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August 3, 2026

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

Darktrace’s analysis of the first half of 2026 shows attackers increasingly exploiting trust rather than bypassing security controls. Identity compromise, supply-chain attacks, SaaS abuse, AI-enabled operations, and state-aligned activity demonstrate how trusted users, services, and infrastructure have become key attack paths. For defenders, context and behavioral analysis remain essential foundations of 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
Nathaniel Jones
SVP, Global Threat Intelligence
Written by
Emma Foulger
Global Threat Research Operations Lead
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03
Aug 2026

In early 2026, a React2Shell honeypot purpose-built by Darktrace analysts was compromised in less than two hours after deployment. That single data point captures the pace of the threat landscape in the first half of 2026, but speed tells only part of the story.

The shift over the past six months has moved away from traditional malware and vulnerability-centric attacks and toward the abuse of trusted identities, platforms, and infrastructure. Identities, Software-as-a-Service (SaaS) platforms, cloud entitlements, automation frameworks, and non-human identities have become the preferred attack paths as organizations adopt AI at scale.

Attackers are increasingly operating inside the relationships, services, and authenticated channels that defenders and users are conditioned to rely on, rather than breaking in from the outside.

What has changed since 2025?

In 2025, identity became the new perimeter as attackers increasingly bypassed traditional exploitation in favor of trusted accounts, SaaS platforms, and emerging AI-enabled tradecraft. The first half of 2026 marks the next stage of that evolution. Identity remains central, but the trust challenge now extends far beyond accounts to email authentication, cloud entitlements, software supply chains, AI gateways, remote administration tooling, and non-human identities.

Theme 2025 (Mid-Year / Annual) H1 2026
Identity Credentials remained the weak link; identity emerged as the new perimeter. Identity remains the entry point, but trust has become the new attack surface.
Cloud & SaaS SaaS-targeted ransomware continued to rise. Cloud and SaaS became the attacker's preferred operating environment.
AI Large Language Models (LLMs) were suspected of influencing phishing shifts. LLM-generated malware, compromised AI proxies, and the abuse of AI identities emerged.
Attack Surface Scale & Speed Exponential growth of Common Vulnerabilities and Exposures (CVEs), with public proof-of-concepts appearing faster. Cloud and AI adoption expanded the attack surface, while AI accelerated exploitation. One honeypot was compromised in under two hours.
Supply Chain Legitimate services were increasingly abused. Trusted maintainers and CI/CD workflows were weaponized.

Identity and email: trust signals under pressure

Email remains the most reliable route to a trusted identity, and the data shows attackers investing in quality over noise. In the first half of 2026, 67% of phishing emails passed DMARC. Authentication alone is no longer sufficient to stop most phishing attempts. VIP users were targeted in 25.8% of phishing, consistent with 2025's “over 25%” figure, but drifting upward throughout the period. Crucially, phishing sophistication continued to increase: 37% of phishing contained a high volume of text, up from 32% in the first half of 2025, while 39% featured novel social engineering techniques, suggesting attackers are further customizing to specific targets.

The most prevalent threats affecting Darktrace customers were also among the most identity-centric: information stealers, with dedicated StealC and AMOS campaigns running through the half-year. Their prevalence is, fundamentally, an identity story. Credentials harvested by infostealers often become the initial access vector for far higher-impact intrusions later in the attack chain. Crucially, the delivery method rarely requires exploitation of a technical weakness. ClickFix social engineering, which tricks users into running malicious code themselves, remained a common distribution route. One recent campaign impacted Darktrace customers across 17 countries, with the United States the most affected. The compromise did not begin with a software flaw, but with a trusted user taking a trusted action.

Supply chain: Trust weaponized at scale

March and April reinforced the same lesson: trust has become a supply-chain vulnerability. The Axios compromise abused trust in a widely used maintainer, while the Trivy campaign leveraged trusted CI/CD infrastructure, release artifacts, and container images to push malicious code through legitimate development workflows.

The clearest example was a February–March campaign in which devices downloaded malicious payloads while using Hola VPN, later linked to an issue within Hola's own delivery pipeline. Darktrace's Threat Research team identified associated activity through recurring anomalous behavior across multiple customers before a public advisory was released.

