Blog
/
Network
/
October 27, 2022

Strategies to Prolong Quantum Ransomware Attacks

Learn more about how Darktrace combats Quantum Ransomware changing strategy for cyberattacks. Explore the power of AI-driven network cyber security!
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
Nicole Wong
Cyber Security Analyst
Default blog image
27
Oct 2022

Within science and engineering, the word ‘quantum’ may spark associations with speed and capability, referencing a superior computer that can perform tasks a classical computer cannot. In cyber security, some may recognize ‘quantum’ in relation to cryptography or, more recently, as the name of a new ransomware group, which achieved network-wide encryption a mere four hours after an initial infection.   

Although this group now has a reputation for carrying out fast and efficient attacks, speed is not their only tactic. In August 2022, Darktrace detected a Quantum Ransomware incident where attackers remained in the victim’s network for almost a month after the initial signs of infection, before detonating ransomware. This was a stark difference to previously reported attacks, demonstrating that as motives change, so do threat actors’ strategies. 

The Quantum Group

Quantum was first identified in August 2021 as the latest of several rebrands of MountLocker ransomware [1]. As part of this rebrand, the extension ‘.quantum’ is appended to filenames that are encrypted and the associated ransom notes are named ‘README_TO_DECRYPT.html’ [2].  

From April 2022, media coverage of this group has increased following a DFIR report detailing an attack that progressed from initial access to domain-wide ransomware within four hours [3]. To put this into perspective, the global median dwell time for ransomware in 2020 and 2021 is 5 days [4]. In the case of Quantum, threat actors gained direct keyboard access to devices merely 2 hours after initial infection. The ransomware was staged on the domain controller around an hour and a half later, and executed 12 minutes after that.   

Quantum’s behaviour bears similarities to other groups, possibly due to their history and recruitment. Several members of the disbanded Conti ransomware group are reported to have joined the Quantum and BumbleBee operations. Security researchers have also identified similarities in the payloads and C2 infrastructure used by these groups [5 & 6].  Notably, these are the IcedID initial payload and Cobalt Strike C2 beacon used in this attack. Darktrace has also observed and prevented IcedID and Cobalt Strike activity from BumbleBee across several customer environments.

The Attack

From 11th July 2022, a device suspected to be patient zero made repeated DNS queries for external hosts that appear to be associated with IcedID C2 traffic [7 & 8]. In several reported cases [9 & 10], this banking trojan is delivered through a phishing email containing a malicious attachment that loads an IcedID DLL. As Darktrace was not deployed in the prospect’s email environment, there was no visibility of the initial access vector, however an example of a phishing campaign containing this payload is presented below. It is also possible that the device was already infected prior to joining the network. 

Figure 1- An example phishing email used to distribute IcedID. If configured, Darktrace/Email would be able to detect that the email was sent from an anomalous sender, was part of a fake reply chain, and had a suspicious attachment containing compressed content of unusual mime type [11].    

 

Figure 2- The DNS queries to endpoints associated with IcedID C2 servers, taken from the infected device’s event log.  Additional DNS queries made to other IcedID C2 servers are in the list of IOCs in the appendices.  The repeated DNS queries are indicative of beaconing.


It was not until 22nd July that activity was seen which indicated the attack had progressed to the next stage of the kill chain. This contrasts the previously seen attacks where the progression to Cobalt Strike C2 beaconing and reconnaissance and lateral movement occurred within 2 hours of the initial infection [12 & 13]. In this case, patient zero initiated numerous unusual connections to other internal devices using a compromised account, connections that were indicative of reconnaissance using built-in Windows utilities:

·      DNS queries for hostnames in the network

·      SMB writes to IPC$ shares of those hostnames queried, binding to the srvsvc named pipe to enumerate things such as SMB shares and services on a device, client access permissions on network shares and users logged in to a remote session

·      DCE-RPC connections to the endpoint mapper service, which enables identification of the ports assigned to a particular RPC service

These connections were initiated using an existing credential on the device and just like the dwelling time, differed from previously reported Quantum group attacks where discovery actions were spawned and performed automatically by the IcedID process [14]. Figure 3 depicts how Darktrace detected that this activity deviated from the device’s normal behaviour.  

Figure 3- This figure displays the spike in active internal connections initiated by patient zero. The coloured dots represent the Darktrace models that were breached, detecting this unusual reconnaissance and lateral movement activity.

Four days later, on the 26th of July, patient zero performed SMB writes of DLL and MSI executables to the C$ shares of internal devices including domain controllers, using a privileged credential not previously seen on the patient zero device. The deviation from normal behaviour that this represents is also displayed in Figure 3. Throughout this activity, patient zero made DNS queries for the external Cobalt Strike C2 server shown in Figure 4. Cobalt Strike has often been seen as a secondary payload delivered via IcedID, due to IcedID’s ability to evade detection and deploy large scale campaigns [15]. It is likely that reconnaissance and lateral movement was performed under instructions received by the Cobalt Strike C2 server.   

