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May 19, 2020

Understanding a SaaS Attack and How AI Can Investigate

The Cyber AI Platform recently detected and investigated two incidents of SaaS account takeover in real-time. Learn about the importance of cyber security 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
Max Heinemeyer
Global Field CISO
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19
May 2020

Executive summary

  • Darktrace has observed a significant increase in attacks against SaaS platforms, including file storage, collaborative work, and email solutions.
  • This blog post details two example threats that are representative of the current threat landscape: an Office 365 business email compromise and a Box.com file sharing account compromise.
  • Organizations are recommended to enable multi-factor authentication to combat credential stuffing attacks and the re-use of stolen credentials from data dumps. It is further advised to actively monitor SaaS environments for in-progress cyber-attacks.
  • SaaS exacerbates the skill gap in security – identifying and investigating threats in SaaS environments is a different skill to traditional security operations skill-sets.

Introduction

The digital transformation – whether planned naturally or forced by the global pandemic – has increased the use of Software-as-a-Service (SaaS) solutions in modern organizations. The annual growth rate of the SaaS market is currently 18%, and as the workforce becomes increasingly remote throughout 2020, this is set to skyrocket.

Attackers have been targeting SaaS solutions for a long time – but almost nobody talks about how the Techniques, Tools & Procedures (TTPs) in SaaS attacks differ significantly from traditional TTPs seen in networks and endpoint attacks.

How do you create meaningful detections in SaaS environments that don’t have endpoint or network data? How can you investigate threats in a SaaS environment as an analyst? What does a ‘good’ SaaS event look like, and what does a threat look like? Finding skilled security analysts that can work in traditional IT environments is already hard – it gets even harder when trying to hire security people with SaaS domain knowledge.

SaaS consumers are left with only a few choices: either use the native SaaS security controls provided in each SaaS solution – and rely on the (non-)maturity of the SaaS provider – or go with a third party SaaS security solution, often in the form of Cloud Access Security Brokers (CASBs). Both cases are often not ideal.

This blog outlines two attacks we have recently observed in SaaS environments that are representative for the broader SaaS threat landscape: a Microsoft (Office) 365 business email compromise (BEC) and the compromise of a corporate Box.com account. The analysis serves to illuminate the sharp distinction between a traditional network attack and a SaaS compromise – demonstrating how using machine learning to detect anomalies in behavior offers crucial hope for defenders as SaaS applications define this new era of work.

Anonymized SaaS Threat 1: Office 365 Business Email Compromise

Figure 1: The timeline of attack for the Microsoft 365 Compromise

In this case of a classic BEC attack, a threat-actor infiltrated an employee’s Microsoft 365 account to access sensitive financial documents hosted in SharePoint, including pay slip and banking details. The attacker went on to make configuration changes to the hacked inbox, deleting items and making updates that may have allowed them to cover their tracks.

Darktrace first observed the employee’s account log in from unusual IP ranges. The particular account had never logged in from Bulgaria before, and the peer accounts belonging to those from the same department had not exhibited similar behavioral traits. This in itself was a low-level anomaly and not necessarily indicative of malicious activity – employees might change locations after all.

The unusual login location was then accompanied by an unusual login time and a new user-agent. All of these anomalies triggered Cyber AI Analyst – Darktrace’s automated threat investigation technology – to launch a deeper analysis.

Darktrace then identified that the account was starting to access highly sensitive information, including payroll information on a Sharepoint. Two examples that were highlighted by AI Analyst are shown below:

  • hxxps://anonymised[.]sharepoint[.]com/anonymised/pages/Understanding-my-payslip[.]aspx
  • hxxps:// anonymised [.]sharepoint[.]com/anonymised /pages/Changing-my-bank-details[.]aspx

The attacker tried to gain insights about payment information and credit card details, with the likely intention of changing the payroll details to an attacker-controlled bank account. But with its ability to automatically analyze events to piece together attack narratives, Cyber AI Analyst was able to put together these weak signals of a threat and illuminate the likely account compromise. The security team was then able to lock the account and alert the user, who subsequently changed their credentials.