More recently, attackers abused legitimate blockchain infrastructure to distribute infostealers, including AMOS and Phexia. Popular tools like VPNs, often used by users with limited security resources, combined with legitimate command-and-control (C2) infrastructure enables attackers to reach a far wider victim base while frustrating defenders who cannot simply block the associated endpoints.

For defenders, the challenge is no longer identifying malicious infrastructure, but recognizing when trusted infrastructure begins behaving maliciously.

Cloud and SaaS: from target to terrain

Through May and June, activity involving device registration, cloud data theft, SaaS abuse, RDP expansion, and remote management tooling suggested that attackers increasingly view cloud and SaaS not simply as targets, but as their preferred operating environment.

In one Darktrace case a single compromised SaaS account triggered activity across email, SaaS, and network layers, including inbox rule changes, phishing propagation, and connections to suspicious infrastructure. None of these indicators were decisive in isolation, but together they revealed a clear intrusion. Increasingly, attackers do not need to bypass trust controls in these environments; they inherit them through compromised identities, delegated access, and legitimate administration tools. This is the natural progression of 2025's SaaS-targeted ransomware trend: the platforms on which businesses operate are increasingly the same platforms on which adversaries operate.

AI: accelerant, attack surface, and trusted but risky actor

If trust is the attack surface, AI is where that surface is expanding fastest. Across the Darktrace customer base, AI service connections per deployment rose 13% in the first half of 2026, surpassing 16 million connections, while the typical organization now interacts with seven different AI providers. AI is no longer at the edge of the enterprise; it is embedded in day-to-day business operations. That shift creates three distinct problems, all of which were observed by Darktrace in the first half of 2026.

1. AI as an attack multiplier

Darktrace identified AI-generated malware exploiting React2Shell, in which an attacker used an LLM to produce working exploit code and deploy it at scale. Similar activity is increasingly appearing across the wider threat landscape, suggesting that the barrier to effective offensive operations is collapsing. As demonstrated by the recent JadePuffer case, in which an agentic threat actor exploited a vulnerability in an internet-facing server before launching a fully automated ransomware attack, AI is accelerating the path from vulnerability disclosure to operational exploitation [1].

2. AI as an attack surface

The AI layer itself is now worth probing. At an automation technology manufacturer, a compromised LLM proxy was used as a steppingstone toward additional AI services; when that failed, the attacker pivoted to cryptomining. Darktrace’s Cyber AI Analyst pieced the intrusion together and Darktrace’s Managed Threat Detection service alerted the customer, containing it before it could progress further. The practitioner lesson is clear: treat AI gateways, proxies, and model endpoints as production cloud workloads because attackers already do.

3. AI as a trusted but potentially risky actor

Darktrace / SECURE AI observations suggest the most common real-world risk is quieter still: employees entering personal identifiable information (PII), tax records, identity documents, company financial data, HR records, and personal medical data into LLM prompts, alongside widespread shadow AI use and increased AI usage from mobile devices. Across nearly 280,000 prompts submitted by almost 28,000 users over 28 days, Darktrace identified that approximately 1% of these prompts (or 2,945 instances) contained sensitive data*.

*Prompt data was analyzed in aggregate and anonymized form to protect user privacy.

For defenders, the challenge is context: knowing when legitimate business use crosses into material risk without breaking privacy or user trust. As organizations increasingly trust AI systems to access, process, and share sensitive information at machine speed, AI must be secured and monitored alongside identities, applications, and cloud infrastructure.

Speed and geopolitics: faster operations, longer-term objectives

Several investigations in the first half of the year showed how quickly attackers operationalize newly disclosed vulnerabilities, validating exploitation through Out-of-Band Application Security Testing (OAST) infrastructure and trusted cloud services before patching cycles can be completed. React2Shell was compromised in two hours, while BeyondTrust exploitation followed in less than a day. Against this backdrop, state-aligned actors continue to prioritize long-term access, intelligence collection, and pre-positioning through legitimate services, cloud infrastructure, and trusted relationships. Operations linked to China, Russia, Iran, and the Democratic People’s Republic of Korea (DPRK) shared a common characteristic: a focus on persistence and strategic positioning rather than immediate disruption.

China: Darktrace observed Chinese-nexus actors prioritizing long-term access through trusted services, dynamic-link library (DLL) sideloading, and modular intrusion chains consistent with activity documented in Crimson Echo reporting and associated with Twill Typhoon tradecraft.

