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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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May 22, 2026

Darktrace named a Leader in the 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR) For the Second Consecutive Year

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Continued recognition in NDR  

Darktrace has been recognized as a Leader in the 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR), marking the second consecutive year in the Leaders quadrant.

We believe this consistency reflects sustained ability to execute, adapt, and deliver outcomes as the market evolves.

While we are immensely proud to be recognized by industry analysts as a Leader in NDR, that's just part of the story. Darktrace was also Named the Only 2025 Gartner® Peer Insights™ Customers’ Choice for Network Detection and Response based on direct customer feedback and real-world experience.

We believe the combination of these two signals is important. One reflects how the market is evaluated. The other reflects how technology performs in practice.

Why Darktrace continues to be recognized as a leader

We believe our position as a Leader for the second consecutive year reflects a combination of our sustained ability to execute in NDR, continued AI innovation, and proven delivery of security outcomes for customers and partners worldwide.

We also feel that our leadership in the NDR market is a testament to our unique and multi-layered AI approach, for which we were recognized as No.7 on Fast Company’s Most Innovative AI Companies of 2026 list, plus one of the hottest AI cybersecurity companies in CRN's AI 100.

Adapting to complex, real-world environments

Organizations are no longer protecting a single network perimeter. They are securing a mix of users, devices, applications, and data that move across hybrid environments.

Darktrace has focused on maintaining visibility and detection across these conditions, allowing security teams to understand activity as it scales.

Supporting organizations globally, not just technically

Security outcomes are shaped as much by deployment and support as they are by detection capability.

Darktrace continues to invest in regional presence across 29 countries around the world, helping organizations operationalize NDR in ways that align with local requirements, internal processes, and team structures.

Continuing to push AI beyond detection

AI in cybersecurity is often positioned as a way to improve detection accuracy. But the more important shift is how AI can influence decision-making and response.

Darktrace continues to develop models that learn from both live environments and historical incident data, combining real-time behavioral analysis with insights derived from prior attack patterns.

Using technologies such as the Incident Graph and DIGEST (Darktrace Incident Graph Evaluation for Security Threats), activity is not analyzed in isolation. Instead, relationships between users, devices, connections, and events are mapped over time, allowing the system to reconstruct how an incident is unfolding and how similar incidents have progressed in the past.

By evaluating these patterns, Darktrace can assess the likelihood that an incident will escalate, prioritizing the activity that poses the greatest risk and surfacing the most relevant context for investigation.

This shifts security operations from simply identifying anomalies to understanding their trajectory, helping teams anticipate potential impact and respond earlier with greater precision.

Why NDR is shifting from reactive detection to proactive, AI-driven security

Traditional approaches to NDR have been built around reactively identifying threats once they become clearly visible. That model is increasingly difficult to rely on.

Attackers are no longer operating in ways that stand out. They use valid credentials, trusted tools, and low-and-slow techniques that blend into everyday activity. By the time something looks obviously malicious, the impact is often already underway.

This is the core limitation of reactive detection. It depends on recognizing something that already looks like a threat.

As a result, many of the most consequential incidents today fall into a gap.

Insider activity, compromised credentials, and novel attacks rarely trigger traditional alerts because they do not follow known patterns. On the surface, they often appear legitimate, making them difficult to distinguish from normal behavior without deeper context.

This is why we believe this Gartner recognition reflects a broader shift in NDR toward autonomous, proactive and pre‑emptive security operations.

By understanding normal behavior within an environment, it is possible to identify subtle deviations rather than waiting for confirmation of threats as they are taking place.

Darktrace’s Self-Learning AI is designed for behavioral understanding. By continuously learning each organization’s normal patterns, it can detect deviations in real time, enabling a proactive and pre-emptive model of NDR where security teams can respond to early signs of risk as they emerge, reducing the window in which attacks can develop.