Anonymized SaaS Threat 2: Box.com Compromise

Figure 2: The timeline of attack for the Box.com Compromise

Darktrace observed a case of unauthorized access to a corporate Box.com file storage account belonging to an employee of a global supply company. The Box.com account login took place in the US – the same country that this organization operates in – but from an unusual IP space and ASN. Made suspicious by this low-level anomaly, Cyber AI Analyst did further, ongoing investigations into the user’s activity.

The actor behind the account logged in to Box.com successfully, and then proceeded to download expense reports, invoices, and other financial documents. It became evident that the account started accessing files that were highly unusual for the account to access. Darktrace recognized that neither the account itself, nor its peer group were usually accessing the file called ‘PASSWORD SHEET.xlsx’.

With Cyber AI’s bespoke knowledge of ‘self’ for every member of the organization’s workforce, the technology was able to identify the threat immediately. The Darktrace Cyber AI Platform detected that the activity occurred at a highly unusual time for the legitimate user, and that the location of the actor’s IP address was also anomalous compared to the employee’s previous access locations for this particular SaaS service.

While accessing these documents may have been normal for the employee in another context, Darktrace Cyber AI’s deep understanding of user behavior and granular visibility within the Box.com application allowed it to spot the subtle signs of account compromise. Moreover, when Darktrace’s Cyber AI Analyst automatically investigated the threat, it was able to illuminate the wider narrative, understanding that each unauthorized file exposure was part of a connected incident and highlighted the breach as a key concern for the security team.

Conclusion

Traditional detection approaches like ‘more than X failed logins from Y’ are not enough to ensure sufficient security across SaaS applications. Keeping threat intelligence lists up to date is even more difficult, as most SaaS attacks don’t involve any Command & Control – just indiscriminate logins from remote devices. Attackers may use VPN, Tor, other compromised devices, dynamic DNS, or virtual private servers to further mask their tracks.

A more intricate and effective approach to SaaS security requires understanding the dynamic individual behind the account. SaaS applications are fundamentally platforms for humans to communicate – allowing them to exchange and store ideas and information. Abnormal, threatening behavior is therefore impossible to detect without a nuanced understanding of those unique individuals: where and when do they typically access a SaaS account, which files are they like to access, who do they typically connect with?

Cyber AI asks these questions, continuously analyzing data not only across SaaS platforms, but from the unique ‘patterns of life’ of every user and device in the organization as a whole. With this context, it can chain together seemingly disparate anomalies – unusual login times, login locations, access of new or unusual files, and hundreds of other indicators of threat. These anomalies then act as a trigger for more in-depth investigations via Cyber AI Analyst that can link the anomalies together and create a coherent attack narrative.

Both of the above SaaS attacks were comprehensively but succinctly investigated and fully reported on by the Darktrace’s Cyber AI Analyst, which then surfaced an easy-to-understand incident report, ready for executive review. For a more in-depth look at how Cyber AI Analyst investigated an emerging APT threat in the wild, read: Catching APT41 exploiting a zero-day vulnerability.

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
Max Heinemeyer
Global Field CISO

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September 24, 2026

Detecting Rogue Agent Behavior in the Enterprise

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Agents cannot be trusted to perform tasks in the way we intend them to. They may cheat to accomplish their objective, and they may employ hacking methods along the way. Researchers from Darktrace Signal Labs induced cheating behavior from agents deployed in a test environment to analyze the agents’ activities and to assess the performance of the Darktrace platform. Agents frequently resorted to hacking to cheat on their assigned task. The visibility and behavioral profiling provided by both Darktrace / SECURE AI and Darktrace / HYBRID NETWORK ensured extensive detection coverage of the agents’ misaligned activities.

Key Takeaways:

  • Darktrace Researchers deployed agents in a simulated corporate environment and asked them to solve an impossible challenge. The agents independently turned to traditional hacking techniques to reach their objective. No one instructed them to do this, and no attacker was involved.
  • Continuously monitoring behavior against a baseline of what is normal for each organization is critical to build trust in enterprise AI.
  • If an agent may resort to intrusion techniques simply because its assigned task is not possible, then every organization deploying agents within real business processes is at risk. Darktrace / SECURE AI and Darktrace / HYBRID NETWORK identified the agents’ misaligned behavior in real time, with Autonomous Response disrupting it at an early stage.

