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August 26, 2020

Darktrace Detects Malicious ISO Files with AI Darktrace Email

Darktrace AI detects malicious ISO file in email attack. Learn more about how Antigena Email stopped the attack without relying on signatures or blacklists.
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
Mariana Pereira
VP, Field CISO
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26
Aug 2020

Darktrace has recently seen a string of email attacks that use some degree of social engineering to convince the recipient to open a misleading link and divulge their credentials. In this blog, we look at an email attack targeting a Spanish customer that involved hiding malicious content in an unusual file type that is not regularly checked by common email security tools.

An ISO file, often referred to as an ISO image, is an archive file that contains an identical copy of data found on an optical disc, like a CD or DVD. They are primarily used for backing up optical discs or distributing large file sets that are intended to be burned onto an optical disc. Since they are relatively unusual – and are typically extremely large files – most standard email controls don’t analyze them in any depth, if at all.

Darktrace detected one cyber-criminal using ISO files to inflict damage on a food distributor in Spain. The organization, which had adopted Antigena Email just two weeks earlier, received around 84 emails from the same sender, each containing a malicious ISO attachment. The emails were received from info@valeplaz[.]com, a clever and well-executed spoof of the email address info@valenplas[.]com, which is the contact email of a legitimate Spanish manufacturer – possibly even a supplier of the victim organization.

Figure 1: A snapshot of Antigena Email’s user interface

Darktrace noticed that the sender had never been seen in any prior correspondences across the business. Additionally, the personal field does not correspond with the header in the email itself – which is what would be visible to the recipient. In the connection IP address and checks, Darktrace’s AI revealed that the true sender does not correspond with the domain valeplaz[.]com.

The subject line suggests that the email is about an order the client made. Analyzing the attachments, Darktrace surfaced a file titled URGENTE_PO_120620.iso. The name of the file suggests the sender is attempting to use the social engineering tactic of urgency in order to alarm the recipients, leading them to jump into action and click a link or open attachments without carefully considering the details of the email.

Darktrace’s AI also recognized that the file extension .iso is highly anomalous for the group, user, and the organization as a whole. Even more suspiciously, the size of the attachment is incredibly small (just 485.4 kB), which makes it highly unlikely that it was, in fact, a genuine invoice in the form of a PDF or Word attachment. These findings, in conjunction with the New Contact and Wide Distribution tags of the email, caused Antigena Email to strip the email of the attachment and hold it back from each recipient’s inbox. In addition, Darktrace’s AI revealed that the email contained an anomalous link which it deemed highly suspicious, and locked the link in all emails while the security team investigated the incident.

Figure 2: The suspicious link in question

Stopping the attack without a Patient Zero

When the security team later checked the file hash on the attachment, they discovered that some anti-virus vendors, including Microsoft, had already labelled it as malware. The crucial challenge is to stop the malicious email in the first instance – before it lands in the first inbox. With a continuously updated understanding of ‘self’, Darktrace’s AI is able to do just that – stopping attacks without requiring a ‘Patient Zero’ be infected.

Moreover, many legacy solutions hadn’t yet recognized this file hash as malicious, suggesting that this was a relatively new attack. This exposes an increasingly obvious limitation of such tools – attackers are refreshing their attack infrastructure so often that no matter how frequently legacy tools or blacklists are updated, they are outdated almost immediately.

Antigena Email caught this attack without relying on any signatures and blacklists, but instead by learning whether or not the email, file, and behavior was normal for the unique business. With Cyber AI protecting their inbox, this organization was able to thwart this attack in the first instance – before any emails landed in an inbox or any employees clicked on the link.

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
Mariana Pereira
VP, Field CISO

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April 28, 2026

State of AI Cybersecurity 2026: 87% of security professionals are seeing more AI-driven threats, but few feel ready to stop them

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The findings in this blog are taken from Darktrace’s annual State of AI Cybersecurity Report 2026.

In part 1 of this blog series, we explored how AI is remaking the attack surface, with new tools, models, agents — and vulnerabilities — popping up just about everywhere. Now embedded in workflows across the enterprise, and often with far-reaching access to sensitive data, AI systems are quickly becoming a favorite target of cyber threat actors.

Among bad actors, though, AI is more often used as a tool than a target. Nearly 62% of organizations  experienced a social engineering attack involving a deepfake, or an incident in which bad actors used AI-generated video or audio to try to trick a biometric authentication system, compared to 32% that reported an AI prompt injection attack.

