Blog
/
/
May 18, 2021

The Dangers of Double Extortion Ransomware Attacks

Learn about the latest trend in ransomware attacks known as double extortion. Discover how Darktrace can help protect your organization from this threat.
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
Default blog image
18
May 2021

A year and a half ago, ‘double extortion’ ransomware was being used by only one known threat actor. Now, over 16 ransomware groups actively utilize this tactic. So, what is it, and why has it become so popular?

What is double extortion ransomware?

The traditional story of ransomware was one of malicious code rapidly encrypting files with public-key RSA encryption, and then deleting those files if the victim did not pay the ransom.

However, after the infamous WannaCry and NotPetya ransomware campaigns over 2017, companies ramped up their cyber defense. More emphasis was placed on backups and restoration processes, so that even if files were destroyed, organizations had copies in place and could easily restore their data.

Yet in turn, cyber-criminals have also adapted their techniques. Now, rather than just encrypting files, double extortion ransomware exfiltrates the data first. This means that if the company refuses to pay up, information can be leaked online or sold to the highest bidder. Suddenly, all those backups and data recovery plans became worthless.

Maze ransomware and friends

In late 2019, Maze ransomware emerged as the first high-profile case of double extortion. Other strains soon followed, with the Sodinokibi attack — which crippled foreign exchange company Travelex — occurring on the final day of that year.

By mid-2020, hundreds of organizations were falling victim to double extortion attacks, various websites on the dark net were leaking company data, and the Ransomware-as-a-Service business was booming as developers sold and rented new types of malware.

Furthermore, cyber security regulations started being weaponized by cyber-criminals who could leverage the threat of having to pay a hefty compliance fine (CCPA, GDPR, NYSDFS regulations) to encourage their victims to keep quiet by offering them a ransom smaller than the penalty fee.

There were 1,200 double extortion ransomware incidents in 2020, across 63 countries, with over 60% of these aimed at the US and the UK.

Despite new legislation being written regularly to try and mitigate these attacks, they aren’t slowing down. According to a recent study by RUSI, there were 1,200 double extortion ransomware incidents in 2020 alone, across 63 different countries. 60% of these were aimed at organizations headquartered in the US, and the UK suffered the second highest number of breaches.

Last month, the cyber-criminal gang known as REvil released details about Apple’s new Macbook Pro on their site ‘Happy Blog’, threatening to release more blueprints and demanding a ransom of $50 million. And last week, Colonial Pipeline purportedly paid $5 million in bitcoin to recover from a devastating OT ransomware attack.

Anatomy of a double extortion ransomware attack

Darktrace has detected a huge upsurge in double extortion ransomware threats in the last year, most recently at an energy company based in Canada. The hackers had clearly done their homework, tailoring the attack to the company and moving quickly and stealthily once inside. Below is a timeline of this real-world incident, which was mostly carried out in the space of 24 hours.

Figure 1: A timeline of the attack

Darktrace detected every stage of the intrusion and notified the security team with high-priority alerts. If Darktrace Antigena had been active in the environment, the compromised server would have been isolated as soon as it began to behave anomalously, preventing the infection from spreading.

Encryption and exfiltration

The initial infection vector is not known, but the admin account was compromised most likely from a phishing link or a vulnerability exploit. This is indicative of a trend away from the widespread ‘spray and pray’ ransomware campaigns of the last decade, towards a more targeted approach.

Cyber AI identified an internal server engaging in unusual network scanning and attempted lateral movement using the Remote Desktop Protocol (RDP). Compromised admin credentials were used to spread rapidly from the server to another internal device, ‘serverps’.

The device ‘serverps’ initiated an outbound connection to TeamViewer, a legitimate file storage service, which was active for nearly 21 hours. This connection was used for remote control of the device and to facilitate the further stages of attack. Although TeamViewer was not in wide operation in the company’s digital environment, it was not blocked by any of the legacy defenses.

The device then connected to an internal file server and downloaded 1.95 TB of data, and uploaded the same volume of data to pcloud[.]com. This exfiltration took place during work hours to blend in with regular admin activity.

The device was also seen downloading Rclone software – an open source tool, which was likely applied to sync data automatically to the legitimate file storage service pCloud.

The compromised admin credential allowed the threat actor to move laterally during this time. Following the completion of the data exfiltration, the device ‘serverps’ finally began encrypting files on 12 devices with the extension *.06d79000.

As with the majority of ransomware incidents, the encryption happened outside of office hours – overnight in local time – to minimize the chance of the security team responding quickly.

AI-powered investigation

Cyber AI Analyst reported on four incidents related to the attack, highlighting the suspicious behavior to the security team and providing a report on the affected devices for immediate remediation. Such concise reporting allowed the security team to quickly identify the scope of the infection and respond accordingly.