In multiple cases, this behavioral approach has led to early threat detection where Darktrace identified completely unknown threats, including pre-CVE zero-day activity. By detecting subtle behavioral changes before vulnerabilities were publicly disclosed or widely understood, organizations can mitigate threats before they do damage.

This shift is subtle but important. Modern NDR solutions must shift from a system that explains what happened to one that helps prevent threats from developing in the first place, and Darktrace is proud to be at the forefront of this shift - helping organizations build and maintain a state of proactive network resilience.

Continuing to innovate at the forefront of NDR

In our view, recognition as a Leader reflects where the market is today. Continuing to innovate defines what comes next.

As businesses evolve, new technologies like AI tools and agents introduce new security risks and challenges; security teams need more than simple detection. They need a complete understanding of risk as it develops, the ability to investigate it in context, and to contain threats at machine speed.  

Darktrace / NETWORK is built to deliver across that full spectrum. Its Self-Learning AI continuously adapts to each organization’s environment, identifying subtle behavioral changes that signal emerging threats. Integrated investigation and autonomous response reduce the time between detection and action, allowing teams to move with greater speed and confidence.

This combination enables organizations to detect and contain known, unknown, and insider threats as they develop, while also strengthening resilience over time.

As a two-time Leader in the Gartner® Magic Quadrant™ for NDR and the only 2025 Gartner® Peer Insights™ Customers’ Choice, we feel Darktrace continues to evolve its platform to meet the demands of modern environments, delivering a more complete and adaptive approach to network security.

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Disclaimer: The 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR) ,The 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR), Thomas Lintemuth, Charanpal Bhogal, Nahim Fazal, 18 May 2026.

Gartner does not endorse any vendor, product or service depicted in its research publications, and does not advise technology users to select only those vendors with the highest ratings or other designation. Gartner research publications consist of the opinions of Gartner’s research organization and should not be construed as statements of fact. Gartner disclaims all warranties, expressed or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose.

GARTNER is a registered trademark and service mark of Gartner, Inc. and/or its affiliates in the U.S. and internationally and is used herein with permission. All rights reserved. Magic Quadrant is a registered trademark of Gartner, Inc. and/or its affiliates and is used herein with permission. All rights reserved.

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Mikey Anderson
Product Marketing Manager, Network Detection & Response

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May 21, 2026

Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches

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How enterprise AI Agents are changing the risk landscape  

Generative AI Agents are changing the way work gets done inside enterprises, and subsequently how security risks may emerge. Organizations have quickly realized that providing these agents with wider access to tooling, internal information, and granting permissions for the agent to perform autonomous actions can greatly increase the efficiency of employee workflows.

Early deployments of Generative AI systems led many organizations to scope individual components as self-contained applications: a chat interface, a model, and a prompt, with guardrails placed at the boundary. Research from Gartner has shown that while the volume and scope of Agentic AI deployments in enterprise environments is rapidly accelerating, many of the mechanisms required to manage risk, trust, and cost are still maturing.

The issue now resides on whether an agent can be influenced, misdirected, or manipulated in ways that leads to unsafe behavior across a broader system.

Why prompt security matters in enterprise AI

Prompt security matters in enterprise AI because prompts are the primary way users and systems interact with Agentic AI models, making them one of the earliest and most visible indicators of how these systems are being used and where risk may emerge.

For security teams, prompt monitoring is a logical starting point for understanding enterprise AI usage, providing insight into what types of questions are being asked and tasks are being given to AI Agents, how these systems are being guided, and whether interactions align with expected behavior. Complete prompt security takes this one step further, filtering out or blocking sensitive or dangerous content to prevent risks like prompt injection and data leakage.

However, visibility only at the prompt layer can create a false sense of security. Prompts show what was asked, but not always why it was asked, or what downstream actions were triggered by the agent across connected systems, data sources, or applications.

