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October 20, 2021

Analyzing the Resurgence of Ryuk Ransomware

Understand the latest developments in Ryuk ransomware and how its return affects organizations facing increased cyber threats.
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
Brianna Luong (Leddy)
Sr. Technical Alliances Manager
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20
Oct 2021

In the era of international-scale cyber-warfare, focus has started to move away from small-time cyber thieves toward well-known, well-funded and sometimes government-backed cyber-crime organizations. Cyber-attacks sometimes work on discordant scales, however, and it doesn’t always take big budgets or key players for considerable damage to be dealt.

Numerous stories detail how the criminal and the curious alike have single-handedly breached some of the most secure systems in the world. At the more amusing end, there’s the story of Kristoffer von Hassel who discovered a novel exploit in Microsoft’s Xbox Live system at just five years old. And then of course there are those who hack their way right into promising security careers by breaching systems at major organizations. However, genuine damage has been done by individual threat actors as well.

These might be criminals using second-hand offensive tools, buying botnet armies for as little as $10 on the Dark Web, or using ransomware files downloaded for free. But ultimately, even a single cyber-criminal can inflict crippling damage upon large organizations if they are given the opportunity.

This is especially the case when the tools in their possession have been developed by some of the most notorious names in cyber-crime.

Copycat criminals

In early 2021, Darktrace detected a new instance of the once notorious Ryuk ransomware being launched against a business in the APAC region. The detection was intriguing.

The developers of Ryuk, a prolific cyber-criminal organization given the name ‘Wizard Spider’, had long since abandoned it in favor of a successor called ‘Conti’. Wizard Spider have launched some of the largest cyber-attacks in recent history, allegedly with the support of the Russian government, and are under investigation by Interpol and the FBI. They are not known for using outdated tools.

It soon became clear that this attack was not being launched by Wizard Spider at all, but by small-scale threat actors picking up the tools Wizard Spider left behind. And as the new attackers proved, these tools are still far from defunct.

Ryuk ransomware: A city-stopper for sale

Ryuk ransomware is commonly used to target large enterprise environments, even taking down entire city councils in some instances. Lake City, Florida and the City of Onkaparinga in South Australia are two of its known victims, along with numerous schools and hospitals across the US.

Once active in a system, Ryuk uses a combination of symmetric (AES) and asymmetric (RSA) encryption to encrypt files, disabling Windows’ system restore feature as it does so, and generally demands payment via Bitcoin in return for a private decryption key.

Though Ryuk was not initially sold in the same manner as its predecessor, Hermes, on the Dark Web site ‘exploit[.]in’, it is now believed by some publications that the toolkit must be available somewhere for various threat actors to buy and tailor to their requirements. This explains its recurrence beyond Wizard Spider activities.

New dog, old tricks

Darktrace spotted the new instance of Ryuk during a trial with a real estate business in the APAC region. The first warning sign came when some basic .dat files were downloaded onto one of the business’ devices from an unknown Russian IP address. Darktrace immediately detected that this download was a likely breach and, had Antigena been set up in active mode, would have initiated a targeted response at this early stage.

The .dat files on the infected device allowed the attackers to use RDP (Remote Desktop Protocol) to spread further into the business’ network. Two days after the initial compromise, the threat actor had gained administrative credentials through a bruteforce attack and could begin scanning the network further.

Figure 1: Timeline of the attack

The witching hour

Just an hour after the attacker gained administrative credentials, at approximately 3:30am local time, ransomware files appeared in the business’ network. This timing was not accidental. The attackers knew that the security teams at the target business were home and asleep when the ransomware landed in the small hours of the morning, giving them plenty of time to conduct their attack.

This is precisely the kind of simple tactic which can multiply the scale of an attack without using large budgets or complex toolsets. The Ryuk ransomware rapidly began encrypting corporate files during the night, and by the time the security team returned in the morning, all they could do was shut down the entire network and hope to limit the spread of Ryuk, if only to save a few final devices.

The total attack time, from initial compromise to widespread data encryption, was just two and a half days. Whether due to understaffing or preoccupation, the security team did not find the time in that small window to respond to alerts, and, with Darktrace Antigena in passive mode, the attack was able to go ahead. This business’ need for Autonomous Response, which can protect against old and new attacks around the clock without the need for manual intervention, was painfully apparent.

Autonomous Response: Stop Ryuk before Ryuk stops you

Understanding Ryuk’s history and functionality does little good for organizations when it is still capable of eluding their defenses and catching security teams unawares. Darktrace’s Self-Learning AI is uniquely positioned to address these sophisticated threats, even as they evolve in the hands of different attackers and become unrecognizable to traditional rule-based security approaches.

Utilizing 24/7 Autonomous Response to stop both new and old threats at machine speed gives security teams the best chance of leveling the playing field against attackers. With Darktrace Antigena, the size or status of the attacking organization and their toolset is irrelevant – any anomalous and threatening behavior will be neutralized quickly and accurately, before damage can be done.

Thanks to Darktrace analyst Thomas Nommensen for his insights on the above threat find.

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
Brianna Luong (Leddy)
Sr. Technical Alliances Manager

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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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