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April 5, 2022

Explore Internet-Facing System Vulnerabilities

Read about 2021's top four incidents and how Darktrace's advanced threat detection technology identified and mitigated vulnerabilities. Learn more.
Written by
Sam Lister
Specialist Security Researcher
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
Sam Lister
Specialist Security Researcher
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05
Apr 2022

By virtue of their exposure, Internet-facing systems (i.e., systems which have ports open/exposed to the wider Internet) are particularly susceptible to compromise. Attackers typically compromise Internet-facing systems by exploiting zero-day vulnerabilities in applications they run. During 2021, critical zero-day vulnerabilities in the following applications were publicly disclosed:

Internet-facing systems running these applications were consequently heavily targeted by attackers. In this post, we will provide examples of compromises of these systems observed by Darktrace’s SOC team in 2021. As will become clear, successful exploitation of weaknesses in Internet-facing systems inevitably results in such systems doing things which they do not normally do. Rather than focusing on identifying attempts to exploit these weaknesses, Darktrace focuses on identifying the unusual behaviors which inevitably ensue. The purpose of this post is to highlight the effectiveness of this approach.

Exchange server compromise

In January, researchers from the cyber security company DEVCORE reported a series of critical vulnerabilities in Microsoft Exchange which they dubbed ‘ProxyLogon’.[1] ProxyLogon consists of a server-side request forgery (SSRF) vulnerability (CVE-2021-26855) and a remote code execution (RCE) vulnerability (CVE-2021-27065). Attackers were observed exploiting these vulnerabilities in the wild from as early as January 6.[2] In April, DEVCORE researchers reported another series of critical vulnerabilities in Microsoft Exchange which they dubbed ‘ProxyShell’.[3] ProxyShell consists of a pre-authentication path confusion vulnerability (CVE-2021-34473), a privilege elevation vulnerability (CVE-2021-34523), and a post-authentication RCE vulnerability (CVE-2021-31207). Attackers were first observed exploiting these vulnerabilities in the wild in August.[4] In many cases, attackers exploited the ProxyShell and ProxyLogon vulnerabilities in order to create web shells on the targeted Exchange servers. The presence of these web shells provided attackers with the means to remotely execute commands on the compromised servers.

In early August 2021, by exploiting the ProxyShell vulnerabilities, an attacker gained the rights to remotely execute PowerShell commands on an Internet-facing Exchange server within the network of a US-based transportation company. The attacker subsequently executed a number of PowerShell commands on the server. One of these commands caused the server to make a 28-minute-long SSL connection to a highly unusual external endpoint. Within a couple of hours, the attacker managed to strengthen their foothold within the network by installing AnyDesk and CobaltStrike on several internal devices. In mid-August, the attacker got the devices on which they had installed Cobalt Strike to conduct network reconnaissance and to transfer terabytes of data to the cloud storage service, MEGA. At the end of August, the attacker got the devices on which they had installed AnyDesk to execute Conti ransomware and to spread executable files and script files to further internal devices.

In this example, the attacker’s exploitation of ProxyShell immediately resulted in the Exchange Server making a long SSL connection to an unusual external endpoint. This connection caused the model Device / Long Agent Connection to New Endpoint to breach. The subsequent reconnaissance, lateral movement, C2, external data transfer, and encryption behavior brought about by the attacker were also picked up by Darktrace’s models.

A non-exhaustive list of the models that breached as a result of the behavior brought about by the attacker:

  • Device / Long Agent Connection to New Endpoint
  • Device / ICMP Address Scan
  • Anomalous Connection / SMB Enumeration
  • Anomalous Server Activity / Outgoing from Server
  • Compromise / Beacon to Young Endpoint
  • Anomalous Server Activity / Rare External from Server
  • Compromise / Fast Beaconing to DGA
  • Compromise / SSL or HTTP Beacon
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Beacon for 4 Days
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Compliance / SMB Drive Write
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Connection / Suspicious Read Write Ratio
  • Anomalous Connection / Suspicious Read Write Ratio and Unusual SMB
  • Anomalous Connection / Sustained MIME Type Conversion
  • Unusual Activity / Anomalous SMB Move & Write
  • Unusual Activity / Unusual Internal Data Volume as Client or Server
  • Device / Suspicious File Writes to Multiple Hidden SMB Shares
  • Compromise / Ransomware / Suspicious SMB Activity
  • Anomalous File / Internal / Unusual SMB Script Write
  • Anomalous File / Internal / Masqueraded Executable SMB Write
  • Device / SMB Lateral Movement
  • Device / Multiple Lateral Movement Model Breaches

Confluence server compromise

Atlassian’s Confluence is an application which provides the means for building collaborative, virtual workspaces. In the era of remote working, the value of such an application is undeniable. The public disclosure of a critical remote code execution (RCE) vulnerability (CVE-2021-26084) in Confluence in August 2021 thus provided a prime opportunity for attackers to cause havoc. The vulnerability, which arises from the use of Object-Graph Navigation Language (OGNL) in Confluence’s tag system, provides attackers with the means to remotely execute code on vulnerable Confluence server by sending a crafted HTTP request containing a malicious parameter.[5] Attackers were first observed exploiting this vulnerability towards the end of August, and in the majority of cases, attackers exploited the vulnerability in order to install crypto-mining tools onto vulnerable servers.[6]

At the beginning of September 2021, an attacker was observed exploiting CVE-2021-26084 in order to install the crypto-mining tool, XMRig, as well as a shell script, onto an Internet-facing Confluence server within the network of an EMEA-based television and broadcasting company. Within a couple of hours, the attacker installed files associated with the crypto-mining malware, Kinsing, onto the server. The Kinsing-infected server then immediately began to communicate over HTTP with the attacker’s C2 infrastructure. Around the time of this activity, the server was observed using the MinerGate crypto-mining protocol, indicating that the server had begun to mine cryptocurrency.