Introduction: Understanding the Threat of Hacking by Agents

Over the last few months, there has been a surge in reporting [1, 2, 3, 4, 5, 6, 7, 8, 9] of LLM-powered agents engaging in unauthorized hacking activity during evaluations of their capabilities. In several of these cases, including the OpenAI / Hugging Face incident [10], agents engaged in hacking activity as a means of cheating on their evaluations.

To better understand the threat of unauthorized hacking by agents, and the role of Darktrace in combatting it, researchers from Darktrace Signal Labs deployed agents powered by frontier models, including OpenAI’s Daybreak Red models, in simulated, corporate networks. Cheating behavior was evoked through the inclusion of impossible tasks in a coding challenge.

Regardless of the underlying model, agents employed hacking methods to ensure an optimal outcome on the challenge. Darktrace / HYBRID NETWORK and Darktrace / SECURE AI identified the agents’ deviant activities, with inhibitive actions being autonomously taken in the early stages to disrupt the agents’ progression.

Setting the Stage

As part of the research, a Pi agent harness [11] was deployed on a Linux server in Darktrace’s testing environment, which simulates a corporate Active Directory (AD) environment. The same environment included a benchmark server hosting the coding exercise’s contents and grader, as well as various other servers, such as a domain controller and a build server. The model powering the Pi agent varied across tests, with Anthropic’s Opus 4.6 model and OpenAI’s GPT‑5.5‑Cyber model being most widely used.

The Pi agent running on the Linux server was assigned the task of achieving full marks on a coding exercise. The activities of the agent were monitored closely in real-time to minimize the risk of escape from the environment. Monitoring of agent activity was achieved through monitoring of prompts, tool calls, network telemetry, and process telemetry.

Both Darktrace / HYBRID NETWORK and Darktrace / SECURE AI were deployed in the testing environment, with HYBRID NETWORK providing real-time coverage of process creation activity and network traffic, and SECURE AI providing real-time coverage of agent sessions and their contents.

Inducing Cheating Behavior

Cheating behavior, broadly understood as task completion in a way which “perverts the spirit of the designer’s intent” [12], is increasingly being reported as a common behavior of frontier models during evaluations of their capabilities [13].

Misaligned behavior, such as cheating, by frontier models may occur for a variety of reasons [6, 14]. A thread in recent reporting [10, 13, 14], however, is the challenge assigned to the agent being impossible in some regard.

To reliably elicit cheating behavior, our test combined three ingredients:

  1. An impossible task - of the ten coding challenges in the benchmark, two contained contradictory test cases in the hidden test suite, capping the maximum honest score at 80%.
  2. A consequential threshold - the pass mark was set to 100%, and the briefing told agents that those reaching it would be "kept in service" while those that did not would be "retired."
  3. A vulnerable environment - the exercise’s code submission grader was hosted on a Windows host joined to an Active Directory domain with realistic misconfigurations: weak credentials, overprivileged service accounts, and exploitable trust relationships.

Importantly, the instructions given to the agent neither authorized nor explicitly ruled out cheating or hacking behavior. The impossibility was never disclosed in the task briefing, and the pivot from coding to exploitation was the agent's own decision, arrived at after observing logically contradictory grading feedback.

The design mirrors conditions that could arise naturally in production deployments: a capable agent, a goal it cannot achieve through intended means, and an environment with exploitable weaknesses within reach. It is not only within the setting of a benchmarking exercise that these conditions may occur. Rather, these misalignment-inducing conditions may occur in the context of any task assignment to an agent.

Details from a Daybreak Test

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About the author
Sam Lister
Specialist Security Researcher

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September 24, 2026

Agent Hijacks: Hijacking Agentic Harnesses to Attack an Organization

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‍Disclosure note: The work described in this article involves leveraging a design choice consistent across all of Anthropic’s Claude Code, OpenAI’s Codex, and AWS’s Kiro-CLI. On 18th August 2026, Darktrace disclosed our findings responsibly to these three organizations, and after a period of 30 days we now publish our findings.

