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July 27, 2022

Self-Learning AI for Zero-Day and N-Day Attack Defense

Explore the differences between zero-day and n-day attacks on different customer servers to learn how Darktrace detects and prevents cyber threats effectively.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Lewis Morgan
Cyber Analyst
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27
Jul 2022

Key Terms:

Zero-day | A recently discovered security vulnerability in computer software that has no currently available fix or patch. Its name come from the reality that vendors have “zero days” to act and respond.

N-day | A vulnerability that emerges in computer software in which a vendor is aware and may have already issued (or are currently working on) a patch or fix. Active exploits often already exist and await abuse by nefarious actors.

Traditional security solutions often apply signature-based-detection when identifying cyber threats, helping to defend against legacy attacks but consequently missing novel ones. Therefore, security teams often lend a lot of focus to ensuring that the risk of zero-day vulnerabilities is reduced [1]. As explored in this blog, however, organizations can face just as much of a risk from n-day attacks, since they invite the most attention from malicious actors [2]. This is due in part to the reduced complexity, cost and time invested in researching and finding new exploits compared with that found when attackers exploit zero-days. 

This blog will examine both a zero-day and n-day attack that two different Darktrace customers faced in the fall of 2021. This will include the activity Darktrace detected, along with the steps taken by Darktrace/Network to intervene. It will then compare the incidents, discuss the possible dangers of third-party integrations, and assess the deprecation of legacy security tools.

Revisiting zero-day attacks 

Zero-days are among the greatest concerns security teams face in the era of modern technology and networking. Defending critical systems from zero-day compromises is a task most legacy security solutions are often unable to handle. Due to the complexity of uncovering new security flaws and developing elaborate code that can exploit them, these attacks are often carried out by funded or experienced groups such as nation-state actors and APTs. One of history’s most prolific zero-days, ‘Stuxnet’, sent security teams worldwide into a global panic in 2010. This involved a widespread attack on Iranian nuclear infrastructure and was widely accepted to be a result of nation-state actors [3]. The Stuxnet worm took advantage of four zero-day exploits, compromising over 200,000 devices and physically damaging around 10% of the 9,000 critical centrifuges at the Natanz nuclear site. 

More recently, 2021 saw the emergence of several critical zero-day vulnerabilities within SonicWall’s product suite [4]. SonicWall is a security hardware manufacturer that provides hardware firewall devices, unified threat management, VPN gateways and network security solutions. Some of these vulnerabilities lie within their Secure Mobile Access (SMA) 100 series (for example, CVE-2019-7481, CVE-2021-20016 and CVE-2021-20038 to name a few). These directly affected VPN devices and often allowed attackers easy remote access to company devices. CVE-2021-20016 in particular incorporates an SQL-Injection vulnerability within SonicWall’s SSL VPN SMA 100 product line [5]. If exploited, this defect would allow an unauthenticated remote attacker to perform their own malicious SQL query in order to access usernames, passwords and other session related information. 

The N-day underdog

The shadow cast by zero-day attacks often shrouds that of n-day attacks. N-days, however, often pose an equal - if not greater - risk to the majority of organizations, particularly those in industrial sectors. Since these vulnerabilities have fixes available, all of the hard work around research is already done; malicious actors only need to view proof of concepts (POCs) or, if proficient in coding, reverse-engineer software to reveal code-changes (binary diffing) in order to exploit these security flaws in the wild. These vulnerabilities are typically attributed to opportunistic hackers and script-kiddies, where little research or heavy lifting is required.  

August 2021 gave rise to a critical vulnerability in Atlassian Confluence servers, namely CVE-2021-26084 [6]. Confluence is a widely used collaboration wiki tool and knowledge-sharing platform. As introduced and discussed a few months ago in a previous Darktrace blog (Explore Internet-Facing System Vulnerabilities), this vulnerability allows attackers to remotely execute code on internet-facing servers after exploiting injection vulnerabilities in Object-Graph Navigation Language (OGNL). Whilst Confluence had patches and fixes available to users, attackers still jumped on this opportunity and began scanning the internet for signs of critical devices serving this outdated software [7]. Once identified, they would  exploit the vulnerability, often installing crypto mining software onto the device. More recently, Darktrace explored a new vulnerability (CVE-2022-26134), disclosed midway through 2022, that affected Confluence servers and data centers using similar techniques to that found in CVE-2021-26084 [8]. 

SonicWall in the wild – 1. Zero-day attack

At the beginning of August 2021, Darktrace prevented an attack from taking place within a European automotive customer’s environment (Figure 1). The attack targeted a vulnerable internet-facing SonicWall VPN server, and while the attacker’s motive remains unclear, similar historic events suggest that they intended to perform ransomware encryption or data exfiltration. 

