How Autonomous Response AI is Winning Automated Extortion
19
Jun 2019
Darktrace, creator of the first enterprise-grade autonomous response technology, leverages AI algorithms to stop malware in its tracks. Learn more here!
Just threat detection is not enough
At a time when automated cyber-attacks execute at machine speed, the reality is that merely detecting these attacks is no longer sufficient to stop them before the damage is done. According to the Ponemon Institute’s oft-cited study on the topic, US companies take an average of 206 days to identify a data breach. And even when security teams discover a potential compromise the moment it begins, human professionals are fundamentally overmatched by malicious code that can encrypt or exfiltrate data in under a minute.
In this era of fast-acting threats, the only way forward is to fight code with code, to pit algorithm against algorithm, and to counter machine-speed attacks with machine-speed defenses. Darktrace, creator of the first enterprise-grade autonomous response technology, leverages AI algorithms to stop malware in its tracks, allowing incident responders to investigate and take action at their own pace. And critically, Darktrace safeguards the digital estate day and night, weekend and holiday, because cyber-criminals don’t wait until business hours to strike.
Examined below are three sophisticated attacks that Darktrace neutralized on behalf of security teams that were either out of office or unable to react in time. Collectively, they demonstrate that the future of autonomous cyber defense has already arrived.
Automated extortion, absent security team
The quintessential example of a cyber-threat too rapid for human professionals to parry, ransomware has become a top-of-mind concern for organizations around the world. In fact, previous research has found that approximately 70% of companies simply hand over the ransom upon getting hit, regardless of the cost. However, Darktrace's Autonomous Response prevents ransomware from spreading by confining users and devices to their typical ‘patterns of life’. Rooted in a constantly refined understanding of ‘self’ versus ‘not self’, Darktrace AI surgically intervenes to shut off just the anomalous activity, while still allowing business operations to continue uninterrupted.
At 7:05 pm on a Friday, an employee at a large telecommunications firm accessed his personal email from a corporate smartphone and was tricked into downloading a malicious file that contained ransomware. Seconds later, the device began connecting to an external server on the Tor network — executing the attack just after the company’s security team had left the office for the weekend.
Darktrace AI, meanwhile, responded nine seconds after encryption began, raising a prioritized alert that called for immediate action. As the behavior persisted over the next few seconds, Darktrace activated AI-enabled autonomous response, which interrupted all attempts to write encrypted files before the ransomware spread across the telecom’s network. Critically, the autonomous response technology was on guard, even when the security team couldn’t be.
Darktrace anticipates the alphabet
Nearly 95% of all successful cyber-attacks begin with a phishing email, which dupe employees into breaching their organizations before the security team realizes that anything is wrong. Even more difficult to catch are personalized “spear phishing” emails that use reconnaissance gathered from either social media or physical surveillance to impersonate trusted colleagues. Thwarting an advanced spear phishing campaign requires understanding normal behavior for each user well enough to flag subtly suspicious emails, as well as the ability to autonomously disable their malicious links — a combination that only Darktrace AI has achieved.
On the network of a major US city, a sophisticated spear phishing campaign managed to bypass the city’s native email controls. The attackers, who had obtained the city’s address book, were emailing recipients alphabetically, from “A” to “Z,” with ostensibly harmless emails that contained a malicious payload. Despite the well-disguised nature of this attack, Darktrace immediately flagged the domain linked in the emails as abnormal for the city’s employees, an action only possible with the evolving understanding of ‘self’ that Darktrace AI learns.
Darktrace's Autonomouse Response was deployed in ‘Passive Mode’ at the time, a trust-building setting that restricts the AI to communicating what it would have done in response to the threat rather than actually interceding. Interestingly enough, however, this nuance served to demonstrate the technology’s ability to stop attacks that conventional tools miss. Whereas Darktrace detected the campaign at the letter “A,” the city’s array of legacy tools finally woke up to the threat at “R.” In ‘Active Mode’, Darktrace would have neutralized the attack before it reached a single user.
Serious threat at amusement park
Data exfiltration is among the most common objectives of cyber-criminals today, as stolen personal information and credentials can be sold on the Dark Web, used to commit identity theft, or leveraged to move laterally within a victim’s network. At a North American amusement park, an advanced attacker targeted an IoT device — a physical locker designed to store personal belongings — in an attempt to exfiltrate such data. As part of its default setting, the ‘smart’ locker regularly established contact with the supplier’s third-party online platform, a process that the attackers hijacked to compromise the device.
Once infiltrated, the locker started to transfer more than a gigabyte of unencrypted data across the network to a rare external site. The connections, which likely included identifying details and sensitive credentials, had the potential to be transmitted over the internet entirely unprotected — allowing the attackers to intercept the connections and use the information to breach the company’s network perimeter.
Due to the severity of the threat, Darktrace determined that an autonomous response was required. Within seconds, Darktrace AI took action by intelligently blocking all outgoing connections from the compromised locker. In doing so, it gave ample time for the security team to remove the smart locker from the internet — before any sensitive company or consumer data could be exfiltrated.
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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.
Author
Justin Fier
SVP, Red Team Operations
Justin is one of the US’s leading cyber intelligence experts, and holds the position of SVP, Red Team Operations at Darktrace. His insights on cyber security and artificial intelligence have been widely reported in leading media outlets, including the Wall Street Journal, CNN, The Washington Post, and VICELAND. With over 10 years’ experience in cyber defense, Justin has supported various elements in the US intelligence community, holding mission-critical security roles with Lockheed Martin, Northrop Grumman Mission Systems and Abraxas. Justin is also a highly-skilled technical specialist, and works with Darktrace’s strategic global customers on threat analysis, defensive cyber operations, protecting IoT, and machine learning.
Bytesize Security: Insider Threats in Google Workspace
What is an insider threat?
An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.
Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.
For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.
Attack overview: Insider threat
In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.
While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.
In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.
Conclusion
Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.
Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.
Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)
Appendices
Darktrace Model Detections
SaaS / Resource::Unusual Download Of Externally Shared Google Workspace File
RansomHub Ransomware: Darktrace’s Investigation of the Newest Tool in ShadowSyndicate's Arsenal
What is ShadowSyndicate?
ShadowSyndicate, also known as Infra Storm, is a threat actor reportedly active since July 2022, working with various ransomware groups and affiliates of ransomware programs, such as Quantum, Nokoyawa, and ALPHV. This threat actor employs tools like Cobalt Strike, Sliver, IcedID, and Matanbuchus malware in its attacks. ShadowSyndicate utilizes the same SSH fingerprint (1ca4cbac895fc3bd12417b77fc6ed31d) on many of their servers—85 as of September 2023. At least 52 of these servers have been linked to the Cobalt Strike command and control (C2) framework [1].
What is RansomHub?
First observed following the FBI's takedown of ALPHV/BlackCat in December 2023, RansomHub quickly gained notoriety as a Ransomware-as-a-Service (RaaS) operator. RansomHub capitalized on the law enforcement’s disruption of the LockBit group’s operations in February 2024 to market themselves to potential affiliates who had previously relied on LockBit’s encryptors. RansomHub's success can be largely attributed to their aggressive recruitment on underground forums, leading to the absorption of ex-ALPHV and ex-LockBit affiliates. They were one of the most active ransomware operators in 2024, with approximately 500 victims reported since February, according to their Dedicated Leak Site (DLS) [2].
ShadowSyndicate and RansomHub
External researchers have reported that ShadowSyndicate had as many as seven different ransomware families in their arsenal between July 2022, and September 2023. Now, ShadowSyndicate appears to have added RansomHub’s their formidable stockpile, becoming an affiliate of the RaaS provider [1].
Darktrace’s analysis of ShadowSyndicate across its customer base indicates that the group has been leveraging RansomHub ransomware in multiple attacks in September and October 2024. ShadowSyndicate likely shifted to using RansomHub due to the lucrative rates offered by this RaaS provider, with affiliates receiving up to 90% of the ransom—significantly higher than the general market rate of 70-80% [3].
In many instances where encryption was observed, ransom notes with the naming pattern “README_[a-zA-Z0-9]{6}.txt” were written to affected devices. The content of these ransom notes threatened to release stolen confidential data via RansomHub’s DLS unless a ransom was paid. During these attacks, data exfiltration activity to external endpoints using the SSH protocol was observed. The external endpoints to which the data was transferred were found to coincide with servers previously associated with ShadowSyndicate activity.
Darktrace’s coverage of ShadowSyndicate and RansomHub
Darktrace’s Threat Research team identified high-confidence indicators of compromise (IoCs) linked to the ShadowSyndicate group deploying RansomHub. The investigation revealed four separate incidents impacting Darktrace customers across various sectors, including education, manufacturing, and social services. In the investigated cases, multiple stages of the kill chain were observed, starting with initial internal reconnaissance and leading to eventual file encryption and data exfiltration.
Attack Overview
Internal Reconnaissance
The first observed stage of ShadowSyndicate attacks involved devices making multiple internal connection attempts to other internal devices over key ports, suggesting network scanning and enumeration activity. In this initial phase of the attack, the threat actor gathers critical details and information by scanning the network for open ports that might be potentially exploitable. In cases observed by Darktrace affected devices were typically seen attempting to connect to other internal locations over TCP ports including 22, 445 and 3389.
C2 Communication and Data Exfiltration
In most of the RansomHub cases investigated by Darktrace, unusual connections to endpoints associated with Splashtop, a remote desktop access software, were observed briefly before outbound SSH connections were identified.
Following this, Darktrace detected outbound SSH connections to the external IP address 46.161.27[.]151 using WinSCP, an open-source SSH client for Windows used for secure file transfer. The Cybersecurity and Infrastructure Security Agency (CISA) identified this IP address as malicious and associated it with ShadowSyndicate’s C2 infrastructure [4]. During connections to this IP, multiple gigabytes of data were exfiltrated from customer networks via SSH.
Data exfiltration attempts were consistent across investigated cases; however, the method of egress varied from one attack to another, as one would expect with a RaaS strain being employed by different affiliates. In addition to transfers to ShadowSyndicate’s infrastructure, threat actors were also observed transferring data to the cloud storage and file transfer service, MEGA, via HTTP connections using the ‘rclone’ user agent – a command-line program used to manage files on cloud storage. In another case, data exfiltration activity occurred over port 443, utilizing SSL connections.
Lateral Movement
In investigated incidents, lateral movement activity began shortly after C2 communications were established. In one case, Darktrace identified the unusual use of a new administrative credential which was quickly followed up with multiple suspicious executable file writes to other internal devices on the network.
The filenames for this executable followed the regex naming convention “[a-zA-Z]{6}.exe”, with two observed examples being “bWqQUx.exe” and “sdtMfs.exe”.
Figure 1: Cyber AI Analyst Investigation Process for the SMB Writes of Suspicious Files to Multiple Devices' incident.
Additionally, script files such as “Defeat-Defender2.bat”, “Share.bat”, and “def.bat” were also seen written over SMB, suggesting that threat actors were trying to evade network defenses and detection by antivirus software like Microsoft Defender.
File Encryption
Among the three cases where file encryption activity was observed, file names were changed by adding an extension following the regex format “.[a-zA-Z0-9]{6}”. Ransom notes with a similar naming convention, “README_[a-zA-Z0-9]{6}.txt”, were written to each share. While the content of the ransom notes differed slightly in each case, most contained similar text. Clear indicators in the body of the ransom notes pointed to the use of RansomHub ransomware in these attacks. As is increasingly the case, threat actors employed double extortion tactics, threatening to leak confidential data if the ransom was not paid. Like most ransomware, RansomHub included TOR site links for communication between its "customer service team" and the target.
Figure 2: The graph shows the behavior of a device with encryption activity, using the “SMB Sustained Mimetype Conversion” and “Unusual Activity Events” metrics over three weeks.
Since Darktrace’s Autonomous Response capability was not enabled during the compromise, the ransomware attack succeeded in its objective. However, Darktrace’s Cyber AI Analyst provided comprehensive coverage of the kill chain, enabling the customer to quickly identify affected devices and initiate remediation.
Figure 3: Cyber AI Analyst panel showing the critical incidents of the affected device from one of the cases investigated.
In lieu of Autonomous Response being active on the networks, Darktrace was able to suggest a variety of manual response actions intended to contain the compromise and prevent further malicious activity. Had Autonomous Response been enabled at the time of the attack, these actions would have been quickly applied without any human interaction, potentially halting the ransomware attack earlier in the kill chain.
Figure 4: A list of suggested Autonomous Response actions on the affected devices."
Conclusion
The Darktrace Threat Research team has noted a surge in attacks by the ShadowSyndicate group using RansomHub’s RaaS of late. RaaS has become increasingly popular across the threat landscape due to its ease of access to malware and script execution. As more individual threat actors adopt RaaS, security teams are struggling to defend against the increasing number of opportunistic attacks.
For customers subscribed to Darktrace’s Security Operations Center (SOC) services, the Analyst team promptly investigated detections of the aforementioned unusual and anomalous activities in the initial infection phases. Multiple alerts were raised via Darktrace’s Managed Threat Detection to warn customers of active ransomware incidents. By emphasizing anomaly-based detection and response, Darktrace can effectively identify devices affected by ransomware and take action against emerging activity, minimizing disruption and impact on customer networks.
Credit to Kwa Qing Hong (Senior Cyber Analyst and Deputy Analyst Team Lead, Singapore) and Signe Zahark (Principal Cyber Analyst, Japan)