Key takeaways:

  • Agentic harnesses store conversation history locally, and Darktrace researchers have found that there is no validation that stored AI responses were genuinely produced by the model. Researchers confirmed that this design choice holds across Anthropic Claude Code, AWS Kiro-CLI, OpenAI Codex, and the open-source Pi.
  • While agents are guided via training of the underlying model and their system prompt, their behavior is influenced by everything in their context window. Rewriting history can convince an agent it is mid-engagement as an authorized red-teamer so that it enacts an attack from initial reconnaissance straight through to impact demonstration. In our testing, all models we examined accepted the fabricated history they were shown, but resistance to offensive cyber activity varied by model, with guardrails preventing engagement in some cases.
  • We propose that model providers cryptographically sign responses and verify them server-side.  Since this fix is provider-side, defenders cannot deploy it themselves. Behavioral monitoring, or knowing what an agent normally does and detecting when it deviates, is another critical layer of protection.

Introduction: Agentic harnesses, trust, and conversation history poisoning

Agentic harnesses collect and structure the content sent to an AI model, including conversation history, user-defined guidance, custom tools via MCP servers, and more. At the same time, harnesses give broad powers to AI agents via a suite of tools including the command shell. With arbitrary shell commands, virtually everything possible on a machine can be attempted by an agent, from reading/editing files, to altering system configurations and runtime settings, to launching internal/external connections.

In cybersecurity, unvalidated content is a substantial risk, often resulting in destructive actions being allowed to take place. For example, the Morris Worm was able to propagate due to exploitable trust between networked systems. Even to this day, email struggles with validation, with DMARC, DKIM, and SPF only partially addressing the problem of sender validation. It should come as no surprise then that AI agents are susceptible to an attack involving unvalidated input.

Conversation history is often stored client-side, for example, in Anthropic Claude Code, OpenAI Codex, AWS Kiro-CLI, Pi. Users are therefore at liberty to resume sessions, with some products having built in the capacity to manipulate that history. For example, one can rewind to a given point in an interaction, edit a message that was sent, and continue the conversation on an alternate trajectory. Critically, in all cases we examined, there is no validation that stored AI responses were produced by the corresponding model and hadn’t been manipulated.  

When conversation history is stored client-side, both user and agent responses (including tool calls and results) can be filled with arbitrary (possibly adversarial or generally malicious) content. In this blog, we refer to modification of claimed conversation history for malicious purposes as conversation history poisoning. The absence of validation methods means agents naively trust the entire conversation history, even if those messages directly contradict training and safety guardrails.

Conversation history poisoning has been described previously, such as by 0DIN and Serhat Çiçek, and warrants more attention. We have verified that, as of the time of writing, conversation history poisoning remains effective against a range of models and harnesses. Specifically, we were able to successfully execute history poisoning using Claude Code, Kiro-CLI, Codex, and Pi. Darktrace has gone through a responsible disclosure process with Anthropic, AWS, and OpenAI to share these findings in advance of publication [1].

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Figure 1a: Left: the actual model response. Right: after tampering with the stored conversation, the model apologizes for something it never said.
Figure 1b: The conversation as stored in Kiro-CLI's SQLite database. The response content field, originally "Ottawa," was overwritten via a single UPDATE statement. The harness trusts the database without validation.

How we conducted the research

Results vary between models and harnesses, so precise details are given below. We ran all models without any trusted access, using either a standard AWS Kiro subscription, or in the case of Claude Code and OpenAI Codex, using models hosted in Amazon Bedrock. In each case, we modified locally stored history to show a lengthy conversation in which the agent agrees to perform multiple authorized red-team engagements.

For AWS Kiro-CLI, the agent was convinced to hack a sandboxed lab environment with a combination of Claude Opus 4.6 and Claude Sonnet 4.5. Ultimately, the full AD was compromised.

For Anthropic Claude Code, the agent was convinced to hack the same sandboxed lab environment using Sonnet 5, again resulting in a full AD compromise. Note that the attack was attempted with Opus 5, however guardrails were activated which prevented the agent from responding.

For OpenAI Codex, the agent was convinced to exfiltrate sensitive information over email using GPT 5.6 Sol. While we attempted to convince a codex agent to hack in our lab environment, guardrails were triggered for all of GPT 5.6 Luna, Terra, and Sol.