Figure 4- This figure is taken from Darktrace’s Advanced Search interface, showing a DNS query for a Cobalt Strike C2 server occurring during SMB writes of .dll files and DCE-RPC requests to the epmapper service, demonstrating reconnaissance and lateral movement.


The SMB writes to domain controllers and usage of a new account suggests that by this stage, the attacker had achieved domain dominance. The attacker also appeared to have had hands-on access to the network via a console; the repetition of the paths ‘programdata\v1.dll’ and ‘ProgramData\v1.dll’, in lower and title case respectively, suggests they were entered manually.  

These DLL files likely contained a copy of the malware that injects into legitimate processes such as winlogon, to perform commands that call out to C2 servers [16]. Shortly after the file transfers, the affected domain controllers were also seen beaconing to external endpoints (‘sezijiru[.]com’ and ‘gedabuyisi[.]com’) that OSINT tools have associated with these DLL files [17 & 18]. Moreover, these SSL connections were made using a default client fingerprint for Cobalt Strike [19], which is consistent with the initial delivery method. To illustrate the beaconing nature of these connections, Figure 5 displays the 4.3 million daily SSL connections to one of the C2 servers during the attack. The 100,000 most recent connections were initiated by 11 unique source IP addresses alone.

Figure 5- The Advanced Search interface, querying for external SSL connections from devices in the network to an external host that appears to be a Cobalt Strike C2 server. 4.3 million connections were made over 8 days, even after the ransomware was eventually detonated on 2022-08-03.


Shortly after the writes, the attack progressed to the penultimate stage. The next day, on the 27th of July, the attackers moved to achieve their first objective: data exfiltration. Data exfiltration is not always performed by the Quantum ransomware gang. Researchers have noted discrepancies between claims of data theft made in their ransom notes versus the lack of data seen leaving the network, although this may have been missed due to covert exfiltration via a Cobalt Strike beacon [20]. 

In contrast, this attack displayed several gigabytes of data leaving internal devices including servers that had previously beaconed to Cobalt Strike C2 servers. This data was transferred overtly via FTP, however the attacker still attempted to conceal the activity using ephemeral ports (FTP in EPSV mode). FTP is an effective method for attackers to exfiltrate large files as it is easy to use, organizations often neglect to monitor outbound usage, and it can be shipped through ports that will not be blocked by traditional firewalls [21].   

Figure 6 displays an example of the FTP data transfer to attacker-controlled infrastructure, in which the destination share appears structured to identify the organization that the data was stolen from, suggesting there may be other victim organizations’ data stored. This suggests that data exfiltration was an intended outcome of this attack. 

Figure 6- This figure is from Darktrace’s Advanced Search interface, displaying some of the data transferred from an internal device to the attacker’s FTP server.

 
Data was continuously exfiltrated until a week later when the final stage of the attack was achieved and Quantum ransomware was detonated. Darktrace detected the following unusual SMB activity initiated from the attacker-created account that is a hallmark for ransomware (see Figure 7 for example log):

·      Symmetric SMB Read to Write ratio, indicative of active encryption

·      Sustained MIME type conversion of files, with the extension ‘.quantum’ appended to filenames

·      SMB writes of a ransom note ‘README_TO_DECRYPT.html’ (see Figure 8 for an example note)

Figure 7- The Model Breach Event Log for a device that had files encrypted by Quantum ransomware, showing the reads and writes of files with ‘.quantum’ appended to encrypted files, and an HTML ransom note left where the files were encrypted.

 

Figure 8- An example of the ransom note left by the Quantum gang, this one is taken from open-sources [22].


The example in Figure 8 mentions that the attacker also possessed large volumes of victim data.  It is likely that the gigabytes of data exfiltrated over FTP were leveraged as blackmail to further extort the victim organization for payment.  

Darktrace Coverage

 

Figure 9- Timeline of Quantum ransomware incident


If Darktrace/Email was deployed in the prospect’s environment, the initial payload (if delivered through a phishing email) could have been detected and held from the recipient’s inbox. Although DETECT identified anomalous network behaviour at each stage of the attack, since the incident occurred during a trial phase where Darktrace could only detect but not respond, the attack was able to progress through the kill chain. If RESPOND/Network had been configured in the targeted environment, the unusual connections observed during the initial access, C2, reconnaissance and lateral movement stages of the attack could have been blocked. This would have prevented the attackers from delivering the later stage payloads and eventual ransomware into the target network.

