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May 25, 2022

Multi-Account Compromise in Office 365

Learn how internal phishing can compromise accounts swiftly & how Darktrace/Apps can prevent future attacks effectively.
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
Laura Leyland
Cyber Analyst
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25
May 2022

In February 2022, Darktrace detected the compromise of three SaaS accounts within a customer’s Office 365 environment. This incident provides an effective use case for highlighting how Darktrace/Apps and Darktrace/Email can work together to alert to unusual logins, app permission changes, new email rules and outbound spam. It also emphasizes an instance where Darktrace RESPOND/Apps could have been set to autonomous mode and stopped additional compromise.

Account Compromise Timeline

February 9 2022

Account A was logged into from a rare IP from Nigeria with the BAV2ROPC user agent which is commonly associated with SaaS account attacks. BAV2ROPC stands for ‘Basic Authentication Version 2 Resource Owner Password Credential’ and is commonly used by old email apps such as iOS Mail. It is often seen in SaaS/email account compromises where accounts have ‘legacy authentication’ enabled. This is because, even if multi-factor authentication (MFA) is activated, legacy protocols like IMAP/POP3 are not configured for MFA and so do not result in an MFA notification being sent.[1][2]

Account A then created a new email rule which was named as a single full stop. Attackers commonly create new email rules to give themselves persistent access by using the ability to forward certain emails to external email accounts they own. This means that even if the account’s password is changed or MFA is turned on, the attacker keeps getting the forwarded emails as long as the rule remains in place. In this case, the attacker configured the new email rule using the following fields and features:

  • AlwaysDeleteOutlookRulesBlob – hides any warning messages when using Outlook on the web or Powershell to edit inbox rules. It is likely that the attacker had a set list of commands to run and didn’t want to be slowed down in the exploitation of the account by having to click confirmation messages.
  • Force – hides warning or confirmation messages.
  • MoveToFolder – moves emails to a folder. This is often used to move bounced emails away from the inbox in order to hide the fact the account is being used to send emails by the attacker.
  • Name – specifies the name of the rule, in this case a single full stop.
  • SubjectOrBodyContainsWords – emails with key words are actioned.
  • StopProcessingRules – determines whether subsequent rules are processed if the conditions of this rule are met. It is likely in this case the attacker set this to false so that any subsequent rules would still be processed to avoid raising suspicion.

Account A was then observed giving permission to the email management app Spike. This was likely to allow the rapid automated exploitation of the compromised account. Attackers want to speed up this process to reduce the time between account compromise and malicious use of the account, thus reducing the time security teams have to respond.

Figure 1: Screenshot from SaaS console showing the timeline of giving consent to the email management application Spike and the creation of the new inbox rule

The account was then observed sending 794 emails over a 15 minute period to both internal and external recipients. These emails shared similar qualities including the same subject line and related phishing links. This mass spam was likely due to the attacker wanting to compromise as many accounts and credentials as possible within the shortest timeframe. The domain of the link sent in the emails was spikenow[.]com and was hidden by the text ‘View Shared Link’. This suggests that the attacker used Spike to send the emails and host the phishing link.

Figure 2: Screenshot of AGE UI showing the spike in outbound messages from the compromised account – the messages all appear to be the same format
Figure 3: Screenshot from Darktrace/Email of the link and text that masked the link: ‘View Shared File’

Within 15 minutes of this large volume of outbound email from Account A, Account B was accessed from the same rare IP located in Nigeria. Account B also created a new email rule which was named a single full stop. In addition to the previous rules, the following rules were observed:

  • From – specifies that emails from certain addresses will be processed by the rule.
  • MarkAsRead – specifies that emails are to be marked as read.

Due to the short timeframe between the phishing emails and the anomalous behavior from Account B, it is possible that Account B was an initial phishing victim.

Figure 4: Screenshot of the SaaS console showing Account B login failures, then successful login and inbox rule creation from the rare Nigerian IP

February 10 2022

The next day, a third account (Account C) was also accessed from the same rare IP. This occurred on two occasions, once with the user agent Mozilla/5.0 and once with BAV2ROPC. After the login at 13:08 with BAV2ROPC, the account gave the same permission as Account A to the email management app Spike. It then created what appears to be the same email rule, named a single full stop. As with Account B, it is possible that this account was compromised by one of the phishing emails sent by Account A.

