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.
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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.
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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.
No items found.
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.
From One Alert to a Wider Campaign: Uncovering Novel Threats Through Behavioral Analysis
Key Findings
Darktrace’s Threat Research team is exploring a new method to identify malicious campaigns by correlating similar anomalous activity across its customer fleet.
The method uses unsupervised clustering to identify shared behavioral patterns across multiple customer deployments without relying on prior indicators of compromise (IoCs).
The approach identified shared infrastructure across dozens of customers, with activity linked to the likely POPA botnet.
A second cluster identified anomalous activity associated with Monero cryptocurrency mining.
How does Darktrace conduct threat research?
The Darktrace Threat Research team aims to identify malicious campaign activity affecting multiple customers. By their nature, these campaigns will lead to shared behavioral patterns across multiple victims.
In this piece, we describe a method for identifying malicious campaign activity that uses this simple observation as a guiding principle. We begin by outlining a few key facts about the modern threat landscape and why behavioral detection is necessary to meet the challenges it presents. We then explore how fleet-wide behavioral detections can be leveraged using the principle above to systematically identify multi-deployment campaigns impacting the Darktrace customer fleet. Finally, we demonstrate that this research is not purely theoretical, using real examples of campaign activity detected through this novel approach.
Shifting to a behavioral-focused approach
The modern era of cyber-defense necessitates detection capabilities beyond traditional signature-based methods. Technologies such as antivirus signatures, hash-based malware identification, and IP blocklists have historically been successful in defending against known threats. However, they are easily circumvented by attackers and inherently limited in defending against the novel attack techniques that today's threat landscape is producing.
Recent breakthroughs in AI represent a transformational risk multiplier that cannot be ignored. AI systems do not merely execute existing attacks at machine speed; there are signs they can also synthesize novel tradecraft [1], increasing the likelihood that defenders will encounter attack patterns that have never previously been observed. Meanwhile vulnerability disclosures continue to accelerate. More than 48,000 CVEs were published in 2025, and published statistics to date indicate that 2026 is already on track to significantly exceed that figure [2]. While multiple factors may contribute to vulnerability discovery, AI is seen as a key factor in this rapid growth. Organizations should expect a growing proportion of malicious activity to fall outside the scope of detections that rely solely on prior knowledge of known threats.
By design, Darktrace’s behavioral and anomaly-focused detection capabilities are well-suited to this testing landscape. With a focus on detecting unknown and unexpected activity that deviates from the baseline of “normal” behavior, detection of CVE exploitation without prior knowledge of the vulnerability and before public disclosure, for example, is achievable [3][4].
Darktrace’s diverse customer base benefits from a further layer of protection: working with only deidentified alert metadata, our threat researchers hunt proactively across the fleet. Beyond the level of the individual customer, there is a second, larger vantage to be leveraged.
Darktrace data provides unique insight into the unexpected behavioral patterns that occur across its customer fleet. What can we see if we look at this fleet-wide telemetry and hunt for systematic behavioral campaigns that impact our customer base?
Correlating across the customer base
At the deployment level, Darktrace focuses on whether activity is unusual in the context of an organization's normal behavior, but as we zoom out and look at these alerts at the fleet level, the problem fundamentally changes . We are no longer seeking anomalies in largely normal data; we are seeking systematic patterns within data already known to be anomalous. An isolated behavior anomaly may be notable for a single customer; the same fingerprint across dozens is a signal of a structured campaign. Hunting for such campaigns and sharing our findings are key areas of focus for Darktrace’s Threat Research team. In this spirit, Darktrace is actively exploring a a new research approach that leverages deidentified alert metadata to increase campaign detection ability.
This approach is based on the premise that an expert human analyst presented with a set of alerts will identify likely related activity by assessing whether the metadata fields indicate a relationship. For example, two connections to a rare endpoint that exhibits naming structure that is likely from a single algorithm are a strong indicator, as is the use of an unusual port carrying a given protocol (e.g. port 6000 for SSL). Darktrace’s approach to campaign detection encodes this expert human judgement process through deterministic embedding functions that obtain reproducible vector representations of alert data. Unsupervised clustering is then applied to these vector representations to obtain groups of alerts that describe semantically similar alert data across multiple customers. These clusters therefore represent similar anomalous activity that has occurred across multiple customers. In other words, these clusters are candidates for malicious campaign activity.
Figure 1: Layers of AI-based analysis provided through Darktrace products and cross-customer correlation.
Case study 1 – unusual connections to shared underlying infrastructure
In one recent case, the clustering produced several tight groups of alerts spanning dozens of customers. Each group centered on a single domain whose subdomains were algorithmically generated (e.g. s01699, s1736, s91). Examined side by side, these clusters shared an unmistakable behavioral shape: each involved a domain with a clear naming pattern (e.g. s016841786.net-echo[.]com, s1670.pixellog[.]io, s217.pixellog[.]io) , with connections over SSL on the unusual port 6000 to servers hosted by non-mainstream providers (e.g. OVH, Hetzner, GTHost, Leaseweb), rather than generally expected content-delivery networks.
Figure 2: An example model alert triggering on unusual outbound connections and data transfer to s1670.pixellog[.]io.
Closer inspection revealed that the same subdomain label appeared under different domains (e.g. s1786.net-echo[.]com and s1786.pixellog[.]io). Following this lead, Darktrace’s threat researchers pivoted across the customer base and found numerous distinct subdomain labels reused under more than one registered domain. In several cases, the same label resolved to the same IP across different domains (e.g. s1704 under both pixellog[.]io and net-echo[.]com → 148.113.222[.]244; s01684 → 15.235.67[.]95), suggesting the use of ephemeral subdomain infrastructure in an attempt to avoid signature-based defense techniques.
This example demonstrates how multi-deployment data can uncover shared infrastructure that may be difficult to identify at the individual deployment level alone. In particular, the presented method facilitated this discovery by producing coherent, tight clusters of geometrically similar vector embeddings of malicious activity from large-scale fleet data, which could then be presented to a researcher for further investigation. This activity highlighted across the Darktrace customer base was ultimately linked to likely POPA botnet activity through use of open-source intelligence (OSINT) [5].
Case Study 2 – anomalous user agent and txt URI
A second example shows the method surfacing a single, self-contained cluster. The clustering was not given any indicators to look for; instead, it grouped devices that shared an unusual combination of features. On inspection, that shared consisted of:
- unusual user agent (tes)
- specific request path (/md5_GIP.txt)
- uncommon destination port (83)
- hostname impersonating Google (matching regular expression ^www\.google\.com\.[a-zA-Z0-9]+\.fast-dns-host\.com$)
Treating these shared features as IoCs, Darktrace’s threat researchers then pivoted to an exploration across the customer base to investigate the full breadth of the campaign. This search identified further commonalities; additional domains which shared the same IP as the domain family highlighted in the cluster, as well as evidence of cryptocurrency mining on affected devices. Additional OSINT research also aligned with these findings, linking the discovered payloads and infrastructure to Monero cryptocurrency mining [6].
Conclusion
The method outlined in this blog is under active development, with ongoing technical refinement providing opportunities to further enhance its capabilities. While the capability continues to mature, this approach to threat hunting leverages the powerful vantage point of fleetwide telemetry across a diverse customer base to help protect Darktrace customers. This method allows campaigns that at the deployment level appear as isolated alerts to be seen at their true scale and spread. It enables proactive fleet-wide analysis without prior IoCs to identify campaigns impacting Darktrace customers.
This is possible because of what the method is built on: the atomic unit is the Darktrace alert, a signal that encodes years of cyber expertise, while the multi-deployment nature of the method allows organizations to indirectly benefit from findings from other networks through shared intelligence by Darktrace’s Threat Research team.
Credit to Daniel Levy (Threat Hunting Data Scientist), Paul Jennings (Principal Cyber Analyst), Emma Foulger (Global Head, Threat Operations)
“I wonder if running that tool influenced the connectivity in some way.”
“I might need to target down or reboot, but first, I'll investigate the network using ARP. I wonder if ARP is responding properly. If I see "ip neigh stale," that could indicate a problem. I think arping might help in this situation, but I’ll need to keep an eye on how the network is behaving. It's all about figuring out where the issue lies!”
図10：エージェントの異常なLDAPアクティビティに対してトリガーされたこのLinuxサーバーに対するモデル検知は、Cyber AI Analystによって自律的に調査され、その調査結果にはエージェントの異常なSMBセッションアクティビティに関する内容が含まれ、Cyber AIAnalystインシデントに記録されました。
DarktraceのCyber AI Analystは、エージェントのアクティビティによってトリガーされたモデル検知を自律的に調査し、その調査結果を1つの重要なインシデントレポートにまとめました。インシデント報告書の内容は、エージェントによるネットワークスキャンから始まりコーディング演習内容のSMBベースの上書きで終わる、エージェントの行動の各段階を詳しくカバーしています。
図20：Cyber AI Analystは、モデル検知に対する自律的な調査を通じて得られた所見をつなぎ合わせ、エージェントの進行状況のタイムラインを作成し、アクティビティを視覚的に表したグラフとともに提供しました。
Cyber Verification Program下のAnthropic Opus 4.6モデルなど、他のフロンティアモデルを使用したエージェントも、Darktraceのシミュレートされた環境で同じ設定とタスクを使ってテストされました。反復の度に、エージェントは演習の内容または採点プログラムを変更して不正を行おうとしました。基盤となるモデルに関係なく、エージェントは自分が置かれた環境を侵害することで、100％のスコアを達成する方法を見つけることに成功していました。これらのエージェントによるハッキングは、アクティビティの内容こそ違っていましたが、すべてその環境のベースラインの振る舞いから大きく逸脱した動作を引き起こしていました。これらの逸脱はDarktraceプラットフォームに十分な検知の機会を提供し、エージェントの逃げ場はありませんでした。