In this example, the attacker’s exploitation of CVE-2021-26084 immediately resulted in the Confluence server making an HTTP GET request with an unusual user-agent string (one associated with curl in this case) to a rare external IP. This behavior caused the models Device / New User Agent, Anomalous Connection / New User Agent to IP Without Hostname, and Anomalous File / Script from Rare Location to breach. The subsequent file downloads, C2 traffic and crypto-mining activity also resulted in several models breaching.

A non-exhaustive list of the models which breached as a result of the unusual behavior brought about by the attacker:

  • Device / New User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / Script from Rare Location
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Internet Facing System File Download
  • Device / Initial Breach Chain Compromise
  • Anomalous Connection / Posting HTTP to IP Without Hostname
  • Compliance / Crypto Currency Mining Activity
  • Compromise / High Priority Crypto Currency Mining
  • Device / Internet Facing Device with High Priority Alert

GitLab server compromise

GitLab is an application providing services ranging from project planning to source code management. Back in April 2021, a critical RCE vulnerability (CVE-2021-22205) in GitLab was publicly reported by a cyber security researcher via the bug bounty platform, HackerOne.[7] The vulnerability, which arises from GitLab’s use of ExifTool for removing metadata from image files, [8] enables attackers to remotely execute code on vulnerable GitLab servers by uploading specially crafted image files.[9] Attackers were first observed exploiting CVE-2021-22205 in the wild in June/July.[10] A surge in exploitations of the vulnerability was observed at the end of October, with attackers exploiting the flaw in order to assemble botnets.[11] Darktrace observed a significant number of cases in which attackers exploited the vulnerability in order to install crypto-mining tools onto vulnerable GitLab servers.

On October 29, an attacker successfully exploited CVE-2021-22205 on an Internet-facing GitLab server within the network of a UK-based education provider. The organization was trialing Darktrace when this incident occurred. The attacker installed several executable files and shell scripts onto the server by exploiting the vulnerability. The attacker communicated with the compromised server (using unusual ports) for several days, before making the server transfer large volumes of data externally and download the crypto-mining tool, XMRig, as well as the botnet malware, Mirai. The server was consequently observed making connections to the crypto-mining pool, C3Pool.

In this example, the attacker’s exploitation of the vulnerability in GitLab immediately resulted in the server making an HTTP GET request with an unusual user-agent string (one associated with Wget in this case) to a rare external IP. The models Anomalous Connection / New User Agent to IP Without Hostname and Anomalous File / EXE from Rare External Location breached as a result of this behavior. The attacker’s subsequent activity on the server over the next few days resulted in frequent model breaches.

A non-exhaustive list of the models which breached as a result of the attacker’s activity on the server:

  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations
  • Anomalous File / Internet Facing Device with High Priority Alert
  • Anomalous File / Script from Rare Location
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Anomalous Connection / Anomalous SSL without SNI to New External
  • Device / Initial Breach Chain Compromise
  • Unusual Activity / Unusual External Data to New IPs
  • Anomalous Server Activity / Outgoing from Server
  • Device / Large Number of Model Breaches from Critical Network Device
  • Anomalous Connection / Data Sent to Rare Domain
  • Compromise / Suspicious File and C2
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Compliance / Crypto Currency Mining Activity
  • Compliance / High Priority Crypto Currency Mining
  • Anomalous File / Zip or Gzip from Rare External Location
  • Compromise / Monero Mining
  • Device / Internet Facing Device with High Priority Alert
  • Anomalous Server Activity / Rare External from Server
  • Compromise / Slow Beaconing Activity To External Rare
  • Compromise / Beaconing Activity To External Rare
  • Compromise / HTTP Beaconing to Rare Destination
  • Compromise / High Volume of Connections with Beacon Score
  • Anomalous File / Numeric Exe Download

Log4j server compromise

On December 9 2021, a critical RCE vulnerability (dubbed ‘Log4Shell’) in version 2 of Apache’s Log4j was publicly disclosed by researchers at LunaSec.[12] As a logging library present in potentially millions of Java applications,[13] Log4j constitutes an obscured, yet ubiquitous feature of the digital world. The vulnerability (CVE-2021-44228), which arises from Log4j’s Java Naming and Directory Interface (JNDI) Lookup feature, enables an attacker to make a vulnerable server download and execute a malicious Java class file. To exploit the vulnerability, all the attacker must do is submit a specially crafted JNDI lookup request to the server. The fact that Log4j is present in so many applications and that the exploitation of this vulnerability is so simple, Log4Shell has been dubbed the ‘most critical vulnerability of the last decade’.[14] Attackers have been exploiting Log4Shell in the wild since at least December 1.[15] Since then, attackers have been observed exploiting the vulnerability to install crypto-mining tools, Cobalt Strike, and RATs onto vulnerable servers.[16]

