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September 23, 2025

ShadowV2: An emerging DDoS for hire botnet

Darktrace exposed a cybercrime-as-a-service campaign using Python and Go-based malware, Docker containerization, and a full operator UI. With DDoS-as-a-service features, modular APIs, and advanced evasion, this platform highlights the need for defenders to monitor cloud workloads, container orchestration, and API activity to counter evolving threats.
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
Nate Bill
Threat Researcher
ShadowV2: An emerging DDoS for hire botnet Default blog image
23
Sep 2025

Introduction: ShadowV2 DDoS

Darktrace's latest investigation uncovered a novel campaign that blends traditional malware with modern devops technology.

At the center of this campaign is a Python-based command-and-control (C2) framework hosted on GitHub CodeSpaces. This campaign also utilizes a Python based spreader with a multi-stage Docker deployment as the initial access vector.

The campaign further makes use of a Go-based Remote Access Trojan (RAT) that implements a RESTful registration and polling mechanism, enabling command execution and communication with its operators.

ShadowV2 attack techniques

What sets this campaign apart is the sophistication of its attack toolkit.

The threat actors employ advanced methods such as HTTP/2 rapid reset, a Cloudflare under attack mode (UAM) bypass, and large-scale HTTP floods, demonstrating a capability to combine distributed denial-of-service (DDoS) techniques with targeted exploitation.

With the inclusion of an OpenAPI specification, implemented with FastAPI and Pydantic and a fully developed login panel and operator interface, the infrastructure seems to resemble a “DDoS-as-a-service” platform rather than a traditional botnet, showing the extent to which modern malware increasingly mirrors legitimate cloud-native applications in both design and usability.

Analysis of a ShadowV2 attack

Initial access

The initial compromise originates from a Python script hosted on GitHub CodeSpaces. This can be inferred from the observed headers:

User-Agent: docker-sdk-python/7.1.0

X-Meta-Source-Client: github/codespaces

The user agent shows that the attacker is using the Python Docker SDK, a library for Python programs that allows them to interact with Docker to create containers. The X-Meta-Source-Client appears to have been injected by GitHub into the request to allow for attribution, although there is no documentation online about this header.

The IP the connections originate from is 23.97.62[.]139, which is a Microsoft IP based in Singapore. This aligns with expectations as GitHub is owned by Microsoft.

This campaign targets exposed Docker daemons, specifically those running on AWS EC2. Darktrace runs a number of honeypots across multiple cloud providers and has only observed attacks against honeypots running on AWS EC2. By default, Docker is not accessible to the Internet, however, can be configured to allow external access. This can be useful for managing complex deployments where remote access to the Docker API is needed.

Typically, most campaigns targeting Docker will either take an existing image from Docker Hub and deploy their tools within it, or upload their own pre-prepared image to deploy. This campaign works slightly differently; it first spawns a generic “setup” container and installs a number of tools within it. This container is then imaged and deployed as a live container with the malware arguments passed in via environmental variables.

Attacker creates a blank container from an Ubuntu image.
Figure 1: Attacker creates a blank container from an Ubuntu image.
Attacker sets up their tools for the attack.
Figure 2: Attacker sets up their tools for the attack.
 Attacker deploys a new container using the image from the setup container.
Figure 3: Attacker deploys a new container using the image from the setup container.

It is unclear why the attackers chose this approach - one possibility is that the actor is attempting to avoid inadvertently leaving forensic artifacts by performing the build on the victim machine, rather than building it themselves and uploading it.

Malware analysis

The Docker container acts as a wrapper around a single binary, dropped in /app/deployment. This is an ELF binary written in Go, a popular choice for modern malware. Helpfully, the binary is unstripped, making analysis significantly easier.

The current version of the malware has not been reported by OSINT providers such as VirusTotal. Using the domain name from the MASTER_ADDR variable and other IoCs, we were able to locate two older versions of the malware that were submitted to VirusTotal on the June 25 and July 30 respectively [1] [2].  Neither of these had any detections and were only submitted once each using the web portal from the US and Canada respectively. Darktrace first observed the attack against its honeypot on June 24, so it could be a victim of this campaign submitting the malware to VirusTotal. Due to the proximity of the start of the attacks, it could also be the attacker testing for detections, however it is not possible to know for certain.

The malware begins by phoning home, using the MASTER_ADDR and VPS_NAME identifiers passed in from the Docker run environmental variables. In addition, the malware derives a unique VPS_ID, which is the VPS_NAME concatenated with the current unix timestamp. The VPS_ID is used for all communications with the C2 server as the identifier for the specific implant. If the malware is restarted, or the victim is re-infected, the C2 server will inform the implant of its original VPS_ID to ensure continuity.

Snippet that performs the registration by sending a POST request to the C2 API with a JSON structure.
Figure 4: Snippet that performs the registration by sending a POST request to the C2 API with a JSON structure.