Figure 2: Cyber AI Analyst incident tray for a week

Cyber AI Analyst investigates on demand

Following further analysis on March 13, the security team employed Cyber AI Analyst to conduct on-demand investigations into the compromised admin credential in Microsoft 365, as well as another device which was identified as a potential threat.

Cyber AI Analyst created an incident for this other device, which resulted in the identification of unusual port scanning during the time period of infection. The device was promptly removed from the network.

Figure 3: Cyber AI Analyst incident for a compromised device, detailing an unusual internal download

Double trouble

The use of legitimate tools and ‘Living off the Land’ techniques (using RDP and a compromised admin credential) allowed the threat actors to carry out the bulk of the attack in less than 24 hours. By exploiting TeamViewer as a legitimate file storage solution for the data exfiltration, as opposed to relying on a known ‘bad’ or recently registered domain, the hackers easily circumvented all the existing signature-based defenses.

If Darktrace had not detected this intrusion and immediately alerted the security team, the attack could have resulted not only in a ‘denial of business’ with employees locked out of their files, but also in sensitive data loss. The AI went a step further in saving the team vital time with automatic investigation and on-demand reporting.

There is so much more to lose from double extortion ransomware. Exfiltration provides another layer of risk, leading to compromised intellectual property, reputational damage, and compliance fines. Once a threat group has your data, they might easily ask for more payments down the line. It is important therefore to defend against these attacks before they happen, proactively implementing cyber security measures that can detect and autonomously respond to threats as soon as they emerge.

Learn more about double extortion ransomware.

Darktrace model detections:

  • Device / Suspicious Network Scan Activity
  • Device / RDP Scan
  • Device / Network Scan
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous Connection / Unusual Admin RDP Session
  • Device / Multiple Lateral Movement Model Breaches
  • User / New Admin Credentials on Client
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Low and Slow Exfiltration
  • Device / Anomalous SMB Followed By Multiple Model
  • Anomalous Connection / Download and Upload
  • Anomalous Connection / Suspicious Activity On High Risk Device
  • Anomalous File / Internal::Additional Extension Appended to SMB File
  • Compromise / Ransomware::Suspicious SMB Activity
  • Anomalous Connection / Sustained MIME Type Conversion
  • Device / Anomalous RDP Followed By Multiple Model Breaches
  • Anomalous Connection / Suspicious Read Write Ratio
  • Device / Large Number of Model Breaches
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

More in this series

No items found.

Blog

/

/

September 17, 2026

The Problem of Re-defining Human Value in the Agentic Age

Default blog imageDefault blog image

Newsfeeds are constantly informing us about the rapid escalation of agentic AI systems. These systems move far beyond simple machine-based computations, and  the focused, defined and bounded assistance that most AI systems started out as.

The next evolution of AI will harness the agentic properties of orchestration, automation, and heightened value-chains in IT, taking on the burden of workflow management, not just workflow delivery.

In nearly all of these instances, promises are made such as ‘this will free up human time’ or ‘this will allow people to focus on higher-order strategy’. However that message is delivered, one thing is clear: in ceding the orchestration and management of work to increasingly sophisticated AI agents and agentic systems, human value will be elevated to a particular and specific layer: the ability to judge its outputs.  As AI takes on more tasks, humans should be able to focus on a higher level of governance; making sure the decisions that AI offers us are ethical, responsible and worthwhile.  

But there are two major problems with that approach.

This blog discusses the problem of how Agentic systems are re-shaping how we review information, where we fit in, and when we make decisions.  It also discusses the problem of how the increased flow of confident, generated information affects the way we make judgement.  This blog considers how human judgement needs to adapt, and how a behavioral defense approach – using techniques pioneered by Darktrace – can help us do that.

The challenge of knowing where human judgement belongs

As we confer more automated decision-making to agentic systems, it might look increasingly less like ‘granting permissions’, and more like ‘surrendering authority’.  

The judgement layer for AI-generated work is not a fixed boundary. We have become used to the idea of a ‘human in the loop’ (HITL) and, historically, relationships between humans and IT systems were reasonably clear and bounded.  Computer and software systems were programmed to carry out certain tasks or automated functions, and humans could control the gates and decision points where actions were undertaken. Even across highly complex computational workflows, human interaction was a controllable node within the process; we were able to configure and regulate. But in the agentic age, where that human interaction sits, and what it can influence shifts every time AI systems are granted autonomy.  

This leads us to the first problem: if humans are moving themselves (or are being moved) into the ‘judgement’ part of the value chain, exactly where and when do we exercise that judgement?  