Figure 1: Timeline of the SonicWall attack 

Darktrace was unable to confirm the definite tactics, techniques and procedures (TTPs) used by the attacker to compromise the customer’s environment, as the device was compromised before Darktrace installation and coverage. However, from looking at recently disclosed SonicWall VPN vulnerabilities and patterns of behaviour, it is likely CVE-2021-20016 played a part. At some point after this initial infection, it is also believed the device was able to move laterally to a domain controller (DC) using administrative credentials; it was this server that then initiated the anomalous activity that Darktrace detected and alerted on. 

On August 5th 2021 , Darktrace observed this compromised domain controller engaging in unusual ICMP scanning - a protocol used to discover active devices within an environment and create a map of an organization’s network topology. Shortly after, the infected server began scanning devices for open RDP ports and enumerating SMB shares using unorthodox methods. SMB delete and HTTP requests (over port 445 and 80 respectively) were made for files named delete.me in the root directory of numerous network shares using the user agent Microsoft WebDAV. However, no such files appeared to exist within the environment. This may have been the result of an attacker probing devices in the network in an effort to see their responses and gather information on properties and vulnerabilities they could later exploit. 

Soon the infected DC began establishing RDP tunnels back to the VPN server and making requests to an internal DNS server for multiple endpoints relating to exploit kits, likely in an effort to strengthen the attacker’s foothold within the environment. Some of the endpoints requested relate to:

-       EternalBlue vulnerability 

-       Petit Potam NTLM hash attack tool

-       Unusual GitHub repositories

-       Unusual Python repositories  

The DC made outgoing NTLM requests to other internal devices, implying the successful installation of Petit Potam exploitation tools. The server then began performing NTLM reconnaissance, making over 1,000 successful logins under ‘Administrator’ to several other internal devices. Around the same time, the device was also seen making anonymous SMBv1 logins to numerous internal devices, (possibly symptomatic of the attacker probing machines for EternalBlue vulnerabilities). 

Interestingly, the device also made numerous failed authentication attempts using a spoofed credential for one of the organization’s security managers. This was likely in an attempt to hide themselves using ‘Living off the Land’ (LotL) techniques. However, whilst the attacker clearly did their research on the company, they failed to acknowledge the typical naming convention used for credentials within the environment. This ultimately backfired and made the compromise more obvious and unusual. 

In the morning of the following day, the initially compromised VPN server began conducting further reconnaissance, engaging in similar activity to that observed by the domain controller. Until now, the customer had set Darktrace RESPOND to run in human confirmation mode, meaning interventions were not made autonomously but required confirmation by a member of the internal security team. However, thanks to Proactive Threat Notifications (PTNs) delivered by Darktrace’s dedicated SOC team, the customer was made immediately aware of this unusual behaviour, allowing them to apply manual Darktrace RESPOND blocks to all outgoing connections (Figure 2). This gave the security team enough time to respond and remediate before serious damage could be done.

Figure 2: Darktrace RESPOND model breach showing the manually applied “Quarantine Device” action taken against the compromised VPN server. This screenshot displays the UI from Darktrace version 5.1

Confluence in the wild – 2. N-day attack

Towards the end of 2021, Darktrace saw a European broadcasting customer leave an Atlassian Confluence internet-facing server unpatched and vulnerable to crypto-mining malware using CVE-2021-26084. Thanks to Darktrace, this attack was entirely immobilized within only a few hours of the initial infection, protecting the organization from damage (Figure 3). 

Figure 3: Timeline of the Confluence attack

On midday on September 1st 2021, an unpatched Confluence server was seen receiving SSL connections over port 443 from a suspicious new endpoint, 178.238.226[.]127.  The connections were encrypted, meaning Darktrace was unable to view the contents and ascertain what requests were being made. However, with the disclosure of CVE-2021-26084 just 7 days prior to this activity, it is likely that the TTPs used involved injecting OGNL expressions to Confluence server memory; allowing the attacker to remotely execute code on the vulnerable server.

Immediately after successful exploitation of the Confluence server, the infected device was observed making outgoing HTTP GET requests to several external endpoints using a new user agent (curl/7.61.1). Curl was used to silently download and configure multiple suspicious files relating to XMRig cryptocurrency miner, including ld.sh, XMRig and config.json. Subsequent outgoing connections were then made to europe.randomx-hub.miningpoolhub[.]com · 172.105.210[.]117 using the JSON-RPC protocol, seen alongside the mining credential maillocal.confluence (Figure 4). Only 3 seconds after initial compromise, the infected device began attempting to mine cryptocurrency using the Minergate protocol but was instantly and autonomously blocked by Darktrace RESPOND. This prevented the server from abusing system resources and generating profits for the attacker.