From there, the malware then spawns two main loops that will remain active for the lifetime of the implant. Every second, it sends a heartbeat to the C2 by sending the VPS_ID to hxxps://shadow.aurozacloud[.]xyz/api/vps/heartbeat via POST request. Every 5 seconds, it retrieves hxxps://shadow.aurozacloud[.]xyz/api/vps/poll/<VPS ID> via a GET request to poll for new commands.

The poll mechanism shadow v2
Figure 5: The poll mechanism.

At this stage, Darktrace security researchers wrote a custom client that ran on the server infected by the attacker that mimicked their implant. The goal was to intercept commands from the C2. Based on this, it was observed initiating an attack against chache08[.]werkecdn[.]me using a 120 thread HTTP2 rapid reset attack. This site appears to be hosted on an Amsterdam VPS provided by FDCServers, a server hosting company. It was not possible to identify what normally runs on this site, as it returns a 403 Forbidden error when visited.

Darktrace’s code analysis found that the returned commands contain the following fields:

  • Method (e.g. GET, POST)
  • A unique ID for the attack
  • A URL endpoint used to report attack statistics
  • The target URL & port
  • The duration of the attack
  • The number of threads to use
  • An optional proxy to send HTTP requests through

The malware then spins up several threads, each running a configurable number of HTTP clients using Valyala’s fasthttp library, an open source Go library for making high-performance HTTP requests. After this is complete, it uses these clients to perform an HTTP flood attack against the target.

A snippet showing the fasthttp client creation loop, as well as a function to report the worker count back to the C2.
Figure 6: A snippet showing the fasthttp client creation loop, as well as a function to report the worker count back to the C2.

In addition, it also features several flags to enable different bypass mechanisms to augment the malware:

  • WordPress bypass (does not appear to be implemented - the flag is not used anywhere)
  • Random query strings appended to the URL
  • Spoofed forwarding headers with random IP addresses
  • Cloudflare under-attack-mode (UAM) bypass
  • HTTP2 rapid reset

The most interesting of these is the Cloudflare UAM bypass mechanism. When this is enabled, the malware will attempt to use a bundled ChromeDP binary to solve the Cloudflare JavaScript challenge that is presented to new visitors. If this succeeds, the clearance cookie obtained is then included in subsequent requests. This is unlikely to work in most cases as headless Chrome browsers are often flagged, and a regular CAPTCHA is instead served.

The UAM bypass success snippet.
Figure 7: The UAM bypass success snippet.

Additionally, the malware has a flag to enable an HTTP2 rapid reset attack mode instead of a regular HTTP flood. In HTTP2, a client can create thousands of requests within a single connection using multiplexing, allowing sites to load faster. The number of request streams per connection is capped however, so in a rapid reset attack many requests are made and then immediately cancelled to allow more requests to be created. This allows a single client to execute vastly more requests per second and use more server resources than it otherwise would, allowing for more effective denial-of-service (DoS) attacks.

 The HTTP2 rapid reset snippet from the main attack function.
Figure 8: The HTTP2 rapid reset snippet from the main attack function.

API/C2 analysis

As mentioned throughout the malware analysis section, the malware communicates with a C2 server using HTTP. The server is behind Cloudflare, which obscures its hosting location and prevents analysis. However, based on analysis of the spreader, it's likely running on GitHub CodeSpaces.

When sending a malformed request to the API, an error generated by the Pydantic library is returned:

{"detail":[{"type":"missing","loc":["body","vps_id"],"msg":"Field required","input":{"vps_name":"xxxxx"},"url":"https://errors.pydantic.dev/2.11/v/missing"}]}

This shows they are using Python for the API, which is the same language that the spreader is written in.

One of the larger frameworks that ships with Pydantic is FastAPI, which also ships with Swagger. The malware author left this publicly exposed, and Darktrace’s researchers were able to obtain a copy of their API documentation. The author appears to have noticed this however, as subsequent attempts to access it now returns a HTTP 404 Not Found error.

Swagger UI view based on the obtained OpenAPI spec.
Figure 9: Swagger UI view based on the obtained OpenAPI spec.

This is useful to have as it shows all the API endpoints, including the exact fields they take and return, along with comments on each endpoint written by the attacker themselves.

It is very likely a DDoS for hire platform (or at the very least, designed for multi-tenant use) based on the extensive user API, which features authentication, distinctions between privilege level (admin vs user), and limitations on what types of attack a user can execute. The screenshot below shows the admin-only user create endpoint, with the default limits.

The admin-only user create endpoint shadow v2
Figure 10: The admin-only user create endpoint.

The endpoint used to launch attacks can also be seen, which lines up with the options previously seen in the malware itself. Interestingly, this endpoint requires a list of zombie systems to launch the attack from. This is unusual as most DDoS for hire services will decide this internally or just launch the attack from every infected host (zombie). No endpoints that returned a list of zombies were found, however, it’s possible one exists as the return types are not documented for all the API endpoints.

