without the surrounding context of communication, organizational relationships, and broader behavioral patterns, prompt activity alone could generate more noise than insight.

The reverse is also true. A prompt may appear benign on the surface while the context around it suggests elevated risk. A request that seems routine could originate from a compromised user, a newly connected external agent, a shadow AI workflow, or a user acting outside their normal role. The language itself may not contain anything obviously malicious, but the surrounding conditions may tell a very different story.

What security teams need to analyze prompts effectively

The future of prompt analysis is not just about understanding language. It is about understanding language in context.

To do that well, security teams need more than prompt inspection. They need to understand:

  • Who is issuing the prompt, whether human or agent
  • How that identity normally behaves across the enterprise
  • What systems, data, and workflows are connected to the interaction
  • Which relationships and communications explain the surrounding activity
  • Whether the downstream actions align with expected business behavior

When those layers are absent, prompt analysis can become another isolated control surface: useful in theory, but limited in practice. Security teams may detect unusual wording but miss the operational function behind it, overreact to benign changes in behavior, or miss subtle misuse because the prompt itself did not appear dangerous.

How organizations should think about prompt analysis going forward

Security teams have seen this pattern before. In the cloud, posture without runtime context left important gaps. In identity, access control without behavioral understanding missed misuse that looked legitimate on paper. In data security, content inspection without business context often created friction without resolving risk. AI is exposing the same lesson again: controls are strongest when they are coordinated, not isolated. As organizations work to secure AI and identify gaps across their security operations, prompt analysis will become an increasingly important source of insight, but only as part of a broader strategy.

Prompt analysis will undoubtedly become more common, as prompts are one of the clearest windows into how people and agents are using AI systems. However, what matters most is not simply collecting prompts or filtering dangerous phrases, but being able to place that language inside a wider behavioral and operational picture.

Figure: Darktrace / SECURE AI reconstructs the full sequence of events, showing every user and agent interaction in context, with risky prompts clearly highlighted and labelled - PII, Sensitive Data, and more.​

At Darktrace, this is the key lesson emerging from the market: prompt language does matter, but it does not stand alone. It is most valuable when treated as a new behavioral input that can enrich understanding across the enterprise, not as a self-contained source of truth.

Why prompts become less useful when analyzed in isolation

The curious case of prompt language analysis, then, is this: the more important prompts become, the less useful they are in a vacuum.

The real opportunity is not just to see what was asked. It is to understand why it was asked, what it meant in that moment, and what happened next.

For a deeper look at how organizations are approaching this challenge from the strengths of prompt analysis to its limitations in isolation see Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches, which expands on the role prompt-level controls play within a broader, context-driven security strategy.

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About the author
Nabil Zoldjalali
VP, Field CISO

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June 23, 2026

Advancing the Use of Frontier AI in Cybersecurity: Darktrace Joins the OpenAI Daybreak Cyber Partner Program to Explore Defensive AI Integrations

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Darktrace joins the OpenAI Daybreak Cyber Partner Program

Today, we announced that Darktrace is joining the OpenAI Daybreak Cyber Partner Program. We’ll be partnering with OpenAI to explore how their cyber capabilities can be integrated within Darktrace products and services to bring new capabilities to our customers.

This partnership is an exciting opportunity to bring together Darktrace’s behavioral AI modelling of the organization with OpenAI’s advanced contextual capabilities to create a new level of understanding for security teams. To understand the impact, it’s helpful to start with how we think about the problem.  

At Darktrace, we built our AI in support of the core belief that cybersecurity needs to understand the business it is defending. That's why our Self-Learning AI is designed to help organizations understand normal and abnormal behavior for each organization across their digital environment, including users and identities, networks and cloud, email and collaboration tools, and now AI systems and agents with the rollout of Darktrace / SECURE AI™.  

Our goal was never simply to spot known attacks faster. It was to help defenders understand how their organization behaves, potential risks and impact, and where disruption could take hold so they could prepare for the unknown threats that they may not have seen or even imagined before.  

That’s exactly what is happening across the threat landscape today. Attacks keep changing; techniques shift, infrastructure evolves, and attackers move with more speed, precision, and context. And now they have even more AI and automation on their side. Attackers are exploiting identities, trusted services, SaaS applications, and business workflows. They are not always breaking in; often, the threat may come from within the organization in the form of insider threat or even rogue agents.  

In this reality, defenders need a combination of deep AI modelling of the organization and AI that can connect identified threats to concrete business context, translating this information into real world value, and allow action before risk becomes disruption.

That is the opportunity we see in partnering with OpenAI.  

What is the OpenAI Daybreak Cyber Partner Program and why is Darktrace joining

The OpenAI Daybreak Cyber Partner Program is focused on advancing the safe use of AI for cybersecurity. As part of the program’s next phase, OpenAI is working with a select group of trusted partners including Darktrace on scoped product integrations, managed services, and partner-delivered defensive capabilities. We’ll be exploring how OpenAI’s advanced frontier AI capabilities can support defenders in the tools and workflows they already use each day.

For Darktrace, this is a natural extension of our expertise and the work we have been doing for a decade: safely and securely applying the most effective AI techniques in combination to understand organizations, detecting malicious activity at the earliest indicators, and helping cyber defenders act faster.  

By using the advanced models and more precise safeguards available in the OpenAI Daybreak Cyber Partner Program, Darktrace and OpenAI will combine Darktrace’s real-time behavioral understanding of an organization's digital estate with OpenAI's ability to interpret wider business context.  

This is a unique and powerful combination of insights that could give organizations deeper context on technical risk and help them prioritize workloads and investigations based on potential impact to revenue, operations, and resilience. It can also provide security teams and executives with intelligence into which events matter most to the business, why they matter, and what action to take. Not just finding, for instance, that an agent is compromised, but highlighting that the compromised agent could shut down order fulfilment within the next three hours.  

Why the Darktrace and OpenAI partnership matters for defenders

Security teams today have more attack surface, more complex environments to protect, and an increasing volume of threats. The ability to act quickly is critical, but they also need to be able to focus on the risks that could have the greatest business impact.

That is especially important as attackers use AI to scale phishing, automate reconnaissance, find weaknesses, and blend into normal business activity. At the same time, organizations and their employees are using AI to innovate, which introduces an even broader attack surface and new set of risks. Defenders need AI that can operate across the same complexity, but safely, transparently, and in service of building more resilience. And they need a way to safely adopt, govern, and defend AI across their organizations.

Joining the OpenAI Daybreak Cyber Partner Program is another step in that direction. We are still early in this work, and we will take a careful, disciplined approach. But the direction is clear: protecting organizations requires AI that understands the business, not just the attack.

At Darktrace, that is exactly where we remain focused and why we are so excited about this partnership with OpenAI.  

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