Blog
/
Network
/
February 3, 2026

Darktrace Malware Analysis: Unpacking SnappyBee

his blog details how to unpack malware like SnappyBee, a modular backdoor linked to Salt Typhoon, revealing its custom packing, DLL sideloading, dynamic API resolution, and multi‑stage in‑memory decryption. It provides analysts with a step‑by‑step guide to extract hidden payloads and understand advanced evasion techniques by sophisticated malware strains.
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
Nathaniel Bill
Malware Research Engineer
darktace malware analysis snappybeeDefault blog image
03
Feb 2026

Introduction

The aim of this blog is to be an educational resource, documenting how an analyst can perform malware analysis techniques such as unpacking. This blog will demonstrate the malware analysis process against well-known malware, in this case SnappyBee.

SnappyBee (also known as Deed RAT) is a modular backdoor that has been previously attributed to China-linked cyber espionage group Salt Typhoon, also known as Earth Estries [1] [2]. The malware was first publicly documented by TrendMicro in November 2024 as part of their investigation into long running campaigns targeting various industries and governments by China-linked threat groups.

In these campaigns, SnappyBee is deployed post-compromise, after the attacker has already obtained access to a customer's system, and is used to establish long-term persistence as well as deploying further malware such as Cobalt Strike and the Demodex rootkit.

To decrease the chance of detection, SnappyBee uses a custom packing routine. Packing is a common technique used by malware to obscure its true payload by hiding it and then stealthily loading and executing it at runtime. This hinders analysis and helps the malware evade detection, especially during static analysis by both human analysts and anti-malware services.

This blog is a practical guide on how an analyst can unpack and analyze SnappyBee, while also learning the necessary skills to triage other malware samples from advanced threat groups.

First principles

Packing is not a new technique, and threat actors have generally converged on a standard approach. Packed binaries typically feature two main components: the packed data and an unpacking stub, also called a loader, to unpack and run the data.

Typically, malware developers insert a large blob of unreadable data inside an executable, such as in the .rodata section. This data blob is the true payload of the malware, but it has been put through a process such as encryption, compression, or another form of manipulation to render it unreadable. Sometimes, this data blob is instead shipped in a different file, such as a .dat file, or a fake image. When this happens, the main loader has to read this using a syscall, which can be useful for analysis as syscalls can be easily identified, even in heavily obfuscated binaries.

In the main executable, malware developers will typically include an unpacking stub that takes the data blob, performs one or more operations on it, and then triggers its execution. In most samples, the decoded payload data is loaded into a newly allocated memory region, which will then be marked as executable and executed. In other cases, the decoded data is instead dropped into a new executable on disk and run, but this is less common as it increases the likelihood of detection.

Finding the unpacking routine

The first stage of analysis is uncovering the unpacking routine so it can be reverse engineered. There are several ways to approach this, but it is traditionally first triaged via static analysis on the initial stages available to the analyst.

SnappyBee consists of two components that can be analyzed:

  • A Dynamic-link Library (DLL) that acts as a loader, responsible for unpacking the malicious code
  • A data file shipped alongside the DLL, which contains the encrypted malicious code

Additionally, SnappyBee includes a legitimate signed executable that is vulnerable to DLL side-loading. This means that when the executable is run, it will inadvertently load SnappyBee’s DLL instead of the legitimate one it expects. This allows SnappyBee to appear more legitimate to antivirus solutions.

The first stage of analysis is performing static analysis of the DLL. This can be done by opening the DLL within a disassembler such as IDA Pro. Upon opening the DLL, IDA will display the DllMain function, which is the malware’s initial entry point and the first code executed when the DLL is loaded.

The DllMain function
Figure 1: The DllMain function

First, the function checks if the variable fdwReason is set to 1, and exits if it is not. This variable is set by Windows to indicate why the DLL was loaded. According to Microsoft Developer Network (MSDN), a value of 1 corresponds to DLL_PROCESS_ATTACH, meaning “The DLL is being loaded into the virtual address space of the current process as a result of the process starting up or as a result of a call to LoadLibrary” [3]. Since SnappyBee is known to use DLL sideloading for execution, DLL_PROCESS_ATTACH is the expected value when the legitimate executable loads the malicious DLL.

SnappyBee then uses the GetModule and GetProcAddress to dynamically resolve the address of the VirtualProtect in kernel32 and StartServiceCtrlDispatcherW in advapi32. Resolving these dynamically at runtime prevents them from showing up as a static import for the module, which can help evade detection by anti-malware solutions. Different regions of memory have different permissions to control what they can be used for, with the main ones being read, write, and execute. VirtualProtect is a function that changes the permissions of a given memory region.

SnappyBee then uses VirtualProtect to set the memory region containing the code for the StartServiceCtrlDispatcherW function as writable. It then inserts a jump instruction at the start of this function, redirecting the control flow to one of the SnappyBee DLL’s other functions, and then restores the old permissions.