Humans are no longer the sole shepherds of computer-based or software-controlled outputs.  We are at times at least one step further (and slower) behind the new agentic shepherds.  We might also be blind to what they are doing.  Not only might we be removed and blind to the actions of our AI shepherds, but with the challenge of unknown, unapproved AI systems operating beyond our control, humans might not even know that our work is being shepherded by an AI at all.  Simply put, with the advent of greater levels of autonomy and orchestration, humans are at risk of not even knowing where to apply our newly-extended powers of strategic judgement.

Shadow AI – the use of unapproved AI systems or processes – is a growing threat to the role of effective governance and oversight. Shadow AI isn't just the AI you can't see. Its the AI you already know about being used in an unapproved way. The ability to generate effective oversight of the AI systems you use (or that are used on your behalf) will be increasingly important to ensure that human judgement in the AI value chain is effective, and deliberately placed.

The problem of what makes good judgement

The second problem lies in how flawed human judgement can be.  Humans are historically, notoriously, and, sometimes dangerously, unreliable when it comes to exercising judgement.  Humans are prone to the worst kinds of bias, the seduction of malign influence, and the sometimes-overwhelming urge to succeed. AI has long had a known flaw of operating with sycophancy, providing outputs that tend to agree with or flatter the human user.  But as AI grows ever more effective, there is a risk of both hyper-enablement (where humans increasingly and knowingly enable AI despite potential harm), as well as the greater risk of suggestion. Both of these aspects could skew the newly-elevated input of human judgement.

Imagine a highly competent AI system that has just orchestrated and managed a dizzying array of processes and workflows.  The AI is designed to present the human decision-maker with recommendations; based on analysis, comparison and other programmed factors.  This is where the human judgement layer is enabled.  But what if that judgement is summarily diffused by an AI-based recommendation that emulates the decision, provides plausible but unattractive alternatives, then suggests (or, worse, directs) the human end-user to take a particular course of action.

The risk here is that you are given a recommendation, tailored to your preferences (which the AI has learned, or which you have divulged), and which appears to make perfect sense.  It appears to be a well-weighted recommendation, with sound arguments that tap into our inherent biases or inclinations so that a specific decision-path is followed. With the growth of agentic systems specifically designed to match user profiles (from Cowork agents to ‘digital twin’ models), the likelihood of agentic influence could badly skew human judgement or, at the least, devalue the proposition that humans are taking a higher-layer of strategic control over AI-based decisions.

If AI convincingly recommends something that may be problematic, it can be difficult to discern both accurate data, and the context required to make the right judgement.

Given the two problems described above, the job of exercising valuable human judgement in the agentic age can draw down to these two questions:

  • When should humans intervene in the agentic process?  
  • How can we make the best possible judgement calls?

What humans contribute that AI cannot

For all the flaws that make human judgement unreliable, people have the edge over even the most sophisticated and powerful AI systems when it comes to issues such as ethics and social context.  An AI system can, with startling granularity, rank the value of adopting a new business proposal: offering predictive metrics on costs, returns, market value, time-to-deliver operations, conformance with legal registers, etc.  But it can’t tell if the business proposal is ethically sound, or if the business venture will potentially affect groups outside of the analyzed proposal. It can’t tell you if the CEO has a ‘bad feeling’ about this effort.  It can’t tell you if this is the right thing to do.  

The ability to add social context, balance complex interpersonal dynamics, understand nuance, and to go beyond what seems economically reasonable is where human judgement can add value.  

Human judgement is difficult to encapsulate in metrics. And the way we train our development may need to adapt too. Rather than building up a gradual, experiential knowledge base, we should think about training the skill of judgement itself; especially for an agentic age.

How behavioral security strengthens AI governance

If this all feels like a vicious circle (‘I need AI help to make good judgements’ / ‘AI can twist what I need to judge’) it needn’t be. The key to this is having a defense-in-depth approach, with tools that can actually help.

This is precisely where behavioral security becomes important. The complex and nuanced way that humans exercise judgement is often rooted in our ability to recognize behavior that doesn't look right. We may not always be able to articulate it immediately, but we can often identify when an action, recommendation, or outcome feels inconsistent with the context around it. As AI systems take on more responsibility across the decision chain, preserving that ability to recognize meaningful deviations becomes increasingly important.

Darktrace’s / SECURE AI is designed to do exactly that. It applies behavioral security to AI ecosystems, helping organizations understand how people, AI tools, identities, and agents interact across the business. By learning the patterns of normal AI usage and surfacing activity that deviates from those patterns, it provides security teams with the context needed to investigate risk, understand unusual behavior, and make informed governance decisions. Rather than relying solely on predefined rules or assumptions, this behavioral understanding helps organizations distinguish between expected AI activity and behavior that warrants closer scrutiny.