Iran: Darktrace's ZionSiphon investigation highlighted Iranian-linked interest in operational technology (OT) environments, blending espionage objectives with infrastructure disruption capabilities.

Russia: Darktrace investigations, alongside wider industry reporting, highlighted Russian reliance on trusted relationships and supply-chain targeting for long-term intelligence on Ukraine related support [2].

DPRK: Darktrace observed DPRK-linked activity combining rapid vulnerability weaponization with persistent access techniques, including Axios supply-chain compromise, React2Shell exploitation and stealthy macOS intrusions

While objectives differed across actors, the tradecraft was remarkably consistent: trusted services, legitimate infrastructure, and persistent access remained more valuable than immediate disruption.

The defender shift

Across identity compromise, supply-chain attacks, SaaS abuse, AI infrastructure targeting, and state-aligned operations, attackers increasingly succeed by operating through trusted systems rather than breaking through defensive controls. Trusted users, trusted software, trusted infrastructure, and increasingly trusted AI systems all became viable attack paths.

For defenders, the challenge is no longer simply determining whether an action is allowed; it is determining whether that action makes sense in its wider context. Authentication, reputation, and provenance remain important, but they are no longer sufficient on their own. As attackers increasingly operate within trusted systems, the strongest signal is often a behavioral deviation: identifying when trusted activity no longer aligns with expected behavior.

Credit to Nathaniel Jones (SVP, Global Threat Intelligence), Emma Foulger (Global Threat Research Operations Lead), Justin Torres (Senior Cyber Analyst), Daniel Levy (Threat Hunting Data Scientist)


Edited by Ryan Traill (Content Manager)

Appendix 1: Threat Research Methodology

Darktrace’s Threat Research team conducts extensive research across customer deployments to identify active threats, pinpoint key Indicators of Compromise (IoCs), and provide relevant threat intelligence. This research leverages Darktrace’s anomaly-based detection and involves thorough analysis and contextualization by the Threat Research team. Detected threats are promptly reported to the relevant customer security teams. When a customer has Darktrace’s Autonomous Response technology enabled, these threats are swiftly mitigated to prevent escalation.

Between January 1 and June 30, 2026, Darktrace investigated a wide range of cyber threats across its customer base. Many were identified as campaign-like activities targeting multiple customers, where clusters of similar tactics, techniques, and procedures (TTPs) and IoCs were seen affecting a significant number of customers within a short timeframe.

Statistics related to email are derived from aggregated Darktrace / EMAIL data across all cloud-hosted customer deployments between January 1 and June 30, 2026. Standard data-quality filtering was applied to exclude anomalous observations prior to aggregation. Regional statistics are based on relevant subsets of this dataset.

Appendix 2: Campaigns - Regional and Sector Trends

While the above broad themes defined the threat landscape over the last six months, campaign clustering across the Darktrace customer base revealed how they manifested differently across sectors, regions, and industries.

Darktrace’s Threat Research team investigates a range of threats affecting its customer base. Through this research, campaign-like clusters of activity have been identified, in which common tactics, techniques, and procedures (TTPs), as well as infrastructure, are observed impacting a significant number of customers within a short timeframe.

Sectors and industries are classified using the Standard Industrial Classification (SIC) system to ensure consistent categorization. While the sector and regional insights in this report reflect broader global trends, they are also influenced by the distribution of Darktrace's customer base. For example, Finance, Manufacturing, and Education are strongly represented among Darktrace customers, which may result in a higher number of observed cases in these sectors. This reflects customer distribution rather than necessarily indicating elevated sector-specific risk. Similarly, regional trends may be influenced by the geographic distribution of Darktrace customers.

Analysis of campaign clusters identified by the Darktrace Threat Research team during the first half of 2026 revealed distinct regional trends.

  • Europe, Middle East & Africa (EMEA) dominated with 60% of all campaign cluster cases targeting this region.
  • The Americas (AMS) was the next most affected region, with 30% of campaign cluster cases.
  • The Asia-Pacific and Japan (APJ) region was less affected by campaign clusters, potentially indicating that threat actors placed a lower priority on the region and instead focused their efforts elsewhere.

Sector targeting also varied considerably by region:

  • In EMEA, the Information and Communication was the most affected by a significant margin, representing 25% of all cases.
  • In contrast, AMS targeting was more evenly distributed, with the Education, Public administration and defence, and Financial Insurance activities sectors all forming over 20% of AMS regional cases.
  • Across APJ, campaign activity was spread more equally, with no single sector emerging as a dominant target.

Several countries also stood out within their respective regions:

  • The United States accounted for 60% of all campaign clusters within AMS.
  • Japan represented 40% of campaign customer cases across APJ.
  • In EMEA, the United Kingdom and Zimbabwe each accounted for 23% of identified cases, both being involved in a variety of campaign types.

Inside the SOC & Threat Research 2026 Monthly Progression: From Access to Impact

Month Dominant Themes
January Voice phishing, VPS infrastructure, WebSocket C2, RMM abuse, ransomware, infostealers (StealC), and trojanized installers (7-Zip).
February Voice phishing, VPN intrusion, edge infrastructure compromise (BeyondTrust), and RMM abuse.
March Sustained supply chain compromise (Hola VPN, Axios, Trivy), malicious browser extensions, phishing, and discovery tools.
April Account creation abuse, payload delivery, VPN credential abuse, Fortinet exploitation, and botnet activity.
May PowerShell, EtherHiding, data exfiltration, VPN access, business email compromise (BEC), ClickFix, and infostealers (AMOS).
June RDP abuse, device registration, RMM usage, voice phishing, cloud data theft, botnet activity, blockchain abuse, ClickFix, and infostealers (AMOS).

Appendix 3: Bibliography

External

[1] https://www.darkreading.com/cyberattacks-data-breaches/jadepuffer-first-complete-llm-driven-ransomware-attack

[2] https://www.trendmicro.com/en_us/research/26/c/pawn-storm-targets-govt-infra.html

Darktrace Reading

1.        https://www.darktrace.com/blog/ai-llm-generated-malware-used-to-exploit-react2shell

2.        https://www.darktrace.com/blog/2025-cyber-threat-landscape-darktraces-mid-year-review

3.        https://www.darktrace.com/resources/annual-threat-report-2026

4.        https://www.darktrace.com/blog/when-trust-becomes-the-attack-surface-supply-chain-attacks-in-an-era-of-automation-and-implicit-trust

5.        https://www.darktrace.com/blog/hola-vpn-abuse-from-proxy-traffic-to-malware-and-cryptomining

6.        https://www.darktrace.com/blog/security-after-signatures-operating-in-a-world-of-pre-cve-disclosure-exploitation-collapsed-trust-boundaries-and-autonomous-systems

7.        https://www.darktrace.com/blog/when-ai-infrastructure-becomes-part-of-the-attack-surface

8.        https://www.darktrace.com/blog/cve-2026-1731-how-darktrace-sees-the-beyondtrust-exploitation-wave-unfolding

9.        https://www.darktrace.com/resource/understanding-chinese-nexus-cyber-tradecraft

10.   https://www.darktrace.com/blog/chinese-apt-campaign-targets-entities-with-updated-fdmtp-backdoor

11.  https://www.darktrace.com/blog/inside-zionsiphon-darktraces-analysis-of-ot-malware-targeting-israeli-water-systems

12.  https://www.darktrace.com/resources/the-state-of-cybersecurity-in-the-finance-sector

13.  https://www.darktrace.com/blog/from-click-to-command-behavioral-detection-of-applescript-led-macos-intrusions

14.  https://www.darktrace.com/blog/the-state-of-cybersecurity-in-the-finance-sector-six-trends-to-watch

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 Jones
SVP, Global Threat Intelligence
Written by
Emma Foulger
Global Threat Research Operations Lead

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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

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Key takeaways

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

How behavioral detection helps stop prompt injection attacks

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

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

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

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

How do prompt injection attacks work?

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

Prompt injection attack example

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

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

How we tested prompt injection attacks on an enterprise agent

Summary:

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

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

Figure 1
Figure 2

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

How Darktrace detected a prompt injection attack

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

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

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

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

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

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

Why behavioral security makes a difference detecting prompt injection attacks

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

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

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

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

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

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

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

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

Why enterprise AI security requires more than guardrails

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

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

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

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

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

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

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

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

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

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

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

How to secure enterprise AI operations from prompt injection attacks

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

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

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

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

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

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

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

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