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October 20, 2021

How Ryuk Ransomware Has Made a Comeback

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20
Oct 2021
Discover how small-time criminals are getting ahold of Ryuk ransomware, and what organizations can do to protect themselves.

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 They are not known for using outdated tools.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.
Author
Brianna Leddy
Director of Analysis

Based in San Francisco, Brianna is Director of Analysis at Darktrace. She joined the analyst team in 2016 and has since advised a wide range of enterprise customers on advanced threat hunting and leveraging Self-Learning AI for detection and response. Brianna works closely with the Darktrace SOC team to proactively alert customers to emerging threats and investigate unusual behavior in enterprise environments. Brianna holds a Bachelor’s degree in Chemical Engineering from Carnegie Mellon University.

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November 28, 2024

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Cloud

Cloud security: addressing common CISO challenges with advanced solutions

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Cloud adoption is a cornerstone of modern business with its unmatched potential for scalability, cost efficiency, flexibility, and net-zero targets around sustainability. However, as organizations migrate more workloads, applications, and sensitive data to the cloud it introduces more complex challenges for CISO’s. Let’s dive into the most pressing issues keeping them up at night—and how Darktrace / CLOUD provides a solution for each.

1. Misconfigurations: The Silent Saboteur

Misconfigurations remain the leading cause of cloud-based data breaches. In 2023 alone over 80%  of data breaches involved data stored in the cloud.1  Think open storage buckets or overly permissive permissions; seemingly minor errors that are easily missed and can snowball into major disasters. The fallout of breaches can be costly—both financially and reputationally.

How Darktrace / CLOUD Helps:

Darktrace / CLOUD continuously monitors your cloud asset configurations, learning your environment and using these insights to flag potential misconfigurations. New scans are triggered when changes take place, then grouped and prioritised intelligently, giving you an evolving and prioritised view of vulnerabilities, best practice and mitigation strategies.

2. Hybrid Environments: The Migration Maze

Many organizations are migrating to the cloud, but hybrid setups (where workloads span both on-premises and cloud environments) create unique challenges and visibility gaps which significantly increase complexity. More traditional and most cloud native security tooling struggles to provide adequate monitoring for these setups.

How Darktrace / CLOUD Helps:

Provides the ability to monitor runtime activity for both on-premises and cloud workloads within the same user interface. By leveraging the right AI solution across this diverse data set, we understand the behaviour of your on-premises workloads and how they interact with cloud systems, spotting unusual connectivity or data flow activity during and after the migration process.

This unified visibility enables proactive detection of anomalies, ensures seamless monitoring across hybrid environments, and provides actionable insights to mitigate risks during and after the migration process.

3. Securing Productivity Suites: The Last Mile

Cloud productivity suites like Microsoft 365 (M365) are essential for modern businesses and are often the first step for an organization on a journey to Infrastructure as a Service (IaaS) or Platform as a Service (PaaS) use cases. They also represent a prime target for attackers. Consider a scenario where an attacker gains access to an M365 account, and proceeds to; access sensitive emails, downloading files from SharePoint, and impersonating the user to send phishing emails to internal employees and external partners. Without a system to detect these behaviours, the attack may go unnoticed until significant damage is done.

How Darktrace helps:

Darktrace’s Active AI platform integrates with M365 and establishes an understanding of normal business activity, enabling the detection of abnormalities across its suite including Email, SharePoint and Teams. By identifying subtle deviations in behaviour, such as:

   •    Unusual file accesses

   •    Anomalous login attempts from unexpected locations or devices.

   •    Suspicious email forwarding rules created by compromised accounts.

Darktrace’s Autonomous Response can act precisely to block malicious actions, by disabling compromised accounts and containing threats before they escalate. Precise actions also ensure that critical business operations are maintained even when a response is triggered.  

4. Agent Fatigue: The Visibility Struggle

To secure cloud environments, visibility is critical. If you don’t know what’s there, how can you secure it? Many solutions require agents to be deployed on every server, workload, and endpoint. But managing and deploying agents across sprawling hybrid environments can be both complex and time-consuming when following change controls, and especially as cloud resources scale dynamically.

