To achieve compliance in 2020, human teams need artificial intelligence to make sense of their dynamic digital estates.
From credit card details and medical records, through to private conversations and even dating preferences, the modern consumer entrusts an unprecedented number of organizations with their most sensitive information, hoping against hope that it will be stored on the digital equivalent of Fort Knox.
The reality, however, is that robust data privacy has thus far proven elusive. Almost 13 billion records were breached over the last two years — including from Facebook, Google, and the US Postal Service — demonstrating once again that no network perimeter can keep motivated attackers at bay.
For governments whose principal responsibility is to safeguard their citizens, implementing a strong data protection regime is therefore as challenging as it is critical. At a time when cyber-criminals find vulnerabilities in the most ostensibly airtight systems, these regulators have tended to shy away from mandating concrete security practices, since no one can anticipate which measures will repel the next unpredictable attack. Instead, most data protection laws default to ambiguous calls for “reasonable,” “adequate,” or “appropriate” cyber defenses — language that arguably renders any breached company noncompliant by definition.
While such ambiguity makes prediction pieces like this one speculative to some extent, the coming year will almost certainly witness both an increase in data protection laws around the world as well as a less forgiving interpretation of their requirements. Ultimately, as governments attempt to address growing public concern over data privacy, the mere fact of having suffered a breach could be seen as grounds for significant fines. Avoiding these fines — and doing right by one’s customers — entails assuming that the bad guys will inevitably get past the perimeter.
Figure 1: Noncompliance penalties are only getting larger as the 2020s near. Data source: CSO.
GDPR goes global
The EU’s adoption of the General Data Protection Regulation (GDPR) in April 2016 was the watershed moment in the history of data protection legislation. Its enumeration of individual privacy rights, its 72-hour breach notification requirement, and its broad data protection directives continue to serve as a blueprint for countless others, such as Brazil’s General Data Protection Law (LGPD), Thailand’s Personal Data Protection Act (PDPA), and the California Consumer Privacy Act (CCPA). All three of these regulations become enforceable in 2020, with major ramifications for companies worldwide.
Brazil’s law, which will go into effect on August 15, 2020, is modeled closely after GDPR. Like GDPR, the law applies to all companies that handle the personal data of any of Brazil’s 210 million residents — regardless of where these companies themselves are headquartered. Also like GDPR, of course, the LGPD’s security clauses are open to interpretation. The law compels data handlers to “adopt security, technical, and administrative measures able to protect personal data from unauthorized access,” taking into account “the current state of technology.”
The PDPA in Thailand — effective starting on May 27, 2020 — is similarly vague in mandating unspecified security measures. It parts company, however, in that violators face the possibility of criminal prosecution and even imprisonment for up to one year, in addition to civil damages. Organizations classified as Critical Information Infrastructure (CII), including banks, telecoms, utilities, and hospitals, are regulated under Thailand’s separate Cybersecurity Act and its slightly more detailed obligations.
Figure 2: New GDPR-inspired laws like Brazil’s will turn this map increasingly blue. Image source: DLA Piper.
In California, meanwhile, the CCPA will enforce noncompliance penalties of up to $750 per consumer per incident beginning on the first day of 2020, which could result in multibillion-dollar fines in the case of large-scale breaches. Such precise provisions indicate that GDPR-style legislation is more than a symbolic step toward data protection. And yet, as of August 2019, only 2% of companies reported that they were fully compliant with CCPA, perhaps because, according to a state-commissioned study, California firms will be forced to shell out $55 billion on just their initial compliance efforts.
Checkmate for checkbox compliance
Between the hundreds of data protection fines levied under GDPR and analogous laws, the common thread is that penalized companies are deemed to have suffered a preventable breach. For instance, in the aftermath of the 2017 Equifax compromise that exposed the personal information of more than 140 million consumers, the company was found to have been in violation of the FTC Safeguards Rule, which compelled it to adopt security measures “appropriate to [the] size and complexity” of its digital infrastructure. The US government concluded that the incident was “entirely preventable” had Equifax performed a “routine” security update on the impacted database — an oversight that precipitated at least $1.4 billion in total damages.
However, a closer inspection reveals challenges far deeper than just a simple oversight. Equifax did indeed scan its network for vulnerabilities, but the automated scanner it used was not properly configured to search all of its assets. The truth is that these kinds of misconfigurations and blind spots are a symptom of the conventional approach to cyber security itself, an approach reliant on humans to adjust and monitor a vast array of siloed security tools. In the context of cloud environments designed to be dynamic and IoT devices that are often unbeknownst to the security team, there is nothing routine about defending the “size and complexity” of the modern enterprise.
The upshot of all these new laws, requirements, and fines is that the days of mere checkbox compliance are over. Breached companies can no longer throw up their hands and point to the list of perimeter security tools they had in place, particularly because attackers largely exploit user errors and misconfigurations that — while inevitable — also appear preventable in a vacuum. Rather, to achieve compliance in 2020, human teams need artificial intelligence to make sense of their dynamic digital estates. By learning how each unique user and device normally functions while ‘on the job’, such Cyber AI detects threats that are already inside the perimeter — before they cost the company in court.
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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)
Get the latest insights on emerging cyber threats
Attackers are adapting, are you ready? This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.
Identity-based attacks: How attackers are bypassing traditional defenses
Zero-day exploitation: The rise of previously unknown vulnerabilities
AI-driven threats: How adversaries are leveraging AI to outmaneuver security controls
RansomHub Ransomware: investigación de Darktrace sobre la herramienta más nueva en 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)
Get the latest insights on emerging cyber threats
Attackers are adapting, are you ready? This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.
Identity-based attacks: How attackers are bypassing traditional defenses
Zero-day exploitation: The rise of previously unknown vulnerabilities
AI-driven threats: How adversaries are leveraging AI to outmaneuver security controls