Figure 4: A graph showing the frequency of external connections using the JSON-RPC protocol made by the breach device over a 48-hour window. The orange-red dots represent models that breached as a result of this activity, demonstrating the “waterfall” effect commonly seen when a device suffers a compromise. This screenshot displays the UI from Darktrace version 5.1

In the afternoon, the malware persisted with its infection. The compromised server began making successive HTTP GET requests to a new rare endpoint 195.19.192[.]28 using the same curl user agent (Figures 5 & 6). These requests were for executable and dynamic library files associated with Kinsing malware (but fortunately were also blocked by Darktrace RESPOND). Kinsing is a malware strain found in numerous attack campaigns which is often associated with crypto-jacking, and has appeared in previous Darktrace blogs [9].

Figure 5: Cyber AI Analyst summarising the unusual download of Kinsing software using the new curl user agent. This screenshot displays the UI from Darktrace version 5.1

The attacker then began making HTTP POST requests to an IP 185.154.53[.]140, using the same curl user agent; likely a method for the attacker to maintain persistence within the network and establish a foothold using its C2 infrastructure. The Confluence server was then again seen attempting to mine cryptocurrency using the Minergate protocol. It made outgoing JSON-RPC connections to a different new endpoint, 45.129.2[.]107, using the following mining credential: ‘42J8CF9sQoP9pMbvtcLgTxdA2KN4ZMUVWJk6HJDWzixDLmU2Ar47PUNS5XHv4Kmfdh8aA9fbZmKHwfmFo8Wup8YtS5Kdqh2’. This was once again blocked by Darktrace RESPOND (Figure 7). 

Figure 6: VirusTotal showing the unusualness of one of these external IPs [10]
Figure 7: Log data showing the action taken by Darktrace RESPOND in response to the device breaching the “Crypto Currency Mining Activity” model. This screenshot displays the UI from Darktrace version 5.1

The final activity seen from this device involved the download of additional shell scripts over HTTP associated with Kinsing, namely spre.sh and unk.sh, from 194.38.20[.]199 and 195.3.146[.]118 respectively (Figure 8). A new user agent (Wget/1.19.5 (linux-gnu)) was used when connecting to the latter endpoint, which also began concurrently initiating repeated connections indicative of C2 beaconing. These scripts help to spread the Kinsing malware laterally within the environment and may have been the attacker's last ditch efforts at furthering their compromise before Darktrace RESPOND blocked all connections from the infected Confluence server [11]. With Darktrace RESPOND's successful actions, the customer’s security team were then able to perform their own response and remediation. 

Figure 8: Cyber AI Analyst revealing the last ditch efforts made by the threat actor to download further malicious software. This screenshot displays the UI from Darktrace version 5.1

Darktrace Coverage: N- vs Zero-days

In the SonicWall case the attacker was unable to achieve their actions on objectives (thanks to Darktrace's intervention). However, this incident displayed tactics of a more stealthy and sophisticated attacker - they had an exploited machine but waited for the right moment to execute their malicious code and initiate a full compromise. Due to the lack of visibility over attacker motive, it is difficult to deduce what type of actor led to this intrusion. However, with the disclosure of a zero-day vulnerability (CVE-2021-20016) not long before this attack, along with a seemingly dormant initially compromised device, it is highly possible that it was carried out by a sophisticated cyber criminal or gang. 

On the other hand, the Confluence case engaged in a slightly more noisy approach; it dropped crypto mining malware on vulnerable devices in the hope that the target’s security team did not maintain visibility over their network or would merely turn a blind eye. The files downloaded and credentials observed alongside the mining activity heavily imply the use of Kinsing malware [11]. Since this vulnerability (CVE-2021-26084) emerged as an n-day attack with likely easily accessible POCs, as well as there being a lack of LotL techniques and the motive being long term monetary gain, it is possible this attack was conducted by a less sophisticated or amateur actor (script-kiddie); one that opportunistically exploits known vulnerabilities in internet-facing devices in order to make a quick profit [12].

Whilst Darktrace RESPOND was enabled in human confirmation mode only during the start of the SonicWall attack, Darktrace’s Cyber AI Analyst still offered invaluable insight into the unusual activity associated with the infected machines during both the Confluence and SonicWall compromises. SOC analysts were able to see these uncharacteristic behaviours and escalate the incident through Darktrace’s PTN and ATE services. Analysts then worked through these tickets with the customers, providing support and guidance and, in the SonicWall case, quickly helping to configure Darktrace RESPOND. In both scenarios, Darktrace RESPOND was able to block abnormal connections and enforce a device’s pattern of life, affording the security team enough time to isolate the infected machines and prevent further threats such as ransomware detonation or data exfiltration. 

Concluding thoughts and dangers of third-party integrations 

Organizations with internet-facing devices will inevitably suffer opportunistic zero-day and n-day attacks. While little can be done to remove the risk of zero-days entirely, ensuring that organizations keep their systems up to date will at the very least help prevent opportunistic and script-kiddies from exploiting n-day vulnerabilities.  