It is often thought that a properly implemented backup strategy is sufficient defense against ransomware [23], however as discussed in a previous Darktrace blog, the increasing frequency of double extortion attacks in a world where ‘data is the new oil’ demonstrates that backups alone are not a mitigation for the risk of a ransomware attack [24]. Equally, the lack of preventive defenses in the target’s environment enabled the attacker’s riskier decision to dwell in the network for longer and allowed them to optimize their potential reward. 

Recent crackdowns from law enforcement on ransomware groups have shifted these groups’ approaches to aim for a balance between low risk and significant financial rewards [25]. However, given the Quantum gang only have a 5% market share in Q2 2022, compared to the 13.2% held by LockBit and 16.9% held by BlackCat [26], a riskier strategy may be favourable, as a longer dwell time and double extortion outcome offers a ‘belt and braces’ approach to maximizing the rewards from carrying out this attack. Alternatively, the gaps in-between the attack stages may imply that more than one player was involved in this attack, although this group has not been reported to operate a franchise model before [27]. Whether assisted by others or driving for a risk approach, it is clear that Quantum (like other actors) are continuing to adapt to ensure their financial success. They will continue to be successful until organizations dedicate themselves to ensuring that the proper data protection and network security measures are in place. 

Conclusion 

Ransomware has evolved over time and groups have merged and rebranded. However, this incident of Quantum ransomware demonstrates that regardless of the capability to execute a full attack within hours, prolonging an attack to optimize potential reward by leveraging double extortion tactics is sometimes still the preferred action. The pattern of network activity mirrors the techniques used in other Quantum attacks, however this incident lacked the continuous progression of the group’s attacks reported recently and may represent a change of motives during the process. Knowing that attacker motives can change reinforces the need for organizations to invest in preventative controls- an organization may already be too far down the line if it is executing its backup contingency plans. Darktrace DETECT/Network had visibility over both the early network-based indicators of compromise and the escalation to the later stages of this attack. Had Darktrace also been allowed to respond, this case of Quantum ransomware would also have had a very short dwell time, but a far better outcome for the victim.

Thanks to Steve Robinson for his contributions to this blog.

Appendices

References

[1] https://community.ibm.com/community/user/security/blogs/tristan-reed/2022/07/13/ibm-security-reaqta-vs-quantum-locker-ransomware

 

[2] https://www.bleepingcomputer.com/news/security/quantum-ransomware-seen-deployed-in-rapid-network-attacks/

 

[3], [12], [14], [16], [20] https://thedfirreport.com/2022/04/25/quantum-ransomware/

 

[4] https://www.mandiant.com/sites/default/files/2022-04/M-Trends%202022%20Executive%20Summary.pdf

 

[5] https://cyware.com/news/over-650-healthcare-organizations-affected-by-the-quantum-ransomware-attack-d0e776bb/

 

[6] https://www.kroll.com/en/insights/publications/cyber/bumblebee-loader-linked-conti-used-in-quantum-locker-attacks

 

[7] https://github.com/pan-unit42/tweets/blob/master/2022-06-28-IOCs-for-TA578-IcedID-Cobalt-Strike-and-DarkVNC.txt 

 

[8] https://github.com/stamparm/maltrail/blob/master/trails/static/malware/icedid.txt

 

[9], [15] https://www.cynet.com/blog/shelob-moonlight-spinning-a-larger-web-from-icedid-to-conti-a-trojan-and-ransomware-collaboration/

 

[10] https://www.microsoft.com/security/blog/2021/04/09/investigating-a-unique-form-of-email-delivery-for-icedid-malware/

 

[11] https://twitter.com/0xToxin/status/1564289244084011014

 

[13], [27] https://cybernews.com/security/quantum-ransomware-gang-fast-and-furious/

 

[17] https://www.virustotal.com/gui/domain/gedabuyisi.com/relations

 

[18] https://www.virustotal.com/gui/domain/sezijiru.com/relations.

 

[19] https://github.com/ByteSecLabs/ja3-ja3s-combo/blob/master/master-list.txt 

 

[21] https://www.darkreading.com/perimeter/ftp-hacking-on-the-rise

 

[22] https://www.pcrisk.com/removal-guides/23352-quantum-ransomware

 

[23] https://www.cohesity.com/resource-assets/tip-sheet/5-ways-ransomware-renders-backup-useless-tip-sheet-en.pdf

 

[24] https://www.forbes.com/sites/nishatalagala/2022/03/02/data-as-the-new-oil-is-not-enough-four-principles-for-avoiding-data-fires/ 

 

[25] https://www.bleepingcomputer.com/news/security/access-to-hacked-corporate-networks-still-strong-but-sales-fall/

 

[26] https://www.bleepingcomputer.com/news/security/ransom-payments-fall-as-fewer-victims-choose-to-pay-hackers/ 

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
Nicole Wong
Cyber Security Analyst

More in this series

No items found.

Blog

/

Network

/

August 6, 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. The defense must be too.

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

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

Blog

/

/

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