In the hands of attackers, AI can do many things. It’s being used across the entire kill chain: to supercharge reconnaissance, personalize phishing, accelerate lateral movement, and automate data exfiltration. Evidence from Anthropic demonstrates that threat actors have harnessed AI to orchestrate an entire cyber espionage campaign from end to end, allegedly running it with minimal human involvement.

CISOs inhabit a world where these increasingly sophisticated attacks are ubiquitous. Naturally, combatting AI-powered threats is top of mind among security professionals, but many worry about whether their capabilities are up to the challenge.

AI-powered threats at scale: no longer hypothetical

AI-driven threats share signature characteristics. They operate at speed and scale. Automated tools can probe multiple attack paths, search for multiple vulnerabilities and send out a barrage of phishing emails, all within seconds. The ability to attack everywhere at once, at a pace that no human operator could sustain, is the hallmark of an AI-powered threat. AI-powered threats are also dynamic. They can adapt their behavior to spread across a network more efficiently or rewrite their own code to evade detection.

Security teams are seeing the signs that they’re fighting AI-powered threats at every stage of the kill chain, and the sophistication of these threats is testing their resolve and their resources.

  • 73% say that AI-powered cyber threats are having a significant impact on their organization
  • 92% agree that these threats are forcing them to upgrade their defenses
  • 87% agree that AI is significantly increasing the sophistication and success rate of malware
  • 87% say AI is significantly increasing the workload of their security operations team

These teams now confront a challenge unlike anything they’ve seen before in their careers, and the risks are compounding across workflows, tools, data, and identities. It’s no surprise that 66% of security professionals say their role is more stressful today than it was five years ago, or that 47% report feeling overwhelmed at work.

Up all night: Security professionals’ worry list is long

Traditional security methods were never built to handle the complexity and subtlety of AI-driven behavior. Working in the trenches, defenders have deep firsthand experience of how difficult it can be to detect and stop AI-assisted threats.

Increasingly effective social engineering attacks are among their top concerns. 50% of security leaders mentioned hyper-personalized phishing campaigns as one of their biggest worries, while 40% voiced apprehension about deepfake voice fraud. These concerns are legitimate: AI-generated phishing emails are increasingly tailored to individual organizations, business activities, or individuals. Gone are the telltale signs – like grammar or spelling mistakes – that once distinguished malicious communications. Notably, 33% of the malicious emails Darktrace observed in 2025 contained over 1,000 characters, indicating probable LLM usage.

Security leaders also worry about how bad actors can leverage AI to make attacks even faster and more dynamic. 45% listed automated vulnerability scanning and exploit chaining among their biggest concerns, while 40% mentioned adaptive malware.

Confidence is lacking

Protecting against AI demands capabilities that many organizations have not yet built. It requires interpreting new indicators, uncovering the subtle intent within interactions, and recognizing when AI behavior – human or machine – could be suspicious. Leaders know that their current tools aren’t prepared for this. Nearly half don’t feel confident in their ability to defend against AI-powered attacks.

We’ve asked participants in our survey about their confidence for the last three years now. In 2024, 60% said their organizations were not adequately prepared to defend against AI-driven threats. Last year, that percentage shrunk to 45%, a possible indicator that security programs were making progress. Since then, however, the progress has apparently stalled. 46% of security leaders now feel inadequately prepared to protect their organizations amidst the current threat landscape.

Some of these differences are accentuated across different cultures. Respondents in Japan are far less confident (77% say they are not adequately prepared) than respondents in Brazil (where only 21% don’t feel prepared).

Where security programs are falling short

It’s no longer the case that cybersecurity is overlooked or underfunded by executive leadership. Across industries, management recognizes that AI-powered threats are a growing problem, and insufficient budget is near the bottom of most CISO’s list of reasons that they struggle to defend against AI-powered threats.  

It’s the things that money can’t buy – experience, knowledge, and confidence – that are holding programs back. Near the top of the list of inhibitors that survey participants mention is “insufficient knowledge or use of AI-driven countermeasures.” As bad actors embrace AI technologies en masse, this challenge is coming into clearer focus: attack-centric security tools, which rely on static rules, signatures, and historical attack patterns, were never designed to handle the complexity and subtlety of AI-driven attacks. These challenges feel new to security teams, but they are the core problems Darktrace was built to solve.  

Our Self-Learning AI develops a deep understanding of what “normal” looks like for your organization –including unique traffic patterns, end user habits, application and device profiles – so that it can detect and stop novel, dynamic threats at the first encounter. By focusing on learning the business, rather than the attack, our AI can keep pace with AI-powered threats as they evolve.