However, it is often not always possible for organizations to keep their systems up to date, especially for those who require continuous availability. This may also pose issues for organizations that rely on, and put their trust in, third party integrations such as those explored in this blog (Confluence and SonicWall), as enforcing secure software is almost entirely out of their hands. Moreover, with the rising prevalence of remote working, it is essential now more than ever that organizations ensure their VPN devices are shielded from external threats, guidance on which has been released by the NSA/CISA [13].

These two case studies have shown that whilst organizations can configure their networks and firewalls to help identify known indicators of compromise (IoC), this ‘rearview mirror’ approach will not account for, or protect against, any new and undisclosed IoCs. With the aid of Self-Learning AI and anomaly detection, Darktrace can detect the slightest deviation from a device’s normal pattern of life and respond autonomously without the need for rules and signatures. This allows for the disruption and prevention of known and novel attacks before irreparable damage is caused- reassuring security teams that their digital estates are secure. 

Thanks to Paul Jennings for his contributions to this blog.

Appendices: SonicWall (Zero-day)

Darktrace model detections

·      AIA / Suspicious Chain of Administrative Credentials

·      Anomalous Connection / Active Remote Desktop Tunnel

·      Anomalous Connection / SMB Enumeration

·      Anomalous Connection / Unusual Internal Remote Desktop

·      Compliance / High Priority Compliance Model Breach

·      Compliance / Outgoing NTLM Request from DC

·      Device / Anomalous RDP Followed By Multiple Model Breaches

·      Device / Anomalous SMB Followed By Multiple Model Breaches

·      Device / ICMP Address Scan

·      Device / Large Number of Model Breaches

·      Device / Large Number of Model Breaches from Critical Network Device

·      Device / Multiple Lateral Movement Model Breaches (PTN/Enhanced Monitoring model)

·      Device / Network Scan

·      Device / Possible SMB/NTLM Reconnaissance

·      Device / RDP Scan

·      Device / Reverse DNS Sweep

·      Device / SMB Session Bruteforce

·      Device / Suspicious Network Scan Activity (PTN/Enhanced Monitoring model)

·      Unusual Activity / Possible RPC Recon Activity

Darktrace RESPOND (Antigena) actions (as displayed in example)

·      Antigena / Network / Manual / Quarantine Device

MITRE ATT&CK Techniques Observed
IoCs

Appendices: Confluence (N-day)

Darktrace model detections

·      Anomalous Connection / New User Agent to IP Without Hostname

·      Anomalous Connection / Posting HTTP to IP Without Hostname

·      Anomalous File / EXE from Rare External Location

·      Anomalous File / Script from Rare Location

·      Compliance / Crypto Currency Mining Activity

·      Compromise / High Priority Crypto Currency Mining (PTN/Enhanced Monitoring model)

·      Device / Initial Breach Chain Compromise (PTN/Enhanced Monitoring model)

·      Device / Internet Facing Device with High Priority Alert

·      Device / New User Agent

Darktrace RESPOND (Antigena) actions (displayed in example)

·      Antigena / Network / Compliance / Antigena Crypto Currency Mining Block

·      Antigena / Network / External Threat / Antigena File then New Outbound Block

·      Antigena / Network / External Threat / Antigena Suspicious Activity Block

·      Antigena / Network / External Threat / Antigena Suspicious File Block

·      Antigena / Network / Significant Anomaly / Antigena Block Enhanced Monitoring

MITRE ATT&CK Techniques Observed
IOCs

References:

[1] https://securitybrief.asia/story/why-preventing-zero-day-attacks-is-crucial-for-businesses

[2] https://electricenergyonline.com/energy/magazine/1150/article/Security-Sessions-More-Dangerous-Than-Zero-Days-The-N-Day-Threat.htm

[3] https://www.wired.com/2014/11/countdown-to-zero-day-stuxnet/

[4] https://cve.mitre.org/cgi-bin/cvekey.cgi?keyword=SonicWall+2021 

[5] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-20016

[6] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-26084

[7] https://www.zdnet.com/article/us-cybercom-says-mass-exploitation-of-atlassian-confluence-vulnerability-ongoing-and-expected-to-accelerate/

[8] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2022-26134

[9] https://attack.mitre.org/software/S0599/

[10] https://www.virustotal.com/gui/ip-address/195.19.192.28/detection 

[11] https://sysdig.com/blog/zoom-into-kinsing-kdevtmpfsi/

[12] https://github.com/alt3kx/CVE-2021-26084_PoC

[13] https://www.nsa.gov/Press-Room/Press-Releases-Statements/Press-Release-View/Article/2791320/nsa-cisa-release-guidance-on-selecting-and-hardening-remote-access-vpns/

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
Lewis Morgan
Cyber Analyst

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August 7, 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 | Darktrace

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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
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