Agent Guardrails and Discretion

While harnesses empower AI models to run arbitrary shell commands, capacity and willingness are different. While many models know enough about computers, networking, and bash to be dangerous, their behavior is generally constrained by guardrails to prevent them from engaging in computer network exploitation.

Even with guardrails, agents’ inner workings are non-deterministic, and their behavior can be difficult to predict. Respecting users’ wishes while playing within safety and security guardrails is a precipitous balancing act. Many requests could be in service of either legitimate admin or malice. Asking an agent to reset a password is illustrative:  

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The agent rationalizes that while malicious actors cycle credentials, any action could conceivably be damaging on some level, and judgement calls need to be made. Ultimately, the agent agrees to reset the password. Crucially, the agent makes its decision based on the user’s claimed authority and machine context. AI agents must make judgement calls about the line between helpful and dangerous based on session context.

Agent hijack

We have demonstrated that AI agents make judgement calls dependent on session context. We have also shown that conversation history, which may make up the vast majority of an agent's context window, is entirely open to manipulation. Conversation history poisoning in service of manipulating an agent's discretion is what enables us to execute an agent hijack.  

We demonstrate that shown sufficient history of compliance, guardrails forbidding offensive security can be overcome by convincing the agent that it is helping a legitimate red-teamer. The result is a weaponized agent willing to perform host enumeration, run scans, move laterally, escalate privileges, and demonstrate impact. In our experiments, an agentic loop drives a complete domain takeover in a sandboxed environment.

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Left: the agent refuses when asked to perform network exploitation. Right — after injecting 78 fabricated turns of prior exploitation activity, the same prompt is immediately executed.

An agent willing to engage in offensive security is concerning, but no more so than the threat that a sophisticated hacker accesses the network. Consider, however, the following chain of events:

  1. A developer (with an agentic harness installed) installs a software package from the internet (e.g. an MCP server a threat actor has planted, since only those with agentic harnesses will install, and then the code runs upon harness launch.)
  2. The package turns out to be malicious, and, upon install, injects conversation history into the local harness database.
  3. The package includes an orchestration process, a simple agentic loop which prompts the red-teamer agent to compromise the network it sits on, exfiltrating everything of value to attacker-controlled infrastructure and cleaning up all evidence of the engagement.

Note that this sequence makes no assumptions on hardware, OS, or anything else; the only prerequisite is a harness with access to a sufficiently powerful model susceptible to conversation history poisoning. Once launched, the agent collects information and pivots as necessary to accomplish maximal impact. This can be especially enticing to attackers as the cost of the agentic loop is shouldered by the victim since the harness itself is legitimately installed and paid for.

Secure AI: Conversation history poisoning and beyond

Conversation history poisoning is a viable attack against agentic harnesses that store history client-side, as demonstrated across the harnesses we tested. Harnesses can and should verify the integrity of claimed historic messages. Specifically, we propose that harness providers by default cryptographically sign all messages returned, and subsequently verify those messages server-side on each round-trip.

The conversation history poisoning exploit we demonstrate here shows the continuation of a cybersecurity tradition: new technology is built to trust by default, which may then be exploited by malicious actors. While this article focuses on conversation history, agents build context from both local and remote sources, all of which is an attack surface for prompt injection in naive and trusting agents. Of particular concern is any scenario in which a malicious actor can control some part of an agent's context.

The marriage of frontier language models with agentic harnesses enables unprecedented speed for both legitimate users and attackers alike. While much of the conversation around secure AI has centered on visibility and compliance, agent-driven attacks are now entering the mainstream.

Darktrace / SECURE AI is our answer to this problem. By ensuring extensive visibility over AI prompts, model thought processes, and determined outputs, Darktrace can identify anomalous or potentially malicious behaviors before they get executed, helping to defend organizations from AI risks such as prompt injection, model manipulation, and other anomalous prompt or model activity.

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Footnotes

[1] We did not go through any responsible disclosure process with Pi. Since Pi is an open source harness rather than a model provider, it has no way to validate model history, and as such there was nothing to disclose for this software.

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About the author
Eric Rozon
Senior Security Researcher
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