The attack start endpoint shadow v2
Figure 11: The attack start endpoint.

There is also an endpoint to manage a blacklist of hosts that cannot be attacked. This could be to stop users from launching attacks against sites operated by the malware author, however it’s also possible the author could be attempting to sell protection to victims, which has been seen previously with other DDoS for hire services.

Blacklist endpoints shadow v2 DDoS
Figure 12: Blacklist endpoints.

Attempting to visit shadow[.]aurozacloud[.]xyz results in a seizure notice. It is most likely fake the same backend is still in use and all of the API endpoints continue to work. Appending /login to the end of the path instead brings up the login screen for the DDoS platform. It describes itself as an “advanced attack platform”, which highlights that it is almost certainly a DDoS for hire service. The UI is high quality, written in Tailwind, and even features animations.

The fake seizure notice.
Figure 13: The fake seizure notice.
The login UI at /login.
Figure 14: The login UI at /login.

Conclusion

By leveraging containerization, an extensive API, and with a full user interface, this campaign shows the continued development of cybercrime-as-a-service. The ability to deliver modular functionality through a Go-based RAT and expose a structured API for operator interaction highlights how sophisticated some threat actors are.

For defenders, the implications are significant. Effective defense requires deep visibility into containerized environments, continuous monitoring of cloud workloads, and behavioral analytics capable of identifying anomalous API usage and container orchestration patterns. The presence of a DDoS-as-a-service panel with full user functionality further emphasizes the need for defenders to think of these campaigns not as isolated tools but as evolving platforms.

Appendices

References

1. https://www.virustotal.com/gui/file/1b552d19a3083572bc433714dfbc2b75eb6930a644696dedd600f9bd755042f6

2. https://www.virustotal.com/gui/file/1f70c78c018175a3e4fa2b3822f1a3bd48a3b923d1fbdeaa5446960ca8133e9c

IoCs

Malware hashes (SHA256)

●      2462467c89b4a62619d0b2957b21876dc4871db41b5d5fe230aa7ad107504c99

●      1b552d19a3083572bc433714dfbc2b75eb6930a644696dedd600f9bd755042f6

●      1f70c78c018175a3e4fa2b3822f1a3bd48a3b923d1fbdeaa5446960ca8133e9c

C2 domain

●      shadow.aurozacloud[.]xyz

Spreader IPs

●      23.97.62[.]139

●      23.97.62[.]136

Yara rule

rule ShadowV2 {

meta:

author = "[email protected]"

description = "Detects ShadowV2 botnet implant"

strings:

$string1 = "shadow-go"

$string2 = "shadow.aurozacloud.xyz"

$string3 = "[SHADOW-NODE]"

$symbol1 = "main.registerWithMaster"

$symbol2 = "main.handleStartAttack"

$symbol3 = "attacker.bypassUAM"

$symbol4 = "attacker.performHTTP2RapidReset"

$code1 = { 48 8B 05 ?? ?? ?? ?? 48 8B 1D ?? ?? ?? ?? E8 ?? ?? ?? ?? 48 8D 0D ?? ?? ?? ?? 48 89 8C 24 38 01 00 00 48 89 84 24 40 01 00 00 48 8B 4C 24 40 48 BA 00 09 6E 88 F1 FF FF FF 48 8D 04 0A E8 ?? ?? ?? ?? 48 8D 0D ?? ?? ?? ?? 48 89 8C 24 48 01 00 00 48 89 84 24 50 01 00 00 48 8D 05 ?? ?? ?? ?? BB 05 00 00 00 48 8D 8C 24 38 01 00 00 BF 02 00 00 00 48 89 FE E8 ?? ?? ?? ?? }

$code2 = { 48 89 35 ?? ?? ?? ?? 0F B6 94 24 80 02 00 00 88 15 ?? ?? ?? ?? 0F B6 94 24 81 02 00 00 88 15 ?? ?? ?? ?? 0F B6 94 24 82 02 00 00 88 15 ?? ?? ?? ?? 0F B6 94 24 83 02 00 00 88 15 ?? ?? ?? ?? 48 8B 05 ?? ?? ?? ?? }

$code3 = { 48 8D 15 ?? ?? ?? ?? 48 89 94 24 68 04 00 00 48 C7 84 24 78 04 00 00 15 00 00 00 48 8D 15 ?? ?? ?? ?? 48 89 94 24 70 04 00 00 48 8D 15 ?? ?? ?? ?? 48 89 94 24 80 04 00 00 48 8D 35 ?? ?? ?? ?? 48 89 B4 24 88 04 00 00 90 }

condition:

uint16(0) == 0x457f and (2 of ($string*) or 2 of ($symbol*) or any of ($code*))

}

The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.

Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.

Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.

The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content without notice.

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
Nate Bill
Threat Researcher

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August 11, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product

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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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About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
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