How Darktrace / CLOUD Helps:

Darktrace reduces or eliminates the need for widespread agent deployment. Its agentless by default, integrating directly with cloud environments and providing instant visibility without the operational headache. Darktrace ensures coverage with minimal friction. By intelligently graphing the relationships between assets and logically grouping your deployed Cloud resources, you are equipped with real-time visibility to quickly understand and protect your environment.

So why Darktrace / CLOUD?

Darktrace’s Self-Learning AI redefines cloud security by adapting to your unique environment, detecting threats as they emerge, and responding in real-time. From spotting misconfigurations to protecting productivity suites and securing hybrid environments. Darktrace / CLOUD simplifies cloud security challenges without adding operational burdens.

From Chaos to Clarity

Cloud security doesn’t have to be a game of endless whack-a-mole. With Darktrace / CLOUD, CISOs can achieve the visibility, control, and proactive protection they need to navigate today’s complex cloud ecosystems confidently.

[1] https://hbr.org/2024/02/why-data-breaches-spiked-in-2023

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About the author
Adam Stevens
Director of Product, Cloud Security

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November 27, 2024

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Inside the SOC

Behind the veil: Darktrace's detection of VPN exploitation in SaaS environments

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Introduction

In today’s digital landscape, Software-as-a-Service (SaaS) platforms have become indispensable for businesses, offering unparalleled flexibly, scalability, and accessibly across locations. However, this convenience comes with a significant caveat - an expanded attack surface that cyber criminals are increasingly exploiting. In 2023, 96.7% of organizations reported security incidents involving at least one SaaS application [1].

Virtual private networks (VPNs) play a crucial role in SaaS security, acting as gateways for secure remote access and safeguarding sensitive data and systems when properly configured. However, vulnerabilities in VPNs can create openings for attacks to exploit, allowing them to infiltrate SaaS environments, compromise data, and disrupt business operations. Notably, in early 2024, the Darktrace Threat Research team investigated the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPNs, which would allow threat actors to gain access to sensitive systems and execute remote code.

More recently, in August, Darktrace identified a SaaS compromise where a threat actor logged into a customer’s VPN from an unusual IP address, following an initial email compromise. The attacker then used a separate VPN to create a new email rule designed to obfuscate the phishing campaign they would later launch.

Attack Overview

The initial attack vector in this case appeared to be through the customer’s email environment. A trusted external contact received a malicious email from another mutual contact who had been compromised and forwarded it to several of the organization’s employees, believing it to be legitimate. Attackers often send malicious emails from compromised accounts to their past contacts, leveraging the trust associated with familiar email addresses. In this case, that trust caused an external victim to unknowingly propagate the attack further. Unfortunately, an internal user then interacted with a malicious payload included in the reply section of the forwarded email.

Later the same day, Darktrace / IDENTITY detected unusual login attempts from the IP 5.62.57[.]7, which had never been accessed by other SaaS users before. There were two failed attempts prior to the successful logins, with the error messages “Authentication failed due to flow token expired” and “This occurred due to 'Keep me signed in' interrupt when the user was signing in.” These failed attempts indicate that the threat actor may have been attempting to gain unauthorized access using stolen credentials or exploiting session management vulnerabilities. Furthermore, there was no attempt to use multi-factor authentication (MFA) during the successful login, suggesting that the threat actor had compromised the account’s credentials.

Following this, Darktrace detected the now compromised account creating a new email rule named “.” – a telltale sign of a malicious actor attempting to hide behind an ambiguous or generic rule name.

The email rule itself was designed to archive incoming emails and mark them as read, effectively hiding them from the user’s immediate view. By moving emails to the “Archive” folder, which is not frequently checked by end users, the attacker can conceal malicious communications and avoid detection. The settings also prevent any automatic deletion of the rules or forced overrides, indicating a cautious approach to maintaining control over the mailbox without raising suspicion. This technique allows the attacker to manipulate email visibility while maintaining a façade of normality in the compromised account.

Email Rule:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: .
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace further identified that this email rule had been created from another IP address, 95.142.124[.]42, this time located in Canada. Open-source intelligence (OSINT) sources indicated this endpoint may have been malicious [2].

Given that this new email rule was created just three minutes after the initial login from a different IP in a different country, Darktrace recognized a geographic inconsistency. By analyzing the timing and rarity of the involved IP addresses, Darktrace identified the likelihood of malicious activity rather than legitimate user behavior, prompting further investigation.