On December 10, one day after the public disclosure of Log4Shell, an attacker successfully exploited the vulnerability on a vulnerable Internet-facing server within the network of a US-based architecture company. By exploiting the vulnerability, the attacker managed to get the server to download and execute a Java class file named ‘Exploit69ogQNSQYz.class’. Executing the code in this file caused the server to download a shell script file and a file related to the Kinsing crypto-mining malware. The Kinsing-infected server then went on to communicate over HTTP with a C2 server. Since the customer was using the Proactive Threat Notification (PTN) service, they were immediately alerted to this activity, and the server was subsequently quarantined, preventing crypto-mining activity from taking place.

In this example, the attacker’s exploitation of the zero-day vulnerability immediately resulted in the vulnerable server making an HTTP GET request with an unusual user-agent string (one associated with Java in this case) to a rare external IP. The models Anomalous Connection / Callback on Web Facing Device and Anomalous Connection / New User Agent to IP Without Hostname breached as a result of this behavior. The device’s subsequent file downloads and C2 activity caused several Darktrace models to breach.

A non-exhaustive list of the models which breached as a result of the unusual behavior brought about by the attacker:

  • Anomalous Connection / Callback on Web Facing Device
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / Internet Facing System File Download
  • Anomalous File / Script from Rare External Location
  • Device / Initial Breach Chain Compromise
  • Anomalous Connection / Posting HTTP to IP Without Hostname

Round-up

It is inevitable that attackers will attempt to exploit zero-day vulnerabilities in applications running on Internet-facing devices. Whilst identifying these attempts is useful, the fact that attackers regularly exploit new zero-days makes the task of identifying attempts to exploit them akin to a game of whack-a-mole. Whilst it is uncertain which zero-day vulnerability attackers will exploit next, what is certain is that their exploitation of it will bring about unusual behavior. No matter the vulnerability, whether it be a vulnerability in Microsoft Exchange, Confluence, GitLab, or Log4j, Darktrace will identify the unusual behaviors which inevitably result from its exploitation. By identifying unusual behaviors displayed by Internet-facing devices, Darktrace thus makes it almost impossible for attackers to successfully exploit zero-day vulnerabilities without being detected.

For Darktrace customers who want to find out more about detecting potential compromises of internet-facing devices, refer here for an exclusive supplement to this blog.

Thanks to Andy Lawrence for his contributions.

Footnotes

1. https://devco.re/blog/2021/08/06/a-new-attack-surface-on-MS-exchange-part-1-ProxyLogon/

2. https://www.volexity.com/blog/2021/03/02/active-exploitation-of-microsoft-exchange-zero-day-vulnerabilities/

3. https://www.zerodayinitiative.com/blog/2021/8/17/from-pwn2own-2021-a-new-attack-surface-on-microsoft-exchange-proxyshell

4. https://www.rapid7.com/blog/post/2021/08/12/proxyshell-more-widespread-exploitation-of-microsoft-exchange-servers/

5. https://www.kaspersky.co.uk/blog/confluence-server-cve-2021-26084/23376/

6. https://www.bleepingcomputer.com/news/security/atlassian-confluence-flaw-actively-exploited-to-install-cryptominers/

7. https://hackerone.com/reports/1154542

8. https://security.humanativaspa.it/gitlab-ce-cve-2021-22205-in-the-wild/

9.https://about.gitlab.com/releases/2021/04/14/security-release-gitlab-13-10-3-released/

10. https://www.rapid7.com/blog/post/2021/11/01/gitlab-unauthenticated-remote-code-execution-cve-2021-22205-exploited-in-the-wild/

11. https://www.hackmageddon.com/2021/12/16/1-15-november-2021-cyber-attacks-timeline/

12. https://www.lunasec.io/docs/blog/log4j-zero-day/

13. https://www.csoonline.com/article/3644472/apache-log4j-vulnerability-actively-exploited-impacting-millions-of-java-based-apps.html

14. https://www.theguardian.com/technology/2021/dec/10/software-flaw-most-critical-vulnerability-log-4-shell

15. https://www.rapid7.com/blog/post/2021/12/15/the-everypersons-guide-to-log4shell-cve-2021-44228/

16. https://www.microsoft.com/security/blog/2021/12/11/guidance-for-preventing-detecting-and-hunting-for-cve-2021-44228-log4j-2-exploitation/

Written by
Sam Lister
Specialist Security Researcher
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
Sam Lister
Specialist Security Researcher

Why Trust is the New Attack Surface: Darktrace’s Mid-Year Threat Update 2026

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August 3, 2026
Nathaniel Jones
SVP, Global Threat Intelligence
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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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Carlo Loregian
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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

microsoft darktrace integrationDefault blog imageDefault blog image

AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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