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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.
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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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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
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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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December 22, 2025

The Year Ahead: AI Cybersecurity Trends to Watch in 2026

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Introduction: 2026 cyber trends

Each year, we ask some of our experts to step back from the day-to-day pace of incidents, vulnerabilities, and headlines to reflect on the forces reshaping the threat landscape. The goal is simple:  to identify and share the trends we believe will matter most in the year ahead, based on the real-world challenges our customers are facing, the technology and issues our R&D teams are exploring, and our observations of how both attackers and defenders are adapting.  

In 2025, we saw generative AI and early agentic systems moving from limited pilots into more widespread adoption across enterprises. Generative AI tools became embedded in SaaS products and enterprise workflows we rely on every day, AI agents gained more access to data and systems, and we saw glimpses of how threat actors can manipulate commercial AI models for attacks. At the same time, expanding cloud and SaaS ecosystems and the increasing use of automation continued to stretch traditional security assumptions.

Looking ahead to 2026, we’re already seeing the security of AI models, agents, and the identities that power them becoming a key point of tension – and opportunity -- for both attackers and defenders. Long-standing challenges and risks such as identity, trust, data integrity, and human decision-making will not disappear, but AI and automation will increase the speed and scale of the cyber risk.  

Here's what a few of our experts believe are the trends that will shape this next phase of cybersecurity, and the realities organizations should prepare for.  

Agentic AI is the next big insider risk

In 2026, organizations may experience their first large-scale security incidents driven by agentic AI behaving in unintended ways—not necessarily due to malicious intent, but because of how easily agents can be influenced. AI agents are designed to be helpful, lack judgment, and operate without understanding context or consequence. This makes them highly efficient—and highly pliable. Unlike human insiders, agentic systems do not need to be socially engineered, coerced, or bribed. They only need to be prompted creatively, misinterpret legitimate prompts, or be vulnerable to indirect prompt injection. Without strong controls around access, scope, and behavior, agents may over-share data, misroute communications, or take actions that introduce real business risk. Securing AI adoption will increasingly depend on treating agents as first-class identities—monitored, constrained, and evaluated based on behavior, not intent.

-- Nicole Carignan, SVP of Security & AI Strategy

Prompt Injection moves from theory to front-page breach

We’ll see the first major story of an indirect prompt injection attack against companies adopting AI either through an accessible chatbot or an agentic system ingesting a hidden prompt. In practice, this may result in unauthorized data exposure or unintended malicious behavior by AI systems, such as over-sharing information, misrouting communications, or acting outside their intended scope. Recent attention on this risk—particularly in the context of AI-powered browsers and additional safety layers being introduced to guide agent behavior—highlights a growing industry awareness of the challenge.  

-- Collin Chapleau, Senior Director of Security & AI Strategy

Humans are even more outpaced, but not broken

When it comes to cyber, people aren’t failing; the system is moving faster than they can. Attackers exploit the gap between human judgment and machine-speed operations. The rise of deepfakes and emotion-driven scams that we’ve seen in the last few years reduce our ability to spot the familiar human cues we’ve been taught to look out for. Fraud now spans social platforms, encrypted chat, and instant payments in minutes. Expecting humans to be the last line of defense is unrealistic.

Defense must assume human fallibility and design accordingly. Automated provenance checks, cryptographic signatures, and dual-channel verification should precede human judgment. Training still matters, but it cannot close the gap alone. In the year ahead, we need to see more of a focus on partnership: systems that absorb risk so humans make decisions in context, not under pressure.

-- Margaret Cunningham, VP of Security & AI Strategy

AI removes the attacker bottleneck—smaller organizations feel the impact

One factor that is currently preventing more companies from breaches is a bottleneck on the attacker side: there’s not enough human hacker capital. The number of human hands on a keyboard is a rate-determining factor in the threat landscape. Further advancements of AI and automation will continue to open that bottleneck. We are already seeing that. The ostrich approach of hoping that one’s own company is too obscure to be noticed by attackers will no longer work as attacker capacity increases.  

-- Max Heinemeyer, Global Field CISO

SaaS platforms become the preferred supply chain target

Attackers have learned a simple lesson: compromising SaaS platforms can have big payouts. As a result, we’ll see more targeting of commercial off-the-shelf SaaS providers, which are often highly trusted and deeply integrated into business environments. Some of these attacks may involve software with unfamiliar brand names, but their downstream impact will be significant. In 2026, expect more breaches where attackers leverage valid credentials, APIs, or misconfigurations to bypass traditional defenses entirely.

-- Nathaniel Jones, VP of Security & AI Strategy

Increased commercialization of generative AI and AI assistants in cyber attacks

One trend we’re watching closely for 2026 is the commercialization of AI-assisted cybercrime. For example, cybercrime prompt playbooks sold on the dark web—essentially copy-and-paste frameworks that show attackers how to misuse or jailbreak AI models. It’s an evolution of what we saw in 2025, where AI lowered the barrier to entry. In 2026, those techniques become productized, scalable, and much easier to reuse.  

-- Toby Lewis, Global Head of Threat Analysis

Conclusion

Taken together, these trends underscore that the core challenges of cybersecurity are not changing dramatically -- identity, trust, data, and human decision-making still sit at the core of most incidents. What is changing quickly is the environment in which these challenges play out. AI and automation are accelerating everything: how quickly attackers can scale, how widely risk is distributed, and how easily unintended behavior can create real impact. And as technology like cloud services and SaaS platforms become even more deeply integrated into businesses, the potential attack surface continues to expand.  

Predictions are not guarantees. But the patterns emerging today suggest that 2026 will be a year where securing AI becomes inseparable from securing the business itself. The organizations that prepare now—by understanding how AI is used, how it behaves, and how it can be misused—will be best positioned to adopt these technologies with confidence in the year ahead.

Learn more about how to secure AI adoption in the enterprise without compromise by registering to join our live launch webinar on February 3, 2026.  

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December 22, 2025

Why Organizations are Moving to Label-free, Behavioral DLP for Outbound Email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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