What prompt security reveals  

The primary function of prompt security is to minimize risks associated with generative and agentic AI use, but monitoring and analysis of prompts can also grant insight into use cases for particular agents and model. With comprehensive prompt security, security teams should be able to answer the following questions for each prompt:

  • What task was the user attempting to complete?
  • What data was included in the request, and was any of the data high-risk or confidential?
  • Was the interaction high-risk, potentially malicious, or in violation of company policy?
  • Was the prompt anomalous (in comparison to previous prompts sent to the agent / model)?

Improving visibility at this layer is a necessary first step, allowing organizations to establish a baseline for how AI systems are being used and where potential risks may exist.  

Prompt security alone does not provide a complete view of risk. Further data is needed to understand how the prompt is interpreted, how context is applied, what autonomous actions the agent takes (if any), or what downstream systems are affected. Understanding the outcome of a query is just as important for complete prompt security as understanding the input prompt itself – for example, a perfectly normal, low-risk prompt may inadvertently result in an agent taking a high-risk action.

Comprehensive AI security systems like Darktrace / SECURE AI can monitor and analyze both the prompt submitted to a Generative AI system, as well as the responses and chain-of-thought of the system, providing greater insight into the behavior of the system. Darktrace / SECURE AI builds on the core Darktrace methodology, learning the expected behaviors of your organization and identifying deviations from the expected pattern of life.

How organizations address prompt security today

As prompt-level visibility has become a focus, a range of approaches have emerged to make this activity more observable and controllable. Various monitoring and logging tools aim to capture prompt inputs to be analyzed after the fact.  

Input validation and filtering systems attempt to intervene earlier, inspecting prompts before they reach the model. These controls look for known jailbreak patterns, language indicative of adversarial attacks, or ambiguous instructions which could push the system off course.

Importantly, for a prompt security solution to be accurate and effective, prompts must be continually observed and governed, rather than treated as a point-in-time snapshot.  

Where prompt security breaks down in real environments

In more complex environments, especially those involving multiple agents or extensive tool use, AI security becomes harder to define and control.

Agent-to-Agent communications can be harder to monitor and trace as these happen without direct user interaction. Communication between agents can create routes for potential context leakage between agents, unintentional privilege escalation, or even data leakage from a higher privileged agent to a lower privileged one.

Risk is shaped not just by what is asked, but by the conditions in which that prompt operates and the actions an agent takes. Controls at the orchestration layer are starting to reflect this reality. Techniques such as context isolation, scoped memory, and role-based boundaries aim to limit how far a prompt’s influence can extend.  

Furthermore, Shadow AI usage can be difficult to monitor. AI systems that are deployed outside of formal governance structures and Generative AI systems hosted on unknown endpoints can fly under the radar and can go unseen by monitoring tools, leaving a critical opening where adversarial prompts may go undetected. Darktrace / SECURE AI features comprehensive detection of Shadow AI usage, helping organizations identify potential risk areas.

How prompt security fits in a broader AI risk model

Prompt security is an important starting point, but it is not a complete security strategy. As AI systems become more integrated into enterprise environments, the risks extend to what resources the system can access, how it interprets context, and what actions it is allowed to take across connected tools and workflows.

This creates a gap between visibility and control. Prompt security alone allows security teams to observe prompt activity but falls short of creating a clear understanding of how that activity translates into real-world impact across the organization.

Closing that gap requires a broader approach, one that connects signals across human and AI agent identities, SaaS, cloud, and endpoint environments. It means understanding not just how an AI system is being used, but how that usage interacts with the rest of the digital estate.

Prompt security, in that sense, is less of a standalone solution and more of an entry point into a larger problem: securing AI across the enterprise as a whole.

Explore how Darktrace / SECURE AI brings prompt security to enterprises

Darktrace brings more than a decade of AI expertise, built on an enterprise‑wide platform designed to operate in and understand the behaviors of the complex, ambiguous environments where today’s AI now lives. With Darktrace / SECURE AI, enterprises can safely adopt, manage, monitor, and build AI within their business.  

Learn about Darktrace / SECURE AI here.

Sign up today to stay informed about innovations across securing AI.

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Jamie Bali
Technical Author (AI) Developer
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