In practice, this means when the legitimate executable calls StartServiceCtrlDispatcherW, it will immediately hand execution back to SnappyBee. Meanwhile, the call stack now appears more legitimate to outside observers such as antimalware solutions.

The hooked-in function then reads the data file that is shipped with SnappyBee and loads it into a new memory allocation. This pattern of loading the file into memory likely means it is responsible for unpacking the next stage.

The start of the unpacking routine that reads in dbindex.dat.
Figure 2: The start of the unpacking routine that reads in dbindex.dat.

SnappyBee then proceeds to decrypt the memory allocation and execute the code.

The memory decryption routine.
Figure 3: The memory decryption routine.

This section may look complex, however it is fairly straight forward. Firstly, it uses memset to zero out a stack variable, which will be used to store the decryption key. It then uses the first 16 bytes of the data file as a decryption key to initialize the context from.

SnappyBee then calls the mbed_tls_arc4_crypt function, which is a function from the mbedtls library. Documentation for this function can be found online and can be referenced to better understand what each of the arguments mean [4].

The documentation for mbedtls_arc4_crypt.
Figure 4: The documentation for mbedtls_arc4_ crypt.

Comparing the decompilation with the documentation, the arguments SnappyBee passes to the function can be decoded as:

  • The context derived from 16-byte key at the start of the data is passed in as the context in the first parameter
  • The file size minus 16 bytes (to account for the key at the start of the file) is the length of the data to be decrypted
  • A pointer to the file contents in memory, plus 16 bytes to skip the key, is used as the input
  • A pointer to a new memory allocation obtained from VirtualAlloc is used as the output

So, putting it all together, it can be concluded that SnappyBee uses the first 16 bytes as the key to decrypt the data that follows , writing the output into the allocated memory region.

SnappyBee then calls VirtualProtect to set the decrypted memory region as Read + Execute, and subsequently executes the code at the memory pointer. This is clearly where the unpacked code containing the next stage will be placed.

Unpacking the malware

Understanding how the unpacking routine works is the first step. The next step is obtaining the actual code, which cannot be achieved through static analysis alone.

There are two viable methods to retrieve the next stage. The first method is implementing the unpacking routine from scratch in a language like Python and running it against the data file.

This is straightforward in this case, as the unpacking routine in relatively simple and would not require much effort to re-implement. However, many unpacking routines are far more complex, which leads to the second method: allowing the malware to unpack itself by debugging it and then capturing the result. This is the approach many analysts take to unpacking, and the following will document this method to unpack SnappyBee.

As SnappyBee is 32-bit Windows malware, debugging can be performed using x86dbg in a Windows sandbox environment to debug SnappyBee. It is essential this sandbox is configured correctly, because any mistake during debugging could result in executing malicious code, which could have serious consequences.

Before debugging, it is necessary to disable the DYNAMIC_BASE flag on the DLL using a tool such as setdllcharacteristics. This will stop ASLR from randomizing the memory addresses each time the malware runs and ensures that it matches the addresses observed during static analysis.

The first place to set a breakpoint is DllMain, as this is the start of the malicious code and the logical place to pause before proceeding. Using IDA, the functions address can be determined; in this case, it is at offset 10002DB0. This can be used in the Goto (CTRL+G) dialog to jump to the offset and place a breakpoint. Note that the “Run to user code” button may need to be pressed if the DLL has not yet been loaded by x32dbg, as it spawns a small process to load the DLL as DLLs cannot be executed directly.

The program can then run until the breakpoint, at which point the program will pause and code recognizable from static analysis can be observed.

Figure 5: The x32dbg dissassembly listing forDllMain.

In the previous section, this function was noted as responsible for setting up a hook, and in the disassembly listing the hook address can be seen being loaded at offset 10002E1C. It is not necessary to go through the whole hooking process, because only the function that gets hooked in needs to be run. This function will not be naturally invoked as the DLL is being loaded directly rather than via sideloading as it expects. To work around this, the Extended Instruction Pointer (EIP) register can be manipulated to point to the start of the hook function instead, which will cause it to run instead of the DllMain function.

To update EIP, the CRTL+G dialog can again be used to jump to the hook function address (10002B50), and then the EIP register can be set to this address by right clicking the first instruction and selecting “Set EIP here”. This will make the hook function code run next.

Figure 6: The start of the hookedin-in function

Once in this function, there are a few addresses where breakpoints should be set in order to inspect the state of the program at critical points in the unpacking process. These are:

-              10002C93, which allocates the memory for the data file and final code

-              10002D2D, which decrypts the memory

-              10002D81, which runs the unpacked code

Setting these can be done by pressing the dot next to the instruction listing, or via the CTRL+G Goto menu.