Figure 1: The compromised SaaS account making anomalous login attempts from an unusual IP address in the US, followed by the creation of a new email rule from another VPN IP in Canada.

Just one minute later, Darktrace observed the attacker sending a large number of phishing emails to both internal and external recipients.

Figure 2: The compromised SaaS user account sending a high volume of outbound emails to new recipients or containing suspicious content.

Darktrace / EMAIL detected a significant spike in inbound emails for the compromised account, likely indicating replies to phishing emails.

Figure 3: The figure demonstrates the spike in inbound emails detected for the compromised account, including phishing-related replies.

Furthermore, Darktrace identified that these phishing emails contained a malicious DocSend link. While docsend[.]com is generally recognized as a legitimate file-sharing service belonging to Dropbox, it can be vulnerable to exploitation for hosting malicious content. In this instance, the DocSend domain in question, ‘hxxps://docsend[.]com/view/h9t85su8njxtugmq’, was flagged as malicious by various OSINT vendors [3][4].

Figure 4: Phishing emails detected containing a malicious DocSend link.

In this case, Darktrace Autonomous Response was not in active mode in the customer’s environment, which allowed the compromise to escalate until their security team intervened based on Darktrace’s alerts. Had Autonomous Response been enabled during the incident, it could have quickly mitigated the threat by disabling users and inbox rules, as suggested by Darktrace as actions that could be manually applied, exhibiting unusual behavior within the customer’s SaaS environment.

Figure 5: Suggested Autonomous Response actions for this incident that required human confirmation.

Despite this, Darktrace’s Managed Threat Detection service promptly alerted the Security Operations Center (SOC) team about the compromise, allowing them to conduct a thorough investigation and inform the customer before any further damage could take place.

Conclusion

This incident highlights the role of Darktrace in enhancing cyber security through its advanced AI capabilities. By detecting the initial phishing email and tracking the threat actor's actions across the SaaS environment, Darktrace effectively identified the threat and brought it to the attention of the customer’s security team.

Darktrace’s proactive monitoring was crucial in recognizing the unusual behavior of the compromised account. Darktrace / IDENTITY detected unauthorized access attempts from rare IP addresses, revealing the attacker’s use of a VPN to hide their location.

Correlating these anomalies allowed Darktrace to prompt immediate investigation, showcasing its ability to identify malicious activities that traditional security tools might miss. By leveraging AI-driven insights, organizations can strengthen their defense posture and prevent further exploitation of compromised accounts.

Credit to Priya Thapa (Cyber Analyst), Ben Atkins (Senior Model Developer) and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Models

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compromise / High Priority New Email Rule
  • SaaS / Compromise / New Email Rule and Unusual Email Activity
  • SaaS / Compromise / Unusual Login and Outbound Email Spam
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
  • SaaS / Email Nexus / Possible Outbound Email Spam

Autonomous Response Models

  • Antigena / SaaS / Antigena Email Rule Block
  • Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Technique Name Tactic ID Sub-Technique of

  • Cloud Accounts. DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS T1078.004 T1078
  • Compromise Accounts RESOURCE DEVELOPMENT T1586
  • Email Accounts RESOURCE DEVELOPMENT T1586.002 T1586
  • Internal Spearphishing LATERAL MOVEMENT T1534 -
  • Outlook Rules PERSISTENCE T1137.005 T1137
  • Phishing INITIAL ACCESS T1566 -

Indicators of Compromise (IoCs)

IoC – Type – Description

5.62.57[.]7 – Unusual Login Source

95.142.124[.]42– IP – Unusual Source for Email Rule

hxxps://docsend[.]com/view/h9t85su8njxtugmq - Domain - Phishing Link

References

[1] https://wing.security/wp-content/uploads/2024/02/2024-State-of-SaaS-Report-Wing-Security.pdf

[2] https://www.virustotal.com/gui/ip-address/95.142.124.42

[3] https://urlscan.io/result/0caf3eee-9275-4cda-a28f-6d3c6c3c1039/

[4] https://www.virustotal.com/gui/url/8631f8004ee000b3f74461e5060e6972759c8d38ea8c359d85da9014101daddb

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About the author
Priya Thapa
Cyber Analyst
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