Figure 5: Timeline of key incidents with Darktrace/Apps actions

Whilst the motive of the threat actor was unclear, this may have been the result of:

  • Credential harvesting for future use against the organization or to sell to a third party.
  • Possible impersonation of compromised users on professional websites (LinkedIn, Indeed) to phish further company accounts:
  • Fake accounts of one user were discovered on LinkedIn.
  • Emails registering for Indeed for this same user were seen during compromise.

How did the attack bypass the rest of the security stack?

  • Compromised Office 365 credentials, combined with the use of the user agent BAV2ROPC meant MFA could not stop the suspicious login.
  • RESPOND was in Human Confirmation Mode and was therefore not confirmed to take autonomous action, showing only the detections. Disabling Account A would likely have prevented the phishing emails and the subsequent compromise of Accounts B and C.
  • The organization was not signed up to Darktrace Proactive Threat Notifications or Ask The Expert services which could have allowed further triage from Darktrace SOC analysts.

Cyber AI Analyst Investigates

Darktrace’s Cyber AI Analyst automates investigations at speed and scale, prioritizing relevant incidents and creating actionable insights, allowing security teams to rapidly understand and act against a threat.

In this case, AI Analyst automatically investigated all three account compromises, saving time for the customer’s security team and allowing them to quickly investigate the incident themselves in more detail. The technology also highlighted some of the viewed files by the compromised accounts which was not immediately obvious from the model breaches alone.

Figure 6: Screenshot of AI Analyst for Account A
Figure 7: Screenshot of AI Analyst for Account B
Figure 8: Screenshot of AI Analyst for Account C

Darktrace RESPOND (Antigena) actions

The organization in question did not have RESPOND/Apps configured in Active Mode, and so it did not take any action in this case. The table below shows the critical defensive actions RESPOND would have taken.[3]

Nonetheless, we can see what actions RESPOND would have taken, and when, had the technology been enabled.

The above tables illustrate that all three users would have been disabled during the incident had RESPOND been active. The highlighted row shows that Account A would have been disabled when the internal phishing emails were sent and possibly then prevented the cascade of compromised email accounts (B and C).

Conclusion

SaaS accounts greatly increase a company’s attack surface. Not only is exploitation of compromised accounts quick, but a single compromised account can easily lead to further compromises via an internal phishing campaign. Together this reinforces the ongoing need for autonomous and proactive security to complement existing IT teams and reduce threats at the point of compromise. Whilst disabling ‘legacy authentication’ for all accounts and providing MFA would give some extra protection, Darktrace/Apps has the ability to block all further infection.

Credit to: Adam Stevens and Anthony Wong for their contributions.

Appendix

List of Darktrace Model Detections

User A – February 9 2022

  • 04:55:51 UTC | SaaS / Access / Suspicious Login User-Agent
  • 04:55:51 UTC | SaaS / Access / Unusual External Source for SaaS Credential Use
  • 04:55:52 UTC | Antigena / SaaS / Antigena Suspicious SaaS and Email Activity Block
  • 04:55:52 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block
  • 14:16:48 UTC | SaaS / Compliance / New Email Rule
  • 14:16:48 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 14:16:49 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 14:16:49 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block
  • 14:45:06 UTC | IaaS / Admin / Azure Application Administration Activities
  • 14:45:07 UTC | SaaS / Admin / OAuth Permission Grant
  • 14:45:07 UTC | Device / Multiple Model Breaches
  • 14:45:08 UTC | SaaS / Compliance / Multiple Unusual SaaS Activities
  • 15:03:25 UTC | SaaS / Email Nexus / Possible Outbound Email Spam
  • 15:03:25 UTC | SaaS / Compromise / Unusual Login and Outbound Email Spam

User B – February 9 2022

  • 15:18:21 UTC | SaaS / Compliance / New Email Rule
  • 15:18:21 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 15:18:22 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 15:18:22 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block

User C – February 10 2022

  • 14:25:20 UTC | SaaS / Admin / OAuth Permission Grant
  • 14:38:09 UTC | SaaS / Compliance / New Email Rule
  • 14:38:09 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 14:38:10 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 14:38:10 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Refrences

1. https://www.ncsc.gov.uk/guidance/phishing#section_3

2. https://www.bleepingcomputer.com/news/security/microsoft-scammers-bypass-office-365-mfa-in-bec-attacks/

3. https://customerportal.darktrace.com/product-guides/main/antigena-saas-inhibitors

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
Laura Leyland
Cyber Analyst

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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].

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:  

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.

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.

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.

[related-resource]

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About the author
Eric Rozon
Senior Security Researcher
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