At the first breakpoint, the call to VirtualAlloc will be executed. The function returns the memory address of the created memory region, which is stored in the EAX register. In this case, the region was allocated at address 00700000.

Figure 7: The result of the VirtualAlloc call.

It is possible to right click the address and press “Follow in dump” to pin the contents of the memory to the lower pane, which makes it easy to monitor the region as the unpacking process continues.

Figure 8: The allocated memory region shown in x32dbg’s dump.

Single-stepping through the application from this point eventually reaches the call to ReadFile, which loads the file into the memory region.

Figure 9: The allocated memory region after the file is read into it, showing high entropy data.

The program can then be allowed to run until the next breakpoint, which after single-stepping will execute the call to mbedtls_arc4_crypt to decrypt the memory. At this point, the data in the dump will have changed.

Figure 10: The same memory region after the decryption is run, showing lower entropy data.

Right-clicking in the dump and selecting "Disassembly” will disassemble the data. This yields valid shell code, indicating that the unpacking succeeded, whereas corrupt or random data would be expected if the unpacking had failed.

Figure 11: The disassembly view of the allocated memory.

Right-clicking and selecting “Follow in memory map” will show the memory allocation under the memory map view. Right-clicking this then provides an option to dump the entire memory block to file.

Figure 12: Saving the allocated memory region.

This dump can then be opened in IDA, enabling further static analysis of the shellcode. Reviewing the shellcode, it becomes clear that it performs another layer of unpacking.

As the debugger is already running, the sample can be allowed to execute up to the final breakpoint that was set on the call to the unpacked shellcode. Stepping into this call will then allow debugging of the new shellcode.

The simplest way to proceed is to single-step through the code, pausing on each call instruction to consider its purpose. Eventually, a call instruction that points to one of the memory regions that were assigned will be reached, which will contain the next layer of unpacked code. Using the same disassembly technique as before, it can be confirmed that this is more unpacked shellcode.

Figure 13: The unpacked shellcode’s call to RDI, which points to more unpacked shellcode. Note this screenshot depicts the 64-bit variant of SnappyBee instead of 32-bit, however the theory is the same.

Once again, this can be dumped out and analyzed further in IDA. In this case, it is the final payload used by the SnappyBee malware.

Conclusion

Unpacking remains one of the most common anti-analysis techniques and is a feature of most sophisticated malware from threat groups. This technique of in-memory decryption reduces the forensic “surface area” of the malware, helping it to evade detection from anti-malware solutions. This blog walks through one such example and provides practical knowledge on how to unpack malware for deeper analysis.

In addition, this blog has detailed several other techniques used by threat actors to evade analysis, such as DLL sideloading to execute code without arising suspicion, dynamic API resolving to bypass static heuristics, and multiple nested stages to make analysis challenging.

Malware such as SnappyBee demonstrates a continued shift towards highly modular and low-friction malware toolkits that can be reused across many intrusions and campaigns. It remains vital for security teams  to maintain the ability to combat the techniques seen in these toolkits when responding to infections.

While the technical details of these techniques are primarily important to analysts, the outcomes of this work directly affect how a Security Operations Centre (SOC) operates at scale. Without the technical capability to reliably unpack and observe these samples, organizations are forced to respond without the full picture.

The techniques demonstrated here help close that gap. This enables security teams to reduce dwell time by understanding the exact mechanisms of a sample earlier, improve detection quality with behavior-based indicators rather than relying on hash-based detections, and increase confidence in response decisions when determining impact.

Credit to Nathaniel Bill (Malware Research Engineer)
Edited by Ryan Traill (Analyst Content Lead)

Indicators of Compromise (IoCs)

SnappyBee Loader 1 - 25b9fdef3061c7dfea744830774ca0e289dba7c14be85f0d4695d382763b409b

SnappyBee Loader 2 - b2b617e62353a672626c13cc7ad81b27f23f91282aad7a3a0db471d84852a9ac          

SnappyBee Payload - 1a38303fb392ccc5a88d236b4f97ed404a89c1617f34b96ed826e7bb7257e296

References

[1] https://www.trendmicro.com/en_gb/research/24/k/earth-estries.html

[2] https://www.darktrace.com/blog/salty-much-darktraces-view-on-a-recent-salt-typhoon-intrusion

[3] https://learn.microsoft.com/en-us/windows/win32/dlls/dllmain#parameters

[4] https://mbed-tls.readthedocs.io/projects/api/en/v2.28.4/api/file/arc4_8h/#_CPPv418mbedtls_arc4_cryptP20mbedtls_arc4_context6size_tPKhPh

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
Nathaniel Bill
Malware Research Engineer

More in this series

No items found.

Blog

/

Network

/

August 7, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

Default blog imageDefault blog image

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.

Continue reading
About the author
Adam Stevens
Senior Director of Product | Darktrace

Blog

/

AI

/

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.

Continue reading
About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
Elevate your network security with Darktrace AI