This matters because we are already in an era of information overload. If humans are expected to elevate their value through strategic judgement, the ability to do this without being overwhelmed by data (good or bad) will be critical.  

We need the ability to discern when we're being misled by AI, and whether our judgement calls are being made on the basis of accurate, contextual information. Darktrace / SECURE AI provides that additional layer of defensive security for activity we cannot easily see. Whether it is suspected Shadow AI or skewed recommendations, the net result is a protected organization, where users can more effectively use AI to make positive judgements.

For those where that judgement is a critical skill (both individuals, as well as those working in security teams), improving our metacognition - the ability to understand information in a broader context - will supercharge the value of human judgement. When those judgements are grounded in context rather than assumptions we have better information to make sound decisions.

Conclusion

Human judgement is a skill that is honed over time and experience.  Darktrace’s / SECURE AI employs the same principles, but at machine-speed. Rather than influencing or directing, Darktrace / SECURE AI offers AI-enabled assurance; providing human-based judgement with the right context to make a balanced decision.  

What we judge can be valued by the legitimacy of its outputs. For AI, those outputs are valued on the speed and accuracy of the information provided.  Increasingly for humans, the value of our outputs will be based on the validity of our judgement, and how we justify our decisions in ways that engineer confidence.  

Humans often know more than we can express, while AI is prone to expressing more than it truly understands. Humans can bridge the context AI often fails to appreciate. When that judgement is supported by relevant, impartial AI systems, this is the future space where good AI governance will be exercised.

Discover Darktrace / SECURE AI.

[related-resource]

Continue reading
About the author
Jason Lusted
AI Governance Advisor

Blog

/

/

September 4, 2026

Darktrace Advances Incident Investigation and AI-Agent Security with OpenAI Daybreak Models

Default blog imageDefault blog image

Earlier this year, Darktrace joined OpenAI’s Daybreak Defense Network to explore how their cyber capabilities can be integrated within Darktrace products and services to transform how security teams move from signal to action.

At the heart of this work is Darktrace's behavioral understanding of customer environments and identification of complex security incidents, combined with OpenAI models that can add context to help explain why an incident matters and its potential impact on the business. By bringing these capabilities into defensive workflows security teams already use, the goal is to give defenders not just greater visibility, but the context and guidance they need to act with confidence.

Since joining the program, we've been working with OpenAI to explore how these capabilities can address specific security challenges for defenders.

The problem we're solving

Attackers continue to change how they operate, including by using AI to increase the speed and scale of some techniques. Security teams are already managing a large volume of alerts, and the question isn't just what's happening, but how it could affect the organization. Even when an incident is fully investigated and correlated, technical severity alone doesn't tell a security team how much it actually matters to the business. That same challenge extends to internal AI adoption. As organizations adopt more AI systems and agents, security teams need visibility into their behavior, access and activity, along with the broader business context needed to identify and investigate potential risk.

Darktrace's Adaptive AI™ builds a detailed, organization-specific picture of what's normal for each environment, and uses that picture to investigate threats and identify complex security activity across domains. OpenAI's models can build on Darktrace's correlated, technically prioritized incidents by adding context that can help defenders understand what may be at stake.

What we're building

Our work is focused on two areas: supporting security investigation and response, and helping defenders identify risky behavior across enterprise AI systems and agents.

The first aligns Darktrace's behavioral understanding with OpenAI models to support  security investigation and prioritization. Darktrace's Adaptive AI continuously learns the unique patterns of normal behavior within each customer it protects, creating a deep, organization-specific understanding of its digital estate. When unusual activity emerges, OpenAI's models can draw on that context to help analysts investigate the incident, understand its significance and assess potential business consequences — reducing the need to manually assemble context from fragmented signals.

Second, we are exploring how these capabilities can support AI-agent and runtime security through Darktrace / SECURE AI™. OpenAI’s Daybreak models can build on the detections and visibility Darktrace / SECURE AI provides, connecting signals across a customer's environment and help defenders identify potentially risky behavior involving AI systems and agents. Activity that might appear isolated can instead be connected with related signals, helping defenders investigate the broader context and determine appropriate remediation.

Darktrace brings deep cybersecurity expertise, an evolving understanding of each customer's environment, and AI-driven identification of threats across the digital estate. Through the Daybreak Defense Network, Darktrace is exploring how OpenAI models can augment those capabilities in defensive security workflows — supporting incident investigation and response and improving visibility into AI-agent and runtime risk.

These capabilities are still in development, and we're excited to continue building on this work.

To learn more about how Darktrace continues to innovate to meet today's most pressing security challenges, register for our upcoming launch broadcast here.

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI