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March 29, 2023

Email Security & Future Innovations: Educating Employees

As online attackers change to targeted and sophisticated attacks, Darktrace stresses the importance of protection and utilizing steady verification codes.
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
Dan Fein
VP, Product
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29
Mar 2023

In an escalating threat landscape with email as the primary target, IT teams need to move far beyond traditional methods of email security that haven’t evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. By design, they are permanently playing catch up to continually innovating attackers, taking an average of 13 days to recognize new attacks[1]

Phishing attacks are getting more targeted and sophisticated as attackers innovate in two key areas: delivery tactics, and social engineering. On the malware delivery side, attackers are increasingly ‘piggybacking’ off the legitimate infrastructure and reputations of services like SharePoint and OneDrive, as well as legitimate email accounts, to evade security tools. 

To evade the human on the other end of the email, attackers are tapping into new social engineering tactics, exploiting fear, uncertainty, and doubt (FUD) and evoking a sense of urgency as ever, but now have tools at their disposal to enable tailored and personalized social engineering at scale. 

With the help of tools such as ChatGPT, threat actors can leverage AI technologies to impersonate trusted organizations and contacts – including damaging business email compromises, realistic spear phishing, spoofing, and social engineering. In fact, Darktrace found that the average linguistic complexity of phishing emails has jumped by 17% since the release of ChatGPT.  

This is just one example of accelerating attack sophistication – lowering the barrier to entry and improving outcomes for attackers. It forms part of a wider trend of the attack landscape moving from low-sophistication, low-impact, and generic phishing tactics - a 'spray and pray' approach - to more targeted, sophisticated, and higher impact attacks that fall outside of the typical detection remit for any tool relying on rules and signatures. Generative AI and other technologies in the attackers' toolkit will soon enable the launch of these attacks at scale, and only being able to catch known threats that have been seen before will no longer be enough.

Figure 1: The progression of attacks and relative coverage of email security tools

In an escalating threat landscape with email as the primary target, the vast majority of email security tools haven't evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. They look to the past to try and predict the next attack, and are designed to catch today’s attacks tomorrow.

Organizations are increasingly moving towards AI systems, but not all AI is the same, and the application of that AI is crucial. IT and security teams need to move towards email security that is context-aware and leverages AI for deep behavioral analysis. And it’s a proven approach, successfully catching attacks that slip by other tools across thousands of organizations. And email security today needs to be more about just protecting the inbox. It needs to address not just malicious emails, but the full 360-degree view of a user across their email messages and accounts, as well as extended coverage where email bleeds into collaboration tools/SaaS. For many organizations, the question is not if they should upgrade their email security, but when – how much longer can they risk relying on email security that’s stuck looking to the past?  

The Email Security Industry: Playing Catch-Up

Gateways and ICES (Integrated Cloud Email Security) providers have something in common: they look to past attacks in order to try to predict the future. They often rely on previous threat intelligence and on assembling ‘deny-lists’ of known bad elements of emails already identified as malicious – these tools fail to meet the reality of the contemporary threat landscape. Some of these tools attempt to use AI to improve this flawed approach, looking not only for direct matches, but using "data augmentation" to try and find similar-looking emails. But this approach is still inherently blind to novel threats. 

These tools tend to be resource-intensive, requiring constant policy maintenance combined with the hand-to-hand combat of releasing held-but-legitimate emails and holding back malicious phishing emails. This burden of manually releasing individual emails typically falls on security teams, teams that are frequently small with multiple areas of responsibility. The solution is to deploy technology that autonomously stops the bad while allowing the good through, and adapts to changes in the organization – technology that actually fits the definition of ‘set and forget’.  

Becoming behavioral and context-aware  

There is a seismic shift underway in the industry, from “secure” email gateways to intelligent AI-driven thinking. The right approach is to understand the behaviors of end users – how each person uses their inbox and what constitutes ‘normal’ for each user – in order to detect what’s not normal. It makes use of context – how and when people communicate, and with who – to spot the unusual and to flag to the user when something doesn’t look quite right – and why. Basically, a system that understands you. Not past attacks.  

Darktrace has developed a fundamentally different approach to AI, one that doesn’t learn what’s dangerous from historical data but from a deep continuous understanding of each organization and their users. Only a complex understanding of the normal day-to-day behavior of each employee can accurately determine whether or not an email actually belongs in that recipient’s inbox. 

Whether it’s phishing, ransomware, invoice fraud, executive impersonation, or a novel technique, leveraging AI for behavioral analysis allows for faster decision-making – it doesn’t need to wait for a Patient Zero to contain a new attack because it can stop malicious threats on first encounter. This increased confidence in detection allows for more a precise response – targeted action to remove only the riskiest parts of an email, rather than taking a broad blanket response out of caution – in order to reduce risk with minimal disruption to the business. 

Returning to our attack spectrum, as the attack landscape moves increasingly towards highly sophisticated attacks that use novel or seemingly legitimate infrastructure to deliver malware and induce victims, it has never been more important to detect and issue an appropriate response to these high-impact and targeted attacks. 

Fig 2: How Darktrace combined with native email security to cover the full spectrum of attacks

Understanding you and a 360° view of the end user  

We know that modern email security isn’t limited to the inbox alone – it has to encompass a full understanding of a user’s normal behavior across email and beyond. Traditional email tools are focused solely on inbound email as the point of breach, which fails to protect against the potentially catastrophic damage caused by a successful email attack once an account has been compromised.    

Fig 3: A 360° understanding of a user reveals their digital touchpoints beyond Microsoft

In order to have complete context around what is normal for a user, it’s crucial to understand their activity within Microsoft 365, Google Workspace, Salesforce, Dropbox, and even their device on the network. Monitoring devices (as well as inboxes) for symptoms of infection is crucial to determining whether or not an email has been malicious, and if similar emails need to be withheld in the future. Combining with data from cloud apps enables a more holistic view of identity-based attacks. 

Understanding a user in the context of the whole organization – which also means network, cloud, and endpoint data – brings additional context to light to improve decision making, and connecting email security with external data on the attack surface can help proactively find malicious domains, so that defenses can be hardened before an attack is even launched.

Educating and Engaging Your Employees

Ultimately, it’s employees who interact with any given email. If organizations can successfully empower this user base, they will end up with a smarter workforce, fewer successful attacks, and a security team with more time on their hands for better, strategic work. 

The tools that succeed best will be those that can leverage AI to help employees become more security-conscious. While some emails are evidently malicious and should never enter an employee’s inbox, there is a significant grey area of emails that have potentially risky elements. The majority of security tools will either withhold these emails completely – even though they might be business critical – or let them through scot-free. But what if these grey-area emails could in fact be used as training opportunities?    

As opposed to phishing simulation vendors, behavioral AI can improve security awareness holistically throughout organizations by training users with a light touch via their own inboxes – bringing the end user into the loop to harden defenses.  

The new frontier of email security fights AI with AI, and organizations who lag behind might end up learning the hard way. Read on for our blog series about how these technologies can transform the employee experience, dynamize deployment, augment security teams and form part of an integrated defensive loop.    

[1] 13 days is the mean average of phishing payloads active in the wild between the response of Darktrace/Email compared to the earliest of 16 independent feeds submitted by other email security technologies.

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
Dan Fein
VP, Product

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May 1, 2026

How email-delivered prompt injection attacks can target enterprise AI – and why it matters

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What are email-delivered prompt injection attacks?

As organizations rapidly adopt AI assistants to improve productivity, a new class of cyber risk is emerging alongside them: email-delivered AI prompt injection. Unlike traditional attacks that target software vulnerabilities or rely on social engineering, this is the act of embedding malicious or manipulative instructions into content that an AI system will process as part of its normal workflow. Because modern AI tools are designed to ingest and reason over large volumes of data, including emails, documents, and chat histories, they can unintentionally treat hidden attacker-controlled text as legitimate input.  

At Darktrace, our analysis has shown an increase of 90% in the number of customer deployments showing signals associated with potential prompt injection attempts since we began monitoring for this type of activity in late 2025. While it is not always possible to definitively attribute each instance, internal scoring systems designed to identify characteristics consistent with prompt injection have recorded a growing number of high-confidence matches. The upward trend suggests that attackers are actively experimenting with these techniques.

Recent examples of prompt injection attacks

Two early examples of this evolving threat are HashJack and ShadowLeak, which illustrate prompt injection in practice.

HashJack is a novel prompt injection technique discovered in November 2025 that exploits AI-powered web browsers and agentic AI browser assistants. By hiding malicious instructions within the URL fragment (after the # symbol) of a legitimate, trusted website, attackers can trick AI web assistants into performing malicious actions – potentially inserting phishing links, fake contact details, or misleading guidance directly into what appears to be a trusted AI-generated output.

ShadowLeak is a prompt injection method to exfiltrate PII identified in September 2025. This was a flaw in ChatGPT (now patched by OpenAI) which worked via an agent connected to email. If attackers sent the target an email containing a hidden prompt, the agent was tricked into leaking sensitive information to the attacker with no user action or visible UI.

What’s the risk of email-delivered prompt injection attacks?

Enterprise AI assistants often have complete visibility across emails, documents, and internal platforms. This means an attacker does not need to compromise credentials or move laterally through an environment. If successful, they can influence the AI to retrieve relevant information seamlessly, without the labor of compromise and privilege escalation.

The first risk is data exfiltration. In a prompt injection scenario, malicious instructions may be embedded within an ordinary email. As in the ShadowLeak attack, when AI processes that content as part of a legitimate task, it may interpret the hidden text as an instruction. This could result in the AI disclosing sensitive data, summarizing confidential communications, or exposing internal context that would otherwise require significant effort to obtain.

The second risk is agentic workflow poisoning. As AI systems take on more active roles, prompt injection can influence how they behave over time. An attacker could embed instructions that persist across interactions, such as causing the AI to include malicious links in responses or redirect users to untrusted resources. In this way, the attacker inserts themselves into the workflow, effectively acting as a man-in-the-middle within the AI system.

Why can’t other solutions catch email-delivered prompt injection attacks?

AI prompt injection challenges many of the assumptions that traditional email security is built on. It does not fit the usual patterns of phishing, where the goal is to trick a user into clicking a link or opening an attachment.  

Most security solutions are designed to detect signals associated with user engagement: suspicious links, unusual attachments, or social engineering cues. Prompt injection avoids these indicators entirely, meaning there are fewer obvious red flags.

In this case, the intention is actually the opposite of user solicitation. The objective is simply for the email to be delivered and remain in the inbox, appearing benign and unremarkable. The malicious element is not something the recipient is expected to engage with, or even notice.

Detection is further complicated by the nature of the prompts themselves. Unlike known malware signatures or consistent phishing patterns, injected prompts can vary widely in structure and wording. This makes simple pattern-matching approaches, such as regex, unreliable. A broad rule set risks generating large numbers of false positives, while a narrow one is unlikely to capture the diversity of possible injections.

How does Darktrace catch these types of attacks?

The Darktrace approach to email security more generally is to look beyond individual indicators and assess context, which also applies here.  

For example, our prompt density score identifies clusters of prompt-like language within an email rather than just single occurrences. Instead of treating the presence of a phrase as a blocking signal, the focus is on whether there is an unusual concentration of these patterns in a way that suggests injection. Additional weighting can be applied where there are signs of obfuscation. For example, text that is hidden from the user – such as white font or font size zero – but still readable by AI systems can indicate an attempt to conceal malicious prompts.

This is combined with broader behavioral signals. The same communication context used to detect other threats remains relevant, such as whether the content is unusual for the recipient or deviates from normal patterns.

Ask your email provider about email-delivered AI prompt injection

Prompt injection targets not just employees, but the AI systems they rely on, so security approaches need to account for both.

Though there are clear indications of emerging activity, it remains to be seen how popular prompt injection will be with attackers going forward. Still, considering the potential impact of this attack type, it’s worth checking if this risk has been considered by your email security provider.

Questions to ask your email security provider

  • What safeguards are in place to prevent emails from influencing AI‑driven workflows over time?
  • How do you assess email content that’s benign for a human reader, but may carry hidden instructions intended for AI systems?
  • If an email contains no links, no attachments, and no social engineering cues, what signals would your platform use to identify malicious intent?

Visit the Darktrace / EMAIL product hub to discover how we detect and respond to advanced communication threats.  

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product

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April 30, 2026

Mythos vs Ethos: Defending in an Era of AI‑Accelerated Vulnerability Discovery

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Anthropic’s Mythos and what it means for security teams

Recent attention on systems such as Anthropic Mythos highlights a notable problem for defenders. Namely that disclosure’s role in coordinating defensive action is eroding.

As AI systems gain stronger reasoning and coding capability, their usefulness in analyzing complex software environments and identifying weaknesses naturally increases. What has changed is not attacker motivation, but the conditions under which defenders learn about and organize around risk. Vulnerability discovery and exploitation increasingly unfold in ways that turn disclosure into a retrospective signal rather than a reliable starting point for defense.

Faster discovery was inevitable and is already visible

The acceleration of vulnerability discovery was already observable across the ecosystem. Publicly disclosed vulnerabilities (CVEs) have grown at double-digit rates for the past two years, including a 32% increase in 2024 according to NIST, driven in part by AI even prior to Anthropic’s Mythos model. Most notably XBOW topped the HackerOne US bug bounty leaderboard, marking the first time an autonomous penetration tester had done so.  

The technical frontier for AI capabilities has been described elsewhere as jagged, and the implication is that Mythos is exceptional but not unique in this capability. While Mythos appears to make significant progress in complex vulnerability analysis, many other models are already able to find and exploit weaknesses to varying degrees.  

What matters here is not which model performs best, but the fact that vulnerability discovery is no longer a scarce or tightly bounded capability.

The consequence of this shift is not simply earlier discovery. It is a change in the defender-attacker race condition. Disclosure once acted as a rough synchronization point. While attackers sometimes had earlier knowledge, disclosure generally marked the moment when risk became visible and defensive action could be broadly coordinated. Increasingly, that coordination will no longer exist. Exploitation may be underway well before a CVE is published, if it is published at all.

Why patch velocity alone is not the answer

The instinctive response to this shift is to focus on patching faster, but treating patch velocity as the primary solution misunderstands the problem. Most organizations are already constrained in how quickly they can remediate vulnerabilities. Asset sprawl, operational risk, testing requirements, uptime commitments, and unclear ownership all limit response speed, even when vulnerabilities are well understood.

If discovery and exploitation now routinely precede disclosure, then patching cannot be the first line of defense. It becomes one necessary control applied within a timeline that has already shifted. This does not imply that organizations should patch less. It means that patching cannot serve as the organizing principle for defense.

Defense needs a more stable anchor

If disclosure no longer defines when defense begins, then defense needs a reference point that does not depend on knowing the vulnerability in advance.  

Every digital environment has a behavioral character. Systems authenticate, communicate, execute processes, and access resources in relatively consistent ways over time. These patterns are not static rules or signatures. They are learned behaviors that reflect how an organization operates.

When exploitation occurs, even via previously unknown vulnerabilities, those behavioral patterns change.

Attackers may use novel techniques, but they still need to gain access, create processes, move laterally, and will ultimately interact with systems in ways that diverge from what is expected. That deviation is observable regardless of whether the underlying weakness has been formally named.

In an environment where disclosure can no longer be relied on for timing or coordination, behavioral understanding is no longer an optional enhancement; it becomes the only consistently available defensive signal.

Detecting risk before disclosure

Darktrace’s threat research has consistently shown that malicious activity often becomes visible before public disclosure.

In multiple cases, including exploitation of Ivanti, SAP NetWeaver, and Trimble Cityworks, Darktrace detected anomalous behavior days or weeks ahead of CVE publication. These detections did not rely on signatures, threat intelligence feeds, or awareness of the vulnerability itself. They emerged because systems began behaving in ways that did not align with their established patterns.

This reflects a defensive approach grounded in ‘Ethos’, in contrast to the unbounded exploration represented by ‘Mythos’. Here, Mythos describes continuous vulnerability discovery at speed and scale. Ethos reflects an understanding of what is normal and expected within a specific environment, grounded in observed behavior.

Revisiting assume breach

These conditions reinforce a principle long embedded in Zero Trust thinking: assume breach.

If exploitation can occur before disclosure, patching vulnerabilities can no longer act as the organizing principle for defense. Instead, effective defense must focus on monitoring for misuse and constraining attacker activity once access is achieved. Behavioral monitoring allows organizations to identify early‑stage compromise and respond while uncertainty remains, rather than waiting for formal verification.

AI plays a critical role here, not by predicting every exploit, but by continuously learning what normal looks like within a specific environment and identifying meaningful deviation at machine speed. Identifying that deviation enables defenders to respond by constraining activity back towards normal patterns of behavior.

Not an arms race, but an asymmetry

AI is often framed as fueling an arms race between attackers and defenders. In practice, the more important dynamic is asymmetry.

Attackers operate broadly, scanning many environments for opportunities. Defenders operate deeply within their own systems, and it’s this business context which is so significant. Behavioral understanding gives defenders a durable advantage. Attackers may automate discovery, but they cannot easily reproduce what belonging looks like inside a particular organization.

A changed defensive model

AI‑accelerated vulnerability discovery does not mean defenders have lost. It does mean that disclosure‑driven, patch‑centric models no longer provide a sufficient foundation for resilience.

As vulnerability volumes grow and exploitation timelines compress, effective defense increasingly depends on continuous behavioral understanding, detection that does not rely on prior disclosure, and rapid containment to limit impact. In this model, CVEs confirm risk rather than define when defense begins.

The industry has already seen this approach work in practice. As AI continues to reshape both offense and defense, behavioral detection will move from being complementary to being essential.

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About the author
Andrew Hollister
Principal Solutions Engineer, Cyber Technician
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