Explore the full State of AI Cybersecurity 2026 report for deeper insights into how security leaders are responding to AI-driven risks.

Learn more about securing AI in your enterprise.

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April 24, 2026

Email-Borne Cyber Risk: A Core Challenge for the CISO in the Age of Volume and Sophistication

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The challenge for CISOs

Despite continuous advances in security technologies, humans continue to be exploited by attackers. Credential abuse and social actions like phishing are major factors, accounting for around 60% of all breaches. These attacks rely less on technical vulnerabilities and more on exploiting human behavior and organizational processes. 

From my perspective as a former CISO, protecting humans concentrates three of today’s most pressing challenges: the sheer volume of email-based threats, their increasing sophistication, and the limitations of traditional employee awareness programs in moving the needle on risk. 

My personal experience of security awareness training as a CISO

With over 20 years’ experience as an ICT and Cybersecurity leader across various international organizations, I’ve seen security awareness training (SAT) in many guises. And while the cyber landscape is evolving in every direction, the effectiveness of SAT is reaching a plateau.  

Most programs I’ve seen follow a familiar pattern. Training is delivered through a combination of eLearning modules and internal sessions designed to reinforce IT policies. Employees are typically required to complete a slide deck or video, followed by a multiple-choice quiz. Occasional phishing simulations are distributed throughout the year.

The content is often static and unpersonalized, based on known threats that may already be outdated. Every employee regardless of role or risk exposure receives the same training and the same simulated phishing templates, from front-desk staff to the CEO.

The problem with traditional SAT programs

The issue with the approach to SAT outlined above is that the distribution of power is imbalanced. Humans will always be fallible, particularly when faced with increasingly sophisticated attacks. Providing generic, low-context training risks creating false confidence rather than genuine resilience. Let’s look at some of the problems in detail.

Timing and delivery

Employees today operate under constant cognitive load, making lots of rapid decisions every day to reduce their email volumes. Yet if employees are completing training annually, or on an ad hoc basis, it becomes a standalone occurrence rather than a continuous habit.  

As a result, retention is low. Employees often forget the lessons within weeks, a phenomenon known as the ‘Ebbinghaus Forgetting Curve.’

The graph illustrates that when you first learn something, the information disappears at an exponential rate without retention. In fact, according to the curve, you forget 50% of all new information within a day, and 90% of all new information within a week.  

Simultaneously, most training is conducted within a separate interface. Because it takes place away from the actual moment of decision-making, the "teachable moment" is lost. There is a cognitive disconnect between the action (clicking a link in Outlook) and the education (watching a video in a browser). 

People

In the context of professional risk management, the risks faced by different users are different. Static learning such as everyone receiving the same ‘Password Reset’ email doesn’t help users prepare for the specific threats they are likely to face. It also contributes to user fatigue, driven by repetitive training. And if users receive tests at the same time, news spreads among colleagues, hurting the efficacy of the test.  

Staff turnover introduces further risk. In many organizations, new employees gain access to systems before receiving meaningful training, reducing onboarding to little more than policy acknowledgment.

Measuring success

In my experience, solutions are standalone, without any correlation to other tools in the security stack. In some cases, the programs are delivered by HR rather than the security team, creating a complete silo.  

As a result, SAT is often perceived as a compliance exercise rather than a capability building function. The result is that poor-quality training does little to reduce the likelihood of compromise, regardless of completion rates or quiz performance.

What a modern SAT solution should look like

For today’s CISO, email represents the convergence point of high-volume, high-impact, and human-centric threats. Despite significant security investments, it remains one of the most difficult channels to secure effectively. Given these constraints, CISOs must evolve their approach to SAT.

Success lies in a balanced strategy one that combines advanced technology, attack surface reduction, and pragmatic user enablement, without over-relying on human vigilance as the final line of defense.

This means moving beyond traditional SAT toward continuous, contextual awareness, realistic simulations, and tight integration with security outcomes.

Three requirements for a modern SAT solution

  • Invisible protection: The optimum security solution is one that assists users without impeding their experience. The objective is to enhance human capabilities, rather than simply delivering a lecture. 
  • Real-time feedback: Rather than a monthly quiz, the ideal system would provide a prompt or warning when a user is about to engage with something suspicious. 
  • Positive culture: Shifting the focus away from a "gotcha" culture, which is a contributing factor to a resentment, and instead empowers employees to serve as "sensors" for the company. 

Discover how personalized security coaching can strengthen your human layer and make your email defenses more resilient. Explore Darktrace / Adaptive Human Defense.

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About the author
Karim Benslimane
